AUTHOR OF THIS BLOG

DR ANTHONY MELVIN CRASTO, WORLDDRUGTRACKER
Dec 082017
 

 

A practical synthesis of 2,3-dihydro-1,5-benzothiazepines

Green Chem., 2017, 19,5703-5707
DOI: 10.1039/C7GC02097J, Paper
Domenico C. M. Albanese, Nicoletta Gaggero, Meng Fei
Hexafluoro-2-propanol as the solvent allows a catalyst free domino approach to 2,3-dihydro-1,5-benzothiazepines in up to 98% yield.

A practical synthesis of 2,3-dihydro-1,5-benzothiazepines

*Corresponding authors

LocationMilano, Italy
Positionassociate professor

Domenico Albanese received his Ph.D. degree in 1993 with Prof. Dario Landini working on phase transfer catalysis. After short stays at Imperial College London and the Technical University of Denmark, he gained a permanent position at the Università degli Studi di Milano, where he was appointed associate professor in 2008. His research interests include novel developments of phase-transfer catalysis, green chemistry and the development of new environmentally friendly antifouling agents.

University of Milan

image file: c4ra11206g-p2.tif

image file: c4ra11206g-p2.tifNicoletta Gaggero Nicoletta Gaggero received her Ph.D. degree in 1992 working on stereoselective reactions with natural proteins, enzymes and models of enzymes. After working at the Laboratoire de Chimie de Coordination du CNRS of Toulouse, she obtained a permanent position at the Università degli Studi di Milano. Her research interests cover the field of biocatalysis and asymmetric synthesis.

Abstract

2,3-Dihydro-1,5-benzothiazepines have been obtained through a domino process involving a Michael addition of 2-aminothiophenols to chalcones, followed by in situ cyclization. Up to 98% chemical yields have been obtained at room temperature under essentially neutral conditions by using hexafluoro-2-propanol as an efficient medium.

http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC02097J?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

2,4-Diphenyl-2,3-dihydro-1,5-benzothiazepine (4a)
Yellow solid; mp 114-116 C [lit.1 , 114-115 °C], AcOEt/PE 1:9. 1H NMR (300 MHz, CDCl3,): 3.07 (t, J = 12.6 Hz, 1 H), 3.32 (dd, J = 4.7, 13.1 Hz, 1 H), 4.99 (dd, J = 4.5, 12.0 Hz, 1 H), 7.12-7.17 (m, 1 H), 7.25-7.30 (m, 5 H), 7.44-7.51 (m, 4 H), 7.62 (d, J = 6.1 Hz, 2 H), 8.06 (d, J = 7.5 Hz, 2 H). Isolated Yield: 339 mg, 86%.
2-(4-Hydroxyphenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine (4e)
Light brown solid; mp 131-134 °C. AcOEt/PE 40:60.
1H NMR (CDCl3, 300 MHz):  = 3.01 (t, J = 12.7 Hz, 1 H), 3.28 (dd, J = 4.8, 12.9 Hz, 1 H), 4.95 (dd, J = 4.7, 12.5 Hz, 1 H), 5.10 (bs, 1 H), 6.76 (d, J = 8.5 Hz, 2 H), 7.18-7.21 (m, 3 H), 7.35 (d, J = 8.5 Hz, 1 H), 7.46- 7.55 (m, 4 H), 7.63 (dd, J =1.5, 7.7 Hz, 1 H), 8.06 (m, 2 H).
13C NMR (CDCl3, 75 MHz): 37.99 (CH2), 60.07 (CH), 115.53 (CH), 123.08 (C), 127.40 (CH), 128.79 (CH), 131.17 (CH), 136.54 (C), 141.59 (C), 155.24 (C). IR (KBr): 1599, 2921, 3350 cm-1 .
MS (ESI): m/z= 332.24 (MH)+ .
Anal. Calcd. for C21H17NOS: C, 76.10; H, 5.17; N, 4.23, found: C, 76.21; H, 5.15; N, 4.24.
Isolated Yield: 360 mg, 87%.
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“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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Dec 062017
 

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2073844-77-4
C24 S12, 673.04
Coroneno[1,​12-​cd:2,​3-​cd‘:4,​5-​cd”:6,​7-​c”’d”’:8,​9-​c””d””:10,​11-​c””’d””’]​hexakis[1,​2]​dithiole

A persulfurated coronene, a molecule dubbed a “sulflower” for its resemblance to a sunflower, bloomed this year. It’s the first fully sulfur-substituted polycyclic aromatic hydrocarbon and only the second member of a new class of circular heterocyclic carbon sulfide compounds, after the synthesis of octathio[8]circulene a decade ago.

Chemists hope to create other class members, including the simplest one, persulfurated benzene, for use in battery cathodes and other electronic materials.

A team led by Xinliang Feng of Dresden University of Technology and Klaus Müllen of the Max Planck Institute for Polymer Research created the sulflower (J. Am. Chem. Soc. 2017, DOI: 10.1021/jacs.6b12630).

http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630

 

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Synthesis of persulfuratedcoronene (5, PSC)

5 (82 mg) as dark red solid in 61% yield. HR-MS (HR-MALDI-TOF) m/z: Calcd. for C24S12: 671.6629; Found 671.6648 [M]+; Elem. Anal. calcd. for C24S12: C, 42.83; S, 57.17. Found: C, 42.87; S, 57.13.

