AUTHOR OF THIS BLOG

DR ANTHONY MELVIN CRASTO, WORLDDRUGTRACKER
Feb 082018
 

Med. Chem. Commun., 2018, Advance Article
DOI: 10.1039/C7MD00551B, Research Article
Yi-Bin Li, Wen Hou, Hui Lin, Ping-Hua Sun, Jing Lin, Wei-Min Chen
Two series of 5-hydroxy-2-methyl-4H-pyran-4-one derivatives were synthesized and their antiglioma activities were evaluated.

Design, synthesis and biological evaluation of novel 5-hydroxy-2-methyl-4H-pyran-4-one derivatives as antiglioma agents

Author affiliations

Abstract

D-2-Hydroxyglutarate (D-2HG) is frequently found in human brain cancers. Approximately 50–80% of grade II glioma patients have a high level of D-2HG production, which can lead to cancer initiation. In this study, a series of novel 5-hydroxy-2-methyl-4H-pyran-4-one derivatives were designed and synthesized as antiglioma agents, and their related structure–activity relationships are discussed. Among these novel compounds, 4a exhibited promising anti-proliferative activity against glioma HT1080 cells and U87 cells with an IC50 of 1.43 μM and 4.6 μM, respectively. Further studies found that the most active compound (4a) shows an 86.3% inhibitory rate against the intracellular production of D-2HG at 1 μM, and dramatic inhibitory effects, even at 1 μM on the colony formation and migration of U87 and HT1080 cells.

STR1 STR2 str3 str4
6,6′-((4-(Benzyloxy)phenyl)methylene)bis(5-hydroxy-2-methyl-4H-pyran-4- one) (4a) The reaction was performed according to the general procedure C, using 1 (1.00 g, 7.90 mmol) and 4-(benzyloxy)benzaldehyde (0.84 g, 3.95 mmol).2 The crude product was recrystallized from isopropanol affording a white powder 4a (1.53 g, 87%): mp 261.4-262.1oC; 1HNMR (300 MHz, DMSO-d6)  2.22 (s, 6H, CH3), 5.08 (s, 3H, OCH2- Ph), 5.96 (s, 1H, CH-Ar), 6.25 (s, 2H, C=CH), , 7.01 (d, J = 9.0 Hz, 2H, Ar-H3’/H5’), 7.22 (d, J = 9.0 Hz, 2H, Ar-H2’/H6’), 7.31-7.45 (m, 5H, Ph-H); 13CNMR (75 MHz, DMSO-d6)  173.95, 165.08, 158.12, 151.20, 147.68, 142.19, 140.77, 137.42, 129.87, 128.91, 128.16, 127.69, 115.46, 114.97, 111.74, 69.69, 19.63; ESI-MS m/z: 447.1 [M+H]+ ; ESI-HRMS m/z: 447.1438 [M+H]+ , calcd for C26H23O7 447.1438.
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Feb 082018
 

Abstract Image

Unconventional Method for Synthesis of 3-Carboxyethyl-4-formyl(hydroxy)-5-aryl-N-arylpyrazoles

 Departamento de Química, Universidade Estadual de Maringá (UEM), 87030-900 Maringá, PR, Brazil
 Departamento de Química, Universidade Federal de Santa Maria (UFSM), 97110-970 Santa Maria, RS, Brazil
§ Instituto de Biotecnologia, Universidade de Caxias do Sul (UCS), 295070-560 Caxias do Sul, RS, Brazil
J. Org. Chem.201782 (23), pp 12590–12602
DOI: 10.1021/acs.joc.7b02361
Publication Date (Web): November 2, 2017
*E-mail: farosa@uem.br

Abstract

An alternative highly regioselective synthetic method for the preparation of 3,5-disubstituted 4-formyl-N-arylpyrazoles in a one-pot procedure is reported. The methodology developed was based on the regiochemical control of the cyclocondensation reaction of β-enamino diketones with arylhydrazines.

Structural modifications in the β-enamino diketone system allied to the Lewis acid carbonyl activator BF3 were strategically employed for this control. Also a one-pot method for the preparation of 3,5-disubstituted 4-hydroxymethyl-N-arylpyrazole derivatives from the β-enamino diketone and arylhydrazine substrates is described.

