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

spectroscopy, SYNTHESIS Comments Off

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

Domenico C. M. Albanese,^a Nicoletta Gaggero*^b and Meng Fei^b

*Corresponding authors

^aDepartment of Chemistry, Università degli Studi di Milano, via C. Golgi 19, Milano, Italy

^bDepartment of Pharmaceutical Sciences, Università degli Studi di Milano, via L. Mangiagalli 25, Milano, Italy
E-mail:nicoletta.gaggero@unimi.it

Domenico C. M. Albanese

University of Milan

LocationMilano, Italy

DepartmentDepartment of Chemistry

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

Nicoletta 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

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

SYNTHESIS Comments Off

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

Fergal Byrne,^a Bart Forier,^b Greet Bossaert,^b Charly Hoebers,^b Thomas J. Farmer,^a James H. Clark^a and Andrew J. Hunt*^a

*Corresponding authors

^aGreen Chemistry Centre of Excellence, University of York, York YO10 5DD, UK
E-mail: andrew.hunt@york.ac.uk

^bNitto Belgium, NV Eikelaarstraat 22, Belgium

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.

[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+ ]

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

The University of York , York · Green Chemistry Centre of Excellence

Catalysis, Environmental Chemistry, Green Chemistry

PhD.

The University of York

Green Chemistry Centre of Excellence

York, England, United Kingdom

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NMR predict

[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;

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

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.