Synthesis of (4S*,5S*)-Diphenyl-1,3,4,5-Tetrahydro-2H-[1]Benzopyrano [4,3-d]Pyrimidine-2-Thiones by Base-Catalysed Cyclocondensation of (E)-3-Benzylideneflavanones with Thiourea, and Determination of Their Monoacetylation Site-Reference-Cited by-同舟云学术

Synthesis of (4S*,5S*)-Diphenyl-1,3,4,5-Tetrahydro-2H-[1]Benzopyrano [4,3-d]Pyrimidine-2-Thiones by Base-Catalysed Cyclocondensation of (E)-3-Benzylideneflavanones with Thiourea, and Determination of Their Monoacetylation Site

Published:2004-03 Issue:3 Volume:2004 Page:180-182
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Mallik Asok K.¹,Chattopadhyay Falguni¹,Dey Dilip Kumar¹²,Patra Amarendra³,Elmali Ayhan⁴

Affiliation:

1. Department of Chemistry, Jadavpur University, Kolkata – 700 032, India

2. Present address: Department of Chemistry, Chandidas Mahavidyalaya, Khujutipara 731215, District-Birbhum, West Bengal, India

3. Department of Chemistry, University College of Science, Calcutta University, Kolkata 700 009, India

4. Department of Engineering Physics, Faculty of Engineering, University of Ankara, 06100-Baselver, Ankara, Turkey

Abstract

Base-catalysed cyclocondensation of ( E)-3-benzylideneflavanones with thiourea has been found to be highly stereoselective, producing (4 S*,5 S*)-diphenyl-1,3,4,5-tetrahydro-2 H-[1]benzopyrano[4,3- d]pyrimidine-2-thiones in high yield, the structure of one of which has been determined by X-ray crystallography. Just like 4,6-diaryl-3, 4-dihydropyrimidine-2(1 H)-thiones, the said products also undergo monoacetylation on treatment with Ac2O. The site of acetylation in both of these classes of compound are established by detailed NMR spectral studies.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/0308234041640681

Reference16 articles.

1. Synthesis and spectroscopic studies of the pyrimidine-2(1H)thione derivatives

2. A facile transformation of -3-benzylideneflavanones to 3-(α-hydroxybenzyl) flavones

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