J. Org. Chem. 20178212590

4-Formyl-N-arylpyrazole substrates occupy a prominent position in the field of organic synthesis since they are key intermediates in obtaining a wide range of biologically active compounds. Because of the synthetic versatility of the 4-formyl-N-arylpyrazole skeleton, their synthesis has been extensively explored. In an extension of their previously published research,
Rosa and co-workers at Universidade Estadual de Maringá described a one-pot synthetic method that regioselectively produced 3,5-disubstituted-4-formyl-N-arylpyrazoles . The β-enamino diketone starting materials were readily synthesized via published procedures. High regioselectivity was secured via the use of BF3·OEt2 as the carbonyl activator and a bulky amine as the enamine component. Acetonitrile proved to be the most suitable solvent for the reaction.
After an aqueous workup, the desired pyrazoles were obtained in excellent yields. A variety of functional groups were tolerated on the two aryl substituents. This operationally simple procedure afforded the 4-formyl-N-arylpyrazoles in high yields, regioselectively. Furthermore, the formyl group could be reduced in situ with sodium borohydride to generate the corresponding 4-hydroxymethyl-N-arylpyrazoles.
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3-(Ethoxycarbonyl)-4-formyl-5-(4-nitrophenyl)-1-phenyl-1H-pyrazole (3a)

Light yellow solid; yield: 0.150 g (82%); mp 147.0–149.2 °C;
1H NMR (300.06 MHz, CDCl3) δ (ppm) 1.47 (t, 3H, J = 7.1 Hz, O–CH2–CH3), 4.54 (q, 2H, J = 7.1 Hz, O–CH2-CH3), 7.19–7.25 (m, 2H, Ph), 7.32–7.43 (m, 3H, Ph), 7.48 (d, 2H, J = 8.9 Hz, 4-NO2C6H4), 8.19 (d, 2H, J = 8.9 Hz, 4-NO2C6H4), 10.57 (s, 1H, CHO);
13C NMR (75.46 MHz, CDCl3) δ (ppm) 14.4 (O–CH2CH3), 62.3 (O-CH2–CH3), 122.0 (C4), 123.5 (4-NO2C6H4), 125.9 (Ph), 129.5 (Ph), 129.6 (Ph), 131.8 (4-NO2C6H4), 134.1 (4-NO2C6H4), 137.8 (Ph), 143.5 (C5), 145.0 (C3), 148.4 (4-NO2C6H4), 161.5 (COOEt), 186.6 (CHO);
HRMS (ESI+): calcd for C19H16N3O5+, [M+H]+: 366.1084, found 366.1101.
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Feb 082018
 

 

Green Chem., 2018, Advance Article
DOI: 10.1039/C7GC03619A, Communication
Yahui Li, Zechao Wang, Xiao-Feng Wu
A sustainable procedure for the synthesis of various alkyl arylacetates from benzyl alcohols has been developed

A sustainable procedure toward alkyl arylacetates: palladium-catalysed direct carbonylation of benzyl alcohols in organic carbonates

Author affiliations

Abstract

A sustainable procedure for the synthesis of various alkyl arylacetates from benzyl alcohols has been developed. With palladium as the catalyst and organic carbonates as the green solvent and in situ activator, benzyl alcohols were carbonylated in an efficient manner without any halogen additives.

Ethyl 2-phenylacetate

1H NMR (300 MHz, Chloroform-d) δ 7.32 – 7.08 (m, 5H), 4.08 (q, J = 7.1 Hz, 2H), 3.54 (s, 2H), 1.18 (t, J = 7.1 Hz, 3H).

13C NMR (75 MHz, CDCl3) δ 171.61, 134.17, 129.24, 128.54, 127.03, 60.85, 41.45, 14.18.

 

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Bio-derived production of cinnamyl alcohol via a three step biocatalytic cascade and metabolic engineering

 PROCESS, spectroscopy, SYNTHESIS, Uncategorized  Comments Off on Bio-derived production of cinnamyl alcohol via a three step biocatalytic cascade and metabolic engineering
Jan 122018
 

Green Chem., 2018, Advance Article
DOI: 10.1039/C7GC03325G, Paper
Evaldas Klumbys, Ziga Zebec, Nicholas J. Weise, Nicholas J. Turner, Nigel S. Scrutton
Cascade biocatalysis and metabolic engineering provide routes to cinnamyl alcohol.