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Persulfurated Coronene: A New Generation of “Sulflower”

 Department of Chemistry and Food Chemistry, Center for Advancing Electronics Dresden, Technische Universität Dresden, 01062 Dresden, Germany
§ Max-Planck-Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
 Institute for Materials Science, Max Bergmann Center of Biomaterials, and Center for Advancing Electronics Dresden, TU Dresden, 01069 Dresden, Germany
 Dipartimento di Chimica, Materiali ed Ingegneria Chimica ‘G. Natta’, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133 Milano, Italy
J. Am. Chem. Soc.2017139 (6), pp 2168–2171
DOI: 10.1021/jacs.6b12630
Publication Date (Web): January 27, 2017
Copyright © 2017 American Chemical Society
Abstract Image

We report the first synthesis of a persulfurated polycyclic aromatic hydrocarbon (PAH) as a next-generation “sulflower.” In this novel PAH, disulfide units establish an all-sulfur periphery around a coronene core. The structure, electronic properties, and redox behavior were investigated by microscopic, spectroscopic and electrochemical methods and supported by density functional theory. The sulfur-rich character of persulfurated coronene renders it a promising cathode material for lithium–sulfur batteries, displaying a high capacity of 520 mAh g–1 after 120 cycles at 0.6 C with a high-capacity retention of 90%

Renhao Dong

Image result for Renhao Dong DRESDEN

Research Group Leader

Renhao received his PhD in Physical Chemistry from Shandong University in 2013. Since 01/2017, he is a research group leader at the Chair for Molecular Functional Materials in TUD. His current research interest focuses on synthesis of organic 2D crystals (2D polymers/COFs/MOFs) and their applications in electronics and energy technology.

Contact

Phone: +49 – 351 / 463-40401 or -34932
Email: renhao.dong@tu-dresden.de

Prof. Xinliang Feng

Prof. Xinliang Feng

Work Biography:

This is a professorship in the context of the cluster of excellence cfaed.

Xinliang Feng received his Bachelor’s degree in analytic chemistry in 2001 and Master’s degree in organic chemistry in 2004. Then he joined Prof. Klaus Müllen’s group at the Max Planck Institute for Polymer Research for PhD thesis, where he obtained his PhD degree in April 2008. In December 2007 he was appointed as a group leader at the Max-Planck Institute for Polymer Research and in 2012 he became a distinguished group leader at the Max-Planck Institute for Polymer Research.

His current scientific interests include graphene, two-dimensional nanomaterials, organic conjugated materials, and carbon-rich molecules and materials for electronic and energy-related applications. He has published more than 370 research articles which have attracted more than 25000 citations with H-index of 75.

He has been awarded several prestigious prizes such as IUPAC Prize for Young Chemists (2009), Finalist of 3rd European Young Chemist Award, European Research Council (ERC) Starting Grant Award (2012), Journal of Materials Chemistry Lectureship Award (2013), ChemComm Emerging Investigator Lectureship (2014), Highly Cited Researcher (Thomson Reuters, 2014, 2015 and 2016), Fellow of the Royal Society of Chemistry (FRSC, 2014). He is an Advisory Board Member for Advanced Materials, Journal of Materials Chemistry A, ChemNanoMat, Energy Storage Materials, Small Methods and Chemistry -An Asian Journal. He is also one of the Deputy Leaders for European communitys pilot project Graphene Flagship, Head of ESF Young Research Group “Graphene Center Dresden”, and Working Package Leader of WP Functional Foams & Coatings of GRAPHENE FLAGSHIP.

Academic Employment

  • 12/2007-12/2012: Group Leader, Max Planck Institute for Polymer Research in Mainz, Germany
  • 06/2010: Director of the Institute of Advanced Organic Materials, Shanghai Jiao Tong University
  • 03/2011: Distinguished Adjunct Professorship in Shanghai Jiao Tong University, Chin
  • 12/2012-07/2014: Distinguished Group Leader, Max Planck Institute for Polymer Research in Mainz, Germany
  • 08/2014: W3 Chair Professor, Technische Universität Dresden, Germany

Honors and Duties

  • Marie Currie Fellowship (2005-2006)
  • Chinese Government Award for Outstanding Self-financed Students (2008)
  • IUPAC Prize for Young Chemists (2009)
  • Finalist of 3rd European Young Chemist Award (2010)
  • ISE (International Society of Electrochemistry) Young Investigator Award (2011)
  • Adjunct Professorship, China University of Geosciences (Wuhan) (2011)
  • Deputy Leader of one of the ten European representatives of the European community’s pilot project GRAPHENE FLAGSHIP (2012)
  • EU FET Young Explorer (2012)
  • ERC Starting Grant Award (2012)
  • Advisory Board Member for Advanced Materials (2013)
  • Journal of Materials Chemistry Lectureship Award (2013)
  • Advisory Board Member for Journal of Materials Chemistry A (2014)
  • Editorial Board Member of Chemistry – An Asian Journal (2014)
  • ChemComm Emerging Investigator Lectureship (2014)
  • Highly Cited Researcher (Thomson Reuters, 2014)
  • Fellow of the Royal Society of Chemistry (2014)
  • Highly Cited Researcher (Chemistry and Materials Science) (2015)
  • International Advisory Board of Energy Storage Materials (2015)
  • International Advisory Board of ChemNanoMat (2015)
  • Highly Cited Researcher (Chemistry and Materials Science, Thomson Reuters) (2016)
  • Head of ESF Young Research Group “Graphene Center Dresden” (2016)
  • Working Package Leader of WP Functional Foams & Coatings of GRAPHENE FLAGSHIP (2016)
  • International Advisory Board of Small Methods (2016)
  • Path Leader of 2.5D path within the cluster of excellence CFAED (2016)
  • ERC Proof-of-Concept Project Award (2017)
  • Small Young Innovator Award (2017)
  • Hamburg Science Award (2017)

