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DR ANTHONY MELVIN CRASTO, WORLDDRUGTRACKER

2,2,5,5-Tetramethyltetrahydrofuran (TMTHF): a non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents

 SYNTHESIS  Comments Off on 2,2,5,5-Tetramethyltetrahydrofuran (TMTHF): a non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents
Jul 132017
 

 

2,2,5,5-Tetramethyltetrahydrofuran (TMTHF): a non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC01392B, Paper
Fergal Byrne, Bart Forier, Greet Bossaert, Charly Hoebers, Thomas J. Farmer, James H. Clark, Andrew J. Hunt
An inherently non-peroxide forming ether solvent, 2,2,5,5-tetramethyltetrahydrofuran (2,2,5,5-tetramethyloxolane), has been synthesized from readily available and potentially renewable feedstocks, and its solvation properties have been tested

2,2,5,5-Tetramethyltetrahydrofuran (TMTHF): a non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents

 

http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC01392B?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Abstract

An inherently non-peroxide forming ether solvent, 2,2,5,5-tetramethyltetrahydrofuran (2,2,5,5-tetramethyloxolane), has been synthesized from readily available and potentially renewable feedstocks, and its solvation properties have been tested. Unlike traditional ethers, its absence of a proton at the alpha-position to the oxygen of the ether eliminates the potential to form hazardous peroxides. Additionally, this unusual structure leads to lower basicity compared with many traditional ethers, due to the concealment of the ethereal oxygen by four bulky methyl groups at the alpha-position. As such, this molecule exhibits similar solvent properties to common hydrocarbon solvents, particularly toluene. Its solvent properties have been proved by testing its performance in Fischer esterification, amidation and Grignard reactions. TMTHF’s differences from traditional ethers is further demonstrated by its ability to produce high molecular weight radical-initiated polymers for use as pressure-sensitive adhesives.

STR1

[TMTHF].

1H NMR (400 MHz, CDCl3): δ 1.81 (s, 4H), 1.21 (s, 12H);

13C NMR (400 MHz, CDCl3): δ 29.75, 38.75, 80.75;

IR 2968, 2930, 2968, 1458, 1377, 1366, 1310, 1265, 1205, 1144, 991, 984, 885, 849, 767 cm−1;

m/z (%): (ESI–MS) 128 (40) [M+ ]

STR1

 

Fergal Byrne

Fergal Byrne

PHD Researcher at Green Chemistry Centre of Excellence

University of York

York, United Kingdom

University of York

Green Chemistry Centre of Excellence, University of York, York YO10 5DD, UK 

 

Andrew Hunt

Andrew Hunt

Catalysis, Environmental Chemistry, Green Chemistry

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NMR predict

[TMTHF].

1H NMR (400 MHz, CDCl3): δ 1.81 (s, 4H), 1.21 (s, 12H);

STR1 STR2

13C NMR (400 MHz, CDCl3): δ 29.75, 38.75, 80.75;

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Synthesis, Biological Evaluation and Validation Studies of Novel 5-(Substituted Aldehyde)-2-imino-7-methyl-3-oxo-N-phenyl-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxamide Scaffolds

 Uncategorized  Comments Off on Synthesis, Biological Evaluation and Validation Studies of Novel 5-(Substituted Aldehyde)-2-imino-7-methyl-3-oxo-N-phenyl-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxamide Scaffolds
Jun 072016
 

synthesis

Procedure for the synthesized derivatives (1-3)

Step 1: The synthesis of Intermediate-1 (2-imino-6-methyl-4- (substituted aldehyde)-N-phenyl-1,2,3,4-tetrahydropyrimidine-5- carboxamide): A mixture of substituted aldehyde (0.01 mol), guanidine nitrate (0.015 mol) and acetoacetanilide (0.01 mol) were placed in round bottom flask in methanol (50 ml) and added aluminum chloride (0.003 mol) with 2-3 drops of conc. hydrochloric acid as catalyst amount then the reaction mixture was refluxed for 11-12 hrs after that the reaction mixture was cooled to room temperature and poured into crushed ice water with vigorous stirring, filtered and recrystallized with methanol [10].

Step 2: The synthesis of 5-(substituted aldehyde)-7-methyl-3-oxo-N-phenyl-2-((3,4,5,6-tetrahydroxy-tetrahydro-2H-pyran- 2-yl)methylene)-1,2,3,5-tetrahydroimidazo[1,2-a] pyrimidine-6- carboxamide derivatives: A mixture of intermediate-1 (0.01 mol), sodium benzoate (2 g), dextrose (0.01 mol), glacial acetic acid (20 ml), ethyl acetoacetate (15 ml) and monochloroacetic acid (0.015 mol) were taken in RBF and refluxed with controlled temperature at 140-142°C for 6-7 hrs. The reaction mixture was cooled at room temperature and poured into ice cold water to yielded solid precipitate or titled compounds (1-3), filtered and recrystallized with methanol.

Compound 1 (7-Methyl-3-oxo-N-phenyl-2-((3,4,5,6- tetrahydroxy-tetrahydro-2H-pyran-2-yl)methylene)-5-(3,4,5- trimethoxyphenyl)-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6- carboxamide): IR (KBr pellets, cm-1): 3062 (C-H str., phenyl nucleus), 1596 (C=C str., phenyl nucleus), 694 (C-C str., phenyl nucleus), 1630 (C=O str.,), 3321 (N-H str., 2˚amide), 1630 (N=CH str., pyrimidine), 1244 (C-N str., pyrimidine), 2779 (C-H str., cyclic ether), 1126 (C-O-C str., aryl ether), 3321 (O-H str., polyhydroxy on dextrose), 1244 (C-O-C str., OCH3); 1H NMR (DMSO-d6, δppm): 7.45-7.49 (m, 7H, Ar-H), 2.10 (s, 1H, NH, amide), 8.25 (s, 1H, NH, amide), 3.86-4.22 (m, 5H, CH, tetrahydropyran), 2.10 (m, 4H, OH alcohol), 3.86 (m, 9H, OCH3).

Synthesis, Biological Evaluation and Validation Studies of Novel 5-(Substituted Aldehyde)-2-imino-7-methyl-3-oxo-N-phenyl-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxamide Scaffolds

Jyoti Rani, Monika Saini, Sanjiv Kumar and Prabhakar Kumar Verma*
Department of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak-124 001, Haryana, India
*Corresponding Author : Prabhakar Kumar Verma
Department of Pharmaceutical Sciences
Maharshi Dayanand University
Rohtak-124 001, Harayana, India
Tel: 9992581437
E-mail: vermapk422@rediffmail.com
Received March 07, 2016; Accepted March 29, 2016; Published March 31, 2016
Citation: Rani J, Saini M, Kumar S, Verma PK (2016) Synthesis, Biological Evaluation and Validation Studies of Novel 5-(Substituted Aldehyde)-2-imino-7-methyl-3-oxo-N-phenyl-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxamide Scaffolds. Med chem (Los Angeles) 6:218-223. doi:10.4172/2161-0444.1000349
Copyright: © 2016 Rani J, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

 

link

http://www.omicsonline.org/open-access/synthesis-biological-evaluation-and-validation-studies-of-novel-5substituted-aldehyde2imino7methyl3oxonphenyl1235tetrahydroimidazo-2161-0444-1000349.php?aid=71794

///////////// 5-(Substituted Aldehyde)-2-imino-7-methyl-3-oxo-N-phenyl-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxamide,  Scaffolds

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