Bio-derived production of cinnamyl alcohol via a three step biocatalytic cascade and metabolic engineering

* Corresponding authors

Prof Nigel ScruttonScD, FRSC, FRSB

Professor of Enzymology and Biophysical Chemistry

Abstract

The construction of biocatalytic cascades for the production of chemical precursors is fast becoming one of the most efficient approaches to multi-step synthesis in modern chemistry. However, despite the use of low solvent systems and renewably resourced catalysts in reported examples, many cascades are still dependent on petrochemical starting materials, which as of yet cannot be accessed in a sustainable fashion. Herein, we report the production of the versatile chemical building block cinnamyl alcohol from the primary metabolite and the fermentation product L-phenylalanine. Through the combination of three biocatalyst classes (phenylalanine ammonia lyase, carboxylic acid reductase and alcohol dehydrogenase) the target compound could be obtained in high purity, demonstrable at the 100 mg scale and achieving 53% yield using ambient temperature and pressure in an aqueous solution. This system represents a synthetic strategy in which all components present at time zero are biogenic and thus minimises damage to the environment. Furthermore we extend this biocatalytic cascade by its inclusion in an L-phenylalanine overproducing strain of Escherichia coli. This metabolically engineered strain produces cinnamyl alcohol in mineral media using glycerol and glucose as the carbon sources. This study demonstrates the potential to establish green routes to the synthesis of cinnamyl alcohol from a waste stream such as glycerol derived, for example, from lipase treated biodiesel.

(R)-3-amino-3-(3-fluorophenyl)propanoic acid (1c) 1H NMR (CDCl3): δ 7.16-7.31 (m, 5H, ArH), 6.50-6.54 (d, 1H, J = 16 Hz, C=CH), 6.23-6.30 (dt, 1H, J = 16, 8 Hz, C=CHCH2 ), 4.21-4.23 (dd, 2H, J = 8, 4 Hz, C=CHCH2); 13C NMR (CDCl3): 136.70, 131.09, 128.60, 128.54, 127.69, 126.48, 63.65.

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////////////cinnamyl alcohol,  biocatalytic, metabolic engineering

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Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides

 organic chemistry, spectroscopy, SYNTHESIS  Comments Off on Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides
Dec 292017
 

 

Green Chem., 2018, Advance Article
DOI: 10.1039/C7GC02627G, Paper
Kathiravan Murugesan, Thirusangumurugan Senthamarai, Manzar Sohail, Muhammad Sharif, Narayana V. Kalevaru, Rajenahally V. Jagadeesh
Nanoscale Fe2O3-catalyzed environmentally benign synthesis of nitriles and amides has been performed from easily accessible aldehydes and ammonia using O2.

Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides

Author affiliations

Abstract

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.

1H NMR (300 MHz, Chloroform-d) δ 7.17 – 6.96 (m, 2H), 6.93 – 6.70 (m, 1H), 4.33 – 4.11 (m, 4H). 13C NMR (75 MHz, Chloroform-d) δ 147.75 , 143.80 , 125.87 , 121.21 , 118.91 , 118.25 , 104.38 , 64.59 , 64.12 . Off white solid

STR1 STR2 str3

STR1

cas 19102-07-9

  • 1,4-Benzodioxan-6-carbonitrile (8CI)
  • 2,3-Dihydro-1,4-benzodioxin-6-carbonitrile
  • 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)nitrile

 

MP

Melting Point, °C
105 – 106

Tetrahedron, 2015, vol. 71,  29, p. 4883 – 4887

NMR PREDICTS

1H NMR

 

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13C NMR PREDICT

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More…………….

Journal of the American Chemical Society, 2001, vol. 123, 49, p. 12202 – 12206

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More………….

RSC Advances, 2013, vol. 3, 44, p. 22389 – 22396

http://www.rsc.org/suppdata/ra/c3/c3ra44386h/c3ra44386h.pdf

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MORE……..