Referee for:

Nature, Science, Nature Materials, Nature Nanotechnology, Nature Chemistry, Journal of the American Chemical Society, Angewandte Chemie International Edition, Nano Letters, Advanced Materials, Chemical Society Reviews, ACS Nano, Small, Chemical Communications, Chemistry of Materials, Organic Letters, Journal of the Organic Chemistry, Chemistry – A European Journal, ChemSusChem, ChemPhysChem, Macromolecular Rapid Communications, Journal of Material Chemistry, New Journal of Chemistry, Chemistry – An Asian Journal, ACS Applied Materials & Interfaces, Energy & Environmental Science, Organic Electronics and so on

Referee for research grants in NSF, US Department of Energy, ESF, ISF and Fondazione Cariparo and Fondazione CariModena.

Publications

Click to open publications list

Contact (Secretariat)

Phone: +49 351 / 463-43251
Fax: +49 351 / 463-43268
Email: sabine.strecker@tu-dresden.de

 

 

 

 

Klaus Müllen
Max-Planck-Institute for Polymer Research, Mainz, 55128, Germany
vyrez_DSC_3783.JPG

Research into energy technologies and electronic devices is strongly governed by the available materials. We introduce a synthetic route to graphenes which is based upon the cyclodehydrogenation (“graphitization”) of well-defined dendritic (3D) polyphenylene precursors. This approach is superior to physical methods of graphene formation such as chemical vapour deposition or exfoliation in terms of its (i) size and shape control, (ii) structural perfection, and (iii) processability (solution, melt, and even gas phase). The most convincing case is the synthesis of graphene nanoribbons under surface immobilization and in-situ control by scanning tunnelling microscopy.
Columnar superstructures assembled from these nanographene discs serve as charge transport channels in electronic devices. Field-effect transistors (FETs), solar cells, and sensors are described as examples.
Upon pyrolysis in confining geometries or “carbomesophases”, the above carbon-rich 2D- and 3D- macromolecules transform into unprecedented carbon materials and their carbon-metal nanocomposites. Exciting applications are shown for energy technologies such as battery cells and fuel cells. In the latter case, nitrogen-containing graphenes serve as catalysts for oxygen reduction whose efficiency is superior to that of platinum.

Müllen, K., Rabe, J.R., Acc. Chem. Res. 2008, 41, (4), 511-520;
Wang, X., Zhi, L., Müllen, K. Nano. Lett. 2008, 8, 323-327;
Feng, X.; Chandrasekhar, N.; Su, H. B.; Müllen, K., Nano. Lett. 2008, 8, 4259.;
Pang, S.; Tsao, H. N.; Feng, X.; Müllen, K., Adv. Mater. 2009, 31, 3488;
Feng, X., Marcon, V., Pisula, W., Hansen, M.R., Kirkpatrick, I., Müllen, K., Nature Mater. 2009, 8, 421;
Cai, J., Ruffieux, P., Jaafar, R., Bieri, M., Braun, T., Blankenburg, S., Muoth, M., Seitsonen, A. P., Saleh, M., Feng, X., Müllen, K., Fasel, R., Nature 2010, 466, 470-473;
Yang, S., Feng, X., Zhi, L., Cao, Q., Maier, J., Müllen, K., Adv. Mater. 2010, 22, 838; Liu, R., Wu, D., Feng, X., Müllen, K., Angew. Chem. Int. Ed. 2010, 49, 2565;
Käfer, D., Bashir, A., Dou, X., Witte, G., Müllen, K., Wöll, C., Adv. Mater. 2010, 22, 384;
Diez-Perez, I., Li, Z., Hihath, J., Li, J., Zhang, C., X., Zang, L., Dai, Y., Heng, X., Müllen, K., Tao, N. J. Nature Commun. 2010, DOI: 10.1038.

Prof. Dr. Klaus Müllen
joined the Max-Planck-Society in 1989 as one of the directors of the Max-Planck Institute for Polymer Research. He obtained a Diplom-Chemiker degree at the University of Cologne in 1969 after work with Professor E. Vogel. His Ph.D. degree was granted by the University of Basel, Switzerland, in 1972 where he undertook research with Professor F. Gerson on twisted pi-systems and EPR spectroscopic properties of the corresponding radical anions. In 1972 he joined the group of Professor J.F.M. Oth at the Swiss Federal Institute of Technology in Zürich where he worked in the field of dynamic NMR spectroscopy and electrochemistry. He received his habilitation from the ETH Zürich in 1977 and was appointed Privatdozent. In 1979 he became a Professor in the Department of Organic Chemistry, University of Cologne, and accepted an offer of a chair in Organic Chemistry at the University of Mainz in 1983. He received a call to the University of Göttingen in 1988.

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S1Sc6c8c1c9SSc%10c2SSc%13c2c%11c4c3c%13SSc3c%12SSc7c%12c4c(c5c7SSc56)c8c%11c9%10

http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630

https://cen.acs.org/articles/95/i49/molecules-of-the-year-2017.html?utm_source=Twitter&utm_medium=Social&utm_campaign=CEN&hootPostID=ea1deb5464b6231122901a3321f4ff5e

 

“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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Nov 212017
 

Graphical abstract: Highly active, separable and recyclable bipyridine iridium catalysts for C–H borylation reactions

Highly active, separable and recyclable bipyridine iridium catalysts for C–H borylation reactions

Abstract

Iridium complexes generated from Ir(I) precursors and PIB oligomer functionalized bpy ligands efficiently catalyzed the reactions of arenes with bis(pinacolato)diboron under mild conditions to produce a variety of arylboronate compounds. The activity of this PIB bound homogeneous catalyst is similar to that of an original non-recyclable catalyst which allows it to be used under milder conditions than other reported recyclable catalysts. This oligomer-supported Ir catalyst was successfully recovered through biphasic extraction and reused for eight cycles without a loss of activity. Biphasic separation after the initial use of the catalyst led to an insignificant amount of iridium leaching from the catalyst to the product, and no iridium leaching from the catalyst was observed in the subsequent recycling runs. Arylboronate products obtained after extraction are sufficiently pure as observed by 1H and 13C-NMR spectroscopy that they do not require further purification.

Hind MAMLOUK, PhD

Hind MAMLOUK, PhD

R&D in Organic Materials Chemistry Looking for a New Challenge
Texas A&M University
3-Chloro-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anisole (5). Transparent oil. Yield: 87%.
1H NMR (600 MHz, CDCl3) δ 7.37 (s, 1H), 7.22 – 7.16 (m, 1H), 6.99 (s, 1H), 3.82 (s, 3H), 1.34 (s, 12H);
13C NMR (101 MHz, CDCl3) δ 159.88, 134.57, 126.84, 117.71, 117.43, 84.15, 55.52, 24.82.
GCMS: RT=14.55 min, M+ = 268.1 vs MW= 268.54 g.mol-1 .
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Image result for Sherzod T. Madrahimov Texas A&M University at Qatar

Sherzod Madrahimov

Asst. Prof.

Research experience

  • Aug 2015–present
    Asst. Prof.
    Texas A&M University at Qatar · Chemistry
    Qatar · Doha
  • Jul 2012–Jul 2015
    PostDoc Position
    Northwestern University · Department of Chemistry
    United States · Evanston
  • Aug 2007–Jul 2012
    Graduate student
    University of Illinois, Urbana-Champaign · Department of Chemistry
    United States · Urbana

Image result for Texas A&M University at Qatar

Texas A&M University at Qatar

 

A headshot

David Bergbreiter
Professor

Contact

Department of Chemistry
Texas A&M University
College Station, TX 77843-3255

P: 979-845-3437
F: 979-845-4719
bergbreiter@chem.tamu.edu

Current Activities

Our group explores new chemistry related to catalysis and polymer functionalization using the tools and precepts of synthetic organic chemistry to prepare functional oligomers or polymers that in turn are used to either effect catalysis in a greener, more environmentally benign way or to more efficiently functionalize polymers. Often this involves creatively combining the physiochemical properties of a polymer with the reactivity of a low molecular weight compound to form new materials with new functions. These green chemistry projects involve undamental research both in synthesis and catalysis but has practical aspects because of its relevance to practical problems.

A common theme in our catalysis studies is exploring how soluble polymers can facilitate homogeneous catalysis. Homogeneous catalysts are ubiquitously used to prepare polymers, chemical intermediates, basic chemicals and pharmaceuticals. Such catalysts often use expensive or precious metals or expensive ligands or are used at relatively high catalyst loadings. The products often contain traces of these catalysts or ligands – traces that are undesirable for esthetic reasons or because of the potential toxicity of these impurities. Both the cost of these catalysts of these issues require catalyst/product separation – separations that often are inefficient and lead to chemical waste. These processes also use volatile organic solvents – solvents that have to be recovered and separated. Projects underway in our lab explore how soluble polymers can address each of these problems. Examples of past schemes that achieve this goal in a general way as highlighted in the Figure below.

We also use functional polymers to modify existing polymers. Ongoing projects involve molecular design of additives that can more efficiently modify polymers’ physical properties. We also use functional polymers in covalent layer-by-layer assembly to surface polymers’ surface chemistry. An example of this work is our use of ‘smart’ polymers that reversibly change from being water soluble cold to being insoluble and hydrophobic on heating. Such polymers’ have been used by us to prepare ‘smart’ catalysts, ‘smart’ surfaces and membranes, and to probe fundamental chemistry underlying temperature and salt-dependent protein solvation.

Jakkrit Suriboot

Jakkrit Suriboot

Research Assistant at Texas A&M University
Image result for Praveen Kumar Manyam TEXAS

Dr. Praveen Kumar

Title: Research Assistant Professor

Education: M.S., I.I.T. Roorkee
Ph.D., Panjab University Chandigarh (2008)
Visiting Fellow (w/ Prof. G. G. Balint-Kurti), Bristol University, UK
Postdoctoral Research Associate (w/ Prof. Svetlana Malinovskaya), Stevens Institute of Technology, Hoboken, NJ
Senior Postdoctoral Research Associate (w/ Prof. Seogjoo Jang), Queens College of CUNY, NY

Office: Chemistry 010

Phone: 806-742-3124

Email: praveen.kumar@ttu.edu

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“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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Gram-Scale Synthesis of Amines Bearing a gem-Difluorocyclopropane Moiety

 organic chemistry, spectroscopy, SYNTHESIS  Comments Off on Gram-Scale Synthesis of Amines Bearing a gem-Difluorocyclopropane Moiety
Nov 102017
 
Image result for ukraine flag animated

Image result for National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine

Ukraine

original image

 

Abstract

The synthesis of monocyclic, spirocyclic and fused bicyclic secondary amines bearing a gem-difluorocyclopropane moiety via difluorocyclopropanation of unsaturated N-Boc derivatives using the trifluoromethyl(trimethyl)silane/sodium iodide [CF3SiMe3-NaI] system is described. The relative order of the substrate reactivity is established. It is shown that for the reactive alkenes the standard reaction conditions can be used, whereas for the substrates with low reactivity, slow addition of the Ruppert–Prakash reagent is necessary.