Organic Letters, 2017, vol. 19,  12, p. 3095 – 3098

http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.7b01199/suppl_file/ol7b01199_si_001.pdf

2,3-Dihydrobenzo[b][1,4]dioxine-6-carbonitrile (Scheme 1, 2n) According to the general procedure A, the reaction of 1n (0.20 mmol), zinc cyanide (2.0 equiv), PCyPh2 (0.20 equiv) and Pd(OAc)2 (0.05 equiv) in dioxane (0.25 M) for 16 h at 150 °C, afforded after work-up and chromatography the title compound in 75% yield (24.2 mg). White solid. 1H NMR (500 MHz, CDCl3) δ 7.17-7.11 (m, 2H), 6.91 (d, J = 8.1 Hz, 1H), 4.32-4.31 (m, 2H), 4.30- 4.26 (m, 2H). 13C NMR (125 MHz, CDCl3) δ 147.84, 143.91, 126.04, 121.37, 119.01, 118.37, 104.62, 64.71, 64.24.

STR1 STR2

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Sulfurative self-condensation of ketones and elemental sulfur: a three-component access to thiophenes catalyzed by aniline acid-base conjugate pairs

 green chemistry, organic chemistry, PROCESS, spectroscopy, SYNTHESIS  Comments Off on Sulfurative self-condensation of ketones and elemental sulfur: a three-component access to thiophenes catalyzed by aniline acid-base conjugate pairs
Dec 282017
 

 

Green Chem., 2018, Advance Article
DOI: 10.1039/C7GC03437G, Communication
Thanh Binh Nguyen, Pascal Retailleau
An aniline/acid-catalyzed method for constructing thiophenes 2 from inexpensive ketones 1 and elemental sulfur is reported.

Sulfurative self-condensation of ketones and elemental sulfur: a three-component access to thiophenes catalyzed by aniline acid–base conjugate pairs

Author affiliations

Abstract

A sulfurative self-condensation method for constructing thiophenes 2 by a reaction between ketones 1 and elemental sulfur is reported. This reaction, which is catalyzed by anilines and their salts with strong acids, starts from readily available and inexpensive materials, and releases only water as a by-product.

STR1

 

2,4-Di-p-tolylthiophene (2b)2

2 M. Arisawa, T. Ichikawa, and M. Yamaguchi, Chem. Commun. 2015, 51, 8821

STR1

Eluent heptane:toluene 9:1. 190 mg, 72%.

1 H NMR (300 MHz, CDCl3) δ 7.60-7.54 (m, 5H), 7.34 (s, 1H), 7.27-7.23 (m, 4H), 2.42 (s, 6H).

13C NMR (75 MHz, CDCl3) δ 145.3, 143.3, 137.8, 137.2, 133.5, 131.9, 129.9, 129.8, 126.5, 126.0, 122.1, 118.9, 21.5, 21.5.

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STR1

Binh Thanh Nguyen at French National Centre for Scientific Research

Binh Thanh Nguyen

CV Binh Nguyen

CNRS Research Associate CR1 ( ORCID , ResearchGate )

ICSN-CNRS Bât. 27

1, avenue de la Terrasse

91190 Gif-sur-Yvette France

thanh-binh.nguyen_at_cnrs.fr

+33 1 69 82 45 49

- Education and work experience2015: Habilitation to Direct Research (HDR)

2011 – present: CNRS research associate at ICSN – Paris-Saclay University

2009 – 2011: Post-doctoral Fellow at ICSN (Dr. Françoise Guéritte and Dr. Qian Wang)

2003 – 2006: Ph.D. student at the UCO2M Organic Synthesis Laboratory (University of Maine, Le Mans, France, Dr. Gilles Dujardin, Dr. Arnaud Martel, Professor Robert Dhal)

- Research Interests

Green chemistry (Atom, step and redox economic transformation), green synthetic tools: O2, S8, photochemistry, iron catalyst

Elemental sulfur as a synthetic tool (building block, oxidant, reductant, catalyst)

Iron-sulfur catalysts

Heterocycle synthesis

- Scientific Communications

47 publications

- Selected recent publications ( complete list )

[1] Adv. Synth. Catal. 2017 , 359 , 1106.

[2] Asian J. Org. Chem. 2017 , 6 , 477.

[3] Org. Lett. 2016 , 18 , 2177.

[4] Org. Process Res. Dev. 2016 , 20 , 319.

[5] Angew. Chem. Int. Ed. 2014 , 53 , 13808.

[6] J. Am. Chem. Soc. 2013 , 135 , 118.

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HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction

 organic chemistry, spectroscopy, SYNTHESIS  Comments Off on HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction
Dec 212017
 

Green Chem., 2018, Advance Article
DOI: 10.1039/C7GC03425C, Paper
Weigang Fan, Yves Queneau, Florence Popowycz
The use of the renewable platform molecule 5-hydroxymethylfurfural (HMF) in the multi-component Biginelli reaction has been investigated.

HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction

http://pubs.rsc.org/en/Content/ArticleLanding/2018/GC/C7GC03425C?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Abstract

The use of the renewable platform molecule 5-hydroxymethylfurfural (HMF) in the multi-component Biginelli reaction has been investigated. Multicomponent reactions (MCR) using HMF offer straightforward access to novel fine chemicals. However, the peculiar reactivity and lower stability of HMF have limited its use in such strategies. In this paper, we report our results on the use of HMF in 3-component Biginelli reactions, leading in one single step to a series of functionalized dihydropyrimidinones obtained in moderate to good yields, with a broad substrate scope of 1,3-dicarbonyl compounds and urea building blocks. This is the first report on the use of HMF in this reaction. The CH2OH motif found in HMF provides useful functionalization for the target molecules, which cannot be offered by simpler aldehydes such as furfural.

5-Acetyl-4-[5’-(hydroxymethyl)furan-2’-yl]-6-methyl-3,4-dihydropyrimidin-2(1H)-one (4a):

STR1 STR2

Reaction time: 8 h; Global yield: 86%; (78% yield after simple filtration + additional 8% yield after purification of the filtrate by column chromatography).

1H NMR (400 MHz, DMSO-d6) δ 9.22 (d, 1H, J = 1.2 Hz, H1), 7.88 (dd, 1H, J = 3.4, 1.2 Hz, H3), 6.16 (d, 1H, J = 3.1 Hz, H4’), 6.03 (d, 1H, J = 3.1 Hz, H3’), 5.27 (d, 1H, J = 3.4 Hz, H4), 5.18 (t, 1H, J = 5.6 Hz, OH), 4.33 (d, 2H, J = 5.6 Hz, CH2), 2.25 (s, 3H, CH3-C6), 2.17 (s, 3H, CH3CO).

13C NMR (100 MHz, DMSO-d6) δ 193.9 (COCH3), 155.1, 154.9 (C2’, C5’), 152.4 (C2), 149.0 (C6), 107.7 (C4’), 107.1 (C5), 106.3 (C3’), 55.7 (CH2OH), 47.9 (C4), 30.0 (CH3CO), 19.0 (CH3-C6).

HRMS (ESI) m/z: Calcd for [M+Na]+ C12H14N2NaO4 273.0846; Found 273.0850.

 

Weigang Fan at Institut National des Sciences Appliquées de Lyon

Institut National des Sciences Appliquées de Lyon

Research experience

  • Sep 2015–Mar 2017
    Doctorant
    Institut National des Sciences Appliquées de Lyon · Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires (ICBMS – UMR 5246)
    France · Lyon
Image result for Florence Popowycz lyon
Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie Organique et Bioorganique, UMR 5246 CNRS, Université Lyon 1, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France
E-mail:  florence.popowycz@insa-lyon.fr
Image result for Yves Queneau lyon

Yves QUENEAU

CNRS Research Director chez ICBMS INSA Lyon Univ Lyon – Carbohydrate Chemistry

ICBMS INSA Lyon University of Lyon

Queneau
Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie Organique et Bioorganique, UMR 5246 CNRS, Université Lyon 1, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France
E-mail: yves.queneau@insa-lyon.fr,
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Synthesis of highly functional carbamates through ring-opening of cyclic carbonates with unprotected α-amino acids in water

 organic chemistry, spectroscopy, SYNTHESIS  Comments Off on Synthesis of highly functional carbamates through ring-opening of cyclic carbonates with unprotected α-amino acids in water
Dec 202017
 

Green Chem., 2018, Advance Article
DOI: 10.1039/C7GC02862H, Paper
Peter Olsen, Michael Oschmann, Eric V. Johnston, Bjorn Akermark
Ring opening of cyclic carbonates with unprotected amino acids in water – a route to highly functional carbamates.