Gram-Scale Synthesis of Amines Bearing a gem-Difluorocyclopropane Moiety

Authors., Pavel S. Nosik,

DOI: 10.1002/adsc.201700857

Pavel S. Nosik,a.b Andrii O. Gerasov,a Rodion O. Boiko,a Eduard Rusanov,b Sergey V. Ryabukhin,c Oleksandr O. Grygorenko,c * Dmitriy M. Volochnyukb

a Spectrum Info Ltd., Life Chemicals Inc., Murmanska Street 5, Kyiv 02094, Ukraine

b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv 02660, Ukraine

c National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine

Image result for National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine

* Corresponding author. E-mail: gregor@univ.kiev.ua.

 

Oleksandr Grygorenko at National Taras Shevchenko University of Kyiv

Oleksandr Grygorenko

Ph D
Professor (Associate)
National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine
National Taras Shevchenko University of Kyiv

Image result for Dmitriy M. Volochnyuk

Dmitriy M. Volochnyuk

Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv 02660, Ukraine

Dmitriy M. Volochnyuk was born in 1980 in Irpen, Kyiv region, Ukraine. He graduated from Kyiv State Taras Shevchenko University in 2002 and was awarded his M.S. degree in chemistry. He received his Ph.D. in organic chemistry in 2005 from the Institute of Organic Chemistry, National Academy of Sciences of Ukraine under the supervision of Dr. A. Kostyuk for research on the chemistry of enamines. At present, he divides his time between the Institute of Organic Chemisty, as Deputy Head of Organophosphorus Department and Senior Researcher, and Enamine Ltd (Kyiv, Ukraine), as Director of Chemistry. His main scientific interests are related to fluoroorganic, organophosphorus, heterocyclic and combinatorial chemistry, and multistep organic synthesis. He is a coauthor of more than 80 papers

institute-of-organic-chemstry-nanu

 

  • Given that the incorporation of small fluorinated fragments in drug-like molecules continues to rise, this has created an onus on the synthetic community to provide robust, scalable routes to these molecules of interest. Grygorenko and co-workers have reported on a synthesis of amines featuring a gem-difluorocyclopropane moiety using the readily available Ruppert–Prakash reagent ( Adv. Synth. Catal. 201710.1002/adsc.201700857).
  • Evaluating a series of olefins under the standard reaction conditions in refluxing THF indicated that only the most reactive olefins (gem-disubstituted) provided good yields of the desired cyclopropane, while other solvents proved to be ineffective. Conducting a control experiment omitting the substrate demonstrated that the key issue herein was competitive decomposition of the TMSCF3 to a series of gaseous byproducts under the reaction conditions.
  • Whereas continuous flow provides a potential to mitigate against this, the current report demonstrated that slow addition of the reagent to the reaction mixture also provided a practical solution to this problem.
  • Employing this approach enabled not only excellent conversions and yields to be realized but also allowed reactivity trends to be identified. In general, gem-disubstituted are the most reactive with the trend correlating with steric hindrance.
  • For other classes of olefins, electronics are the major factor with the ability of the substituents to stabilize a positive charge in the transition state consistent with a nonsynchronous formation of the two sigma bonds in the cycloaddition the key consideration. The removal of the Boc-protecting group under standard acidic conditions provided the amines as their hydrochloride salts.
  • Eduard Rusanov at Institute of Organic Chemistry National Academy of Sciences of Ukraine
  • Eduard Rusanov

    PhD
    Head of Crystallographic Lab./Director of the crystallographic facility Nat. Acad. of Sci. Ukraine ‘Single Mjlecule Crystallography’ at IOC
    Institute of Organic Chemistry… · DEPARTMENT OF PHYSICOCHEMICAL INVESTIGATIONS

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tert-Butyl 1,1-difluoro-6-azaspiro[2.5]octane-6-carboxylate (10a):

Yield: 66.7 g (91%) (Method A); off-white crystalline powder: mp 46–48 8C;

1H NMR (CDCl3 , 400 MHz): d= 3.57–3.42 (m, 2H), 3.40–3.27 (m, 2H), 1.66–1.47 (m, 4H), 1.44 (s, J=2.3 Hz, 9H), 1.08 (t, J=8.3 Hz, 2H);

13C NMR (CDCl3, 101 MHz): d=154.2, 115.4 (t, J=288.1 Hz), 79.3, 42.8, 28.4, 28.1, 26.8 (t, J=10.0 Hz), 21.0 (t, J=10.1 Hz);

19F NMR (CDCl3 , 376 MHz): d=@140.6;

MS (EI): m/z= 247 (M+ ), 192 (M+@t-Bu), 174 (M+@t-BuO), 147 (M+@Boc), 127 (M+@Boc@HF);

Anal. calcd. for C12H19F2NO2 : C 58.29, H 7.74, N 5.66; found: C 58.49, H 8.02, N 5.30.

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2-Phenylfuran

 spectroscopy, SYNTHESIS  Comments Off on 2-Phenylfuran
Nov 092017
 

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2-Phenylfuran

17113-33-6 cas

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2-Phenylfuran (3v) [15]: According to the general procedure I and purification by column chromatography (100% PE) yielded 3v (35.9 mg, 50%) and the general procedure II yielded 3s (35.1 mg, 49%) as a white solid . 1 H NMR (400 MHz, CDCl3) δ 7.68-7.66 (m 2H), 7.46 (s, 1H), 7.40-7.35 (m, 2H), 7.26-7.23 (m, 1H), 6.645-6.639 (m, 1H), 6.461-6.457 (m, 1H). LRMS (ESI) calcd for [M+H]+ C10H9O 145.1, found 145.1.

15 Zhou, C.-Y.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2006, 8, 325.

Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, 199 RenAi Road, Suzhou, Jiangsu 215123, China
Org. Lett.201315 (11), pp 2664–2667
DOI: 10.1021/ol400946k

Abstract

Abstract Image

Direct arylation of unactivated arenes or heteroarenes with aryl halides could be carried out in the presence of potassium tert-butoxide and dimethyl sulfoxide under visible-light irradiation. Ir(ppy)3was found to be an effective photoredox catalyst for this reaction. The reactions of aryl iodides occurred at room temperature. Elevated temperature was required for aryl bromides. Homolytic aromatic substitution was proposed to be the operative reaction pathway.

Predicts

1H NMR

STR1

13C NMR

STR2

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http://pubs.acs.org/doi/10.1021/ol400946k

more info

Open Babel bond-line chemical structure with annotated hydrogens.<br>Click to toggle size.

<sup>1</sup>H NMR spectrum of C<sub>10</sub>H<sub>8</sub>O<sub></sub> in CDCL3 at 400 MHz.<br>Click to toggle size.

Shifts

Index Name Shift (ppm)
19 H7 6.582
1 H1 7.655
5 H5 7.655
15 H6 6.885
11 H2 7.415
7 H4 7.415
9 H3 7.362
17 H8 7.471

“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents

 spectroscopy, SYNTHESIS, Uncategorized  Comments Off on Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents
Nov 092017
 

Zhong-Xia WANG

STR1

 

STR1

N,N-dimethyl-4-biphenylamine

Molecular Formula, C14H15N
Molecular Weight, 197.28
CAS Number, 1137-79-7

(1) N,N-dimethyl-[1,1′-biphenyl]-4-amine (3a) 5,6

Elute: EtOAc/petroleum ether: 1/100 (v/v), white solid, yield 97.8 mg (99%).

1H NMR (400 MHz, CDCl3): δ 7.56 (d, J = 7.8 Hz, 2H), 7.51 (d, J = 8.8 Hz, 2H), 7.40 (t, J = 7.7 Hz, 2H), 7.30–7.21 (m, 1H), 6.81 (d, J = 8.8 Hz, 2H), 3.00 (s, 6H).

13C NMR (101 MHz, CDCl3): δ 150.09, 141.34, 129.37, 128.78, 127.84, 126.43, 126.12, 112.90, 40.97.

5 Yang, X.; Wang, Z.-X. Organometallics 2014, 33, 5863.

(6) Stibingerova, I.; Voltrova, S.; Kocova, S.; Lindale, M.; Srogl, J. Org. Lett. 2016, 18, 312.

STR1 STR2

 

Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents

Bo Yang and Zhong-Xia Wang* 
 CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China
 Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China
Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.7b03145

Abstract

Abstract Image

Cross-coupling of (hetero)arylthiols with arylzinc reagents via C–S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.

In summary, we developed a transition-metal-free coupling reaction of (hetero)arylthiols with arylzinc reagents to form bi(hetero)aryls. The reaction exhibited wide substrate scope and good compatibility of functional groups. Electron-rich and -poor aryl or heteroaryl thiols can be converted. Various arylzinc reagents, including electron-rich and electron-poor reagents, can be employed as the coupling partners. Preliminary mechanistic studies suggest a nucleophilic aromatic substitution pathway, and Mg2+ and Li+ ions play important roles in the process of reaction. This study provides an example of S2– as a leaving group in an aromatic system and an effective methodology for the synthesis of bi(hetero)aryls including pharmaceutical molecules without transition-metal impurities.

Zhong-Xia WANG

Department: Department of Chemistry
Mailing Address:
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Rd, Hefei, Anhui, 230026, PR China
Postal Code:
230026
Phone:
+86-551-63603043
Fax:
Homepage:
http://chem.ustc.edu.cn/szdw_16/bd/201210/t20121023_142877.html
Zhong-Xia Wang is a professor in the Department of Chemistry at the University of Science and Technology 
of China. He received his BS degree (1983) and MS degree (1986) from Nankai University, 
and PhD degree (1997) from the University of Sussex, UK. Since July 1986, Wang has been working 
at the University of Science and Technology of China (USTC) successively as Assistant, 
Lecturer, Associate Professor, and Professor. From Aug. 1993 to Oct. 1996, he pursued his doctoral 
studies at the University of Sussex, UK, and from Oct. 1999 to Oct. 2000, he was a Research Associate 
at the Chinese University of Hong Kong.