Synthesis of highly functional carbamates through ring-opening of cyclic carbonates with unprotected α-amino acids in water

 Author affiliations

Abstract

The present work shows that it is possible to ring-open cyclic carbonates with unprotected amino acids in water. Fine tuning of the reaction parameters made it possible to suppress the degree of hydrolysis in relation to aminolysis. This enabled the synthesis of functionally dense carbamates containing alkenes, carboxylic acids, alcohols and thiols after short reaction times at room temperature. When Glycine was used as the nucleophile in the ring-opening with four different five membered cyclic carbonates, containing a plethora of functional groups, the corresponding carbamates could be obtained in excellent yields (>90%) without the need for any further purification. Furthermore, the orthogonality of the transformation was explored through ring-opening of divinylenecarbonate with unprotected amino acids equipped with nucleophilic side chains, such as serine and cysteine. In these cases the reaction selectively produced the desired carbamate, in 70 and 50% yield respectively. The synthetic design provides an inexpensive and scalable protocol towards highly functionalized building blocks that are envisioned to find applications in both the small and macromolecular arena.

link  http://pubs.rsc.org/en/Content/ArticleLanding/2018/GC/C7GC02862H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

STR1 STR2
Image result for Peter Olsén stockholm
Affiliation

Stockholm University

Location
  • Stockholm, Sweden
Position
  • PostDoc Position

Research experience

  • Jun 2010–Feb 2016
    PhD Student
    KTH Royal Institute of Technology · Department of Fibre and Polymer Technology
    Sweden · Stockholm
Stockholms universitet hem
Image result for Björn Åkermark stockholm

Education

  • Jan 1962–Jun 1967
    KTH Royal Institute of Technology
    Organic Chemistry and Catalysis · PhD
    Sweden · Stockholm

Awards & achievements

  • Jun 2009

    Award: Bror Holmberg Medal, Swedish Chemical Society

  • Feb 2009

    Award: Ulla and Stig Holmquists Prize, Uppsala University

  • Oct 1997

    Award: Dr hc, University D´Aix-Marseille

  • Oct 1991

    Award: KTH Prize for Excellence in Teaching

  • Oct 1978

    Award: Arrhenius Medal, Swedish Chemical Society

  • Aug 1977

    Scholarship: Zorn Fellowship, Swden America Foundation

  • Nov 1976

    Award: Letterstedt Award, Roy Swed. Acad. of Science

6.jpg

Dr. Eric Johnston, Ph.D.

Sigrid Therapeutics

Chief Technology Officer

Dr. Eric V. Johnston obtained his Master of Science degree in 2008 at the Department of Organic Chemistry, Stockholm University, Sweden. In the same year, he started his graduate studies under the supervision of Prof. Jan-Erling Bäckvall. During his PhD, he worked on the development of new homogeneous and heterogeneous transition-metal catalysts.

After receiving his PhD in 2012, he joined Prof. Samuel J. Danishefskys research group at Memorial Sloan-Kettering Cancer Center, New York, USA as a postdoctoral fellow supported by The Swedish Research Council. Here he was engaged in the total chemical synthesis of glycolsylated proteins that play important roles in modern cancer treatment.

In 2014 he returned to the Department of Organic Chemistry at Stockholm University to establish his own group. The goal of his research is to contribute new advances to the strategy and methodology for the preparation of synthetic macromolecules such as proteins, glycopeptides, sequence and length-controlled polymers. He is also a Co-Supervisor for Prof. Björn Åkermarks research group, which aims at studying and developing new homogeneous, as well as heterogeneous, water oxidation catalysts.

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

 spectroscopy, SYNTHESIS  Comments Off on A practical synthesis of 2,3-dihydro-1,5-benzothiazepines
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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Persulfurated Coronene: A New Generation of “Sulflower”

 spectroscopy, SYNTHESIS, Uncategorized  Comments Off on Persulfurated Coronene: A New Generation of “Sulflower”
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
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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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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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