 学 系
Department of Chemistry

Predicts

STR1

STR1

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http://pubs.acs.org/doi/10.1021/acs.orglett.7b03145

 

“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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Benzisoxazole: a privileged scaffold for medicinal chemistry

 new drugs, organic chemistry, SYNTHESIS, Uncategorized  Comments Off on Benzisoxazole: a privileged scaffold for medicinal chemistry
Nov 082017
 

 

Med. Chem. Commun., 2017, Advance Article
DOI: 10.1039/C7MD00449D, Review Article
K. P. Rakesh, C. S. Shantharam, M. B. Sridhara, H. M. Manukumar, Hua-Li Qin
The benzisoxazole analogs represent one of the privileged structures in medicinal chemistry and there has been an increasing number of studies on benzisoxazole-containing compounds.

Benzisoxazole: a privileged scaffold for medicinal chemistry

 

Abstract

The benzisoxazole analogs represent one of the privileged structures in medicinal chemistry and there has been an increasing number of studies on benzisoxazole-containing compounds. The unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on. This review examines the state of the art in medicinal chemistry as it relates to the comprehensive and general summary of the different benzisoxazole analogs, their use as starting building blocks of multifarious architectures on scales sufficient to drive human drug trials. The number of reports describing benzisoxazole-containing highly active compounds leads to the expectation that this scaffold will further emerge as a potential candidate in the field of drug discovery.

Hua-Li Qin

Dr. Hua-Li Qin Ph. D 2009
qinhuali@bu.edu

Department of Pharmaceutical Engineering, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, PR China

  • Wuhan University of Technology

Hua-Li joined the Panek group in 2005.

C. S. Shantharam at Pooja Bhagavat Memorial Mahajana P.G Centre

C. S. Shantharam

M.Sc., Ph.D
Assistant professor
Pooja Bhagavat Memorial Mahaja… , Mysore · Department of Chemistry
Department of Chemistry, Pooja Bhagavath Memorial Mahajana Education Centre, Mysuru-570016, India
Image result for Department of Chemistry, Pooja Bhagavat Memorial Mahajana Education Centre, Mysore-570016, India
Image result for Department of Chemistry, Pooja Bhagavat Memorial Mahajana Education Centre, Mysore-570016, India

Hua-Li Qin

 

Manukumar H M at University of Mysore

Manukumar H M

Master of Science
Research Scholar

 

////////////Benzisoxazole, scaffold, medicinal chemistry

“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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Metal-free synthesis of polysubstituted pyrroles using surfactants in aqueous medium

 organic chemistry, SYNTHESIS  Comments Off on Metal-free synthesis of polysubstituted pyrroles using surfactants in aqueous medium
Nov 072017
 

 

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC01874F, Communication
Amrendra Kumar, Ramanand, Narender Tadigoppula
An efficient and metal-free method has been developed for the synthesis of polysubstituted pyrrole derivatives with combination of sodium dodecyl sulphate (SDS) and Triton X-100 surfactants using water as a solvent at room temperature in 2-6 h and under microwave conditions (10 min) with good to excellent yields.

Metal-free synthesis of polysubstituted pyrroles using surfactants in aqueous medium

Image result for Narender Tadigoppula

Dr. Narender Tadigoppula

Principal Scientist
Medicinal & Process Chemistry
Central Drug Research Institute
India

Dr. Narender Tadigoppula is currently principal scientist in the department of medicine chemistry central drug research institute. He published more than 30 research articles. His major major research activities are identification of biologically active lead molecules through activity guided fraction and isolation work on the medicinal plants, marine organisms and microorganisms for metabolic diseases (hyperglycemia, dyslipidemia), parasitic diseases (leishmania and malaria), cancer etc., and chemical transformation of natural products of biological importance to improve their potency. We synthesize these biologically active lead molecules and their analogues in our laboratory. We have identified several lead molecules from the Indian medicinal plants for various disease areas as described below and further work is in progress to develop natural products based drugs.

Abstract

An efficient and metal-free method has been developed for the synthesis of polysubstituted pyrrole derivatives via intermolecular cycloaddition of substituted 1-phenyl-2-(phenylamino)-ethan-1-one/1-phenyl-2-(phenylamino)-propan-1-ones/2-((4-methoxyphenyl)amino)-1-(thiophen-2-yl)ethan-1-one/1-(furan-2-yl)-2-((4-methoxyphenyl)amino)ethan-1-one/1-(benzofuran-3-yl)-2-((4-methoxyphenyl)amino)ethan-1-one and dialkyl acetylene dicarboxylate/ethylbutynoate in the presence of a combination of sodium dodecyl sulphate (SDS) and Triton X-100 surfactants using water as a solvent at room temperature in 2–6 h under microwave conditions (10 min) with good to excellent yields.

Diethyl-1-(4-methoxyphenyl)-4-(p-tolyl)-1H-pyrrole 2,3dicarboxylate

STR1

white solid, yield 77%, mp 128-130 ;

1H NMR (400 MHz, CDCl3) δ 7.38(d, J = 8.2,2H), 7.31 (d, J = 7.9, 2H), 7.21 (d, J = 7.12, 2H), 6.99-6.96 (m, 3H), 4.31 (q, J = 7.2 Hz, 2H), 4.12 (q, J = 7.6Hz, 2H), 3.88 (s, 3H), 2.38 (s, 3H), 1.31 (t, J = 7.9Hz, 3H), 1.19 (t, J = 7.5Hz, 3H) ;

13C NMR (100 MHz, CDCl3) δ 166.3, 159.9, 149.0, 148.8, 136.7, 132.6, 130.3, 129.2, 127.6, 125.8, 124.5, 123.4, 121.5, 118.3, 110.5, 110.2, 61.2, 60.7, 56.0, 21.1, 14.0, 13.9.

IR (KBr) ṽ (cm-1): 2981.9, 1717.9, 1514.1, 1419.2, 1381.3, 1245.0, 1175.9, 1226.7, 1043.6, 835.7, 755.3, 663.

HRESIMS: m/zcalcd for [M+H]+ C24H26NO5 408.1805 found 408.1845.

STR1 STR2

 

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O=C(OCC)c2c(c(cn2c1ccc(OC)cc1)c3ccc(C)cc3)C(=O)OCC

“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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An efficient green protocol for the synthesis of tetra-substituted imidazoles catalyzed by zeolite BEA: effect of surface acidity and polarity of zeolite

 spectroscopy, SYNTHESIS, Uncategorized  Comments Off on An efficient green protocol for the synthesis of tetra-substituted imidazoles catalyzed by zeolite BEA: effect of surface acidity and polarity of zeolite
Nov 032017
 

Image result for Kalpana C. Maheria sv

1-benzyl-2, 4, 5-triphenyl-1H-imidazole

STR1 STR2 str3

. 1-Benzyl-2,4,5-triphenyl-1H-imidazole (5a, n = 1).

Off-white solid; m.p.: 160–162 °C;

anal. calcd. for C28H22N2: C, 87.01, H, 5.74, N, 7.25%. Found: C, 87.13, H, 5.70, N, 7.19%;

UV (λmax, ethanol) = 280 nm;

FT-IR (KBr, cm−1 ): 3060 (C–H stretch), 3031, 1600 (CN), 1497, 1483, 1447 (CC), 1352 (C–N stretch), 769, 697 (C–H band);

1 H NMR (400 MHz, DMSO): 5.16 (s, 2H, CH2), 6.74–7.67 (m, 20H, Ar–H) ppm;

13C NMR (100 MHz, DMSO): 47.6 (CH2, C8), 125.1 (CHarom, C28), 126.0 (CHarom, C26), 126.2 (CHarom, C30), 126.4 (CHarom, C11), 127.0 (CHarom, C15), 127.1 (CHarom, C16), 127.7 (CHarom, C20), 128.0 (CHarom, C21), 128.1 (CHarom, C25), 128.4 (CHarom, C13), 128.5 (CHarom, C18), 128.6 (CHarom, C27), 128.8 (C1), 128.8 (CHarom, C12), 128.9 (CHarom, C14), 130.1 (CHarom, C17), 130.3 (CHarom, C19), 130.5 (CHarom, C22), 130.7 (CHarom, C24), 131.0 (CHarom, C29), 134.4 (CHarom, C9), 135.1 (CHarom, C23), 136.8 (CHarom, C7), 137.0 (CHarom, C10), 137.2 (CHarom, C6), 145.4 (C2), 147.0 (C4) ppm;

MS: m/z = 387.5 (M + H)+

An efficient green protocol for the synthesis of tetra-substituted imidazoles catalyzed by zeolite BEA: effect of surface acidity and polarity of zeolite

*Corresponding authors

Abstract

In the present study, the catalytic activity of various medium (H-ZSM-5) and large pore (H-BEA, H-Y, H-MOR) zeolites were studied as solid acid catalysts. The zeolite H-BEA is found to be an efficient catalyst for the synthesis of 1-benzyl-2,4,5-triphenyl-1H-imidazoles through one-pot, 4-component reaction (4-CR) between benzil, NH4OAc, substituted aromatic aldehydes and benzyl amine. The hydrophobicity, Si/Al ratio and acidic properties of zeolite BEA were well improved by controlled dealumination. The synthesized materials were characterized by various characterization techniques such as XRD, ICP-OES, BET, NH3-TPD, FT-IR, pyridine FT-IR, 27Al and 1H MAS NMR. It has been observed that the dealumination of the parent zeolite H-BEA (12) results in the enhanced strength of Brønsted acidity up to a certain Si/Al ratio which is attributed to the inductive effect of Lewis acidic EFAl species, leading to the higher activity of the zeolite BEA (15) catalyst towards the synthesis of 1-benzyl-2,4,5-triphenyl-1H-imidazoles under thermal solvent-free conditions with good to excellent yields. Using the present catalytic synthetic protocol, diverse tetra-substituted imidazoles, which are among the significant biologically active scaffolds, were synthesized in high yield within a shorter reaction time. The effect of polarity, surface acidity and extra framework Al species of the catalysts has been well demonstrated by means of pyridine FT-IR, and 27Al and 1H MAS NMR. The solvent-free synthetic protocol makes the process environmentally benign and economically viable.

Graphical abstract: An efficient green protocol for the synthesis of tetra-substituted imidazoles catalyzed by zeolite BEA: effect of surface acidity and polarity of zeolite
STR1
STR1
Image result for S. V. National Institute of Technology, Ichchhanath, Surat
Image result for S. V. National Institute of Technology, Ichchhanath, Surat
Image result for S. V. National Institute of Technology, Ichchhanath, Surat
S. V. National Institute of Technology, Ichchhanath, Surat
Image result for Mandvi Science College, Mandvi – 394160, Surat, India
Image result for Mandvi Science College, Mandvi – 394160, Surat, India
Mandvi Science College, Mandvi – 394160, Surat, India

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“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent
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