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Cationic and mesoionic 1,3‐thiazolo‐(3,2‐c)quinazoline derivatives

Cationic and mesoionic 1,3‐thiazolo‐(3,2‐c)quinazoline derivatives 4‐Allylthio‐2‐arylquinazolines 4a–c undergo cyclization by action of bromine to furnish 5‐aryl‐3‐bromomethyl‐2,3‐dihydrothiazolo(3,2‐c)quinazolin‐4‐ium bromides 5a–c. Compounds 5a–c undergo ring opening by action of water under acid catalysis to afford the corresponding dibromide derivatives 6a–c. Bromination of 3‐allyl‐2‐aryl‐4(3H)quinazolinethiones 7a–c leads to 5‐aryl‐2‐bromomethyl‐2,3‐dihydrothiazolo(3,2‐c)quinazolin‐4‐ium bromides 8a–c. However, anhydro‐3‐hydroxy‐5‐aryl‐1,3‐thiazolo(3,2‐c)quinazolin‐4‐ium hydroxide 10a–c were prepared by the cyclodehydration of the corresponding thioglycolic acids 9a–c with Ac2O. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:576–580, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10148 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Cationic and mesoionic 1,3‐thiazolo‐(3,2‐c)quinazoline derivatives

Heteroatom Chemistry , Volume 14 (7) – Jan 1, 2003

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References (11)

Publisher
Wiley
Copyright
Copyright © 2003 Wiley Periodicals, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.10148
Publisher site
See Article on Publisher Site

Abstract

4‐Allylthio‐2‐arylquinazolines 4a–c undergo cyclization by action of bromine to furnish 5‐aryl‐3‐bromomethyl‐2,3‐dihydrothiazolo(3,2‐c)quinazolin‐4‐ium bromides 5a–c. Compounds 5a–c undergo ring opening by action of water under acid catalysis to afford the corresponding dibromide derivatives 6a–c. Bromination of 3‐allyl‐2‐aryl‐4(3H)quinazolinethiones 7a–c leads to 5‐aryl‐2‐bromomethyl‐2,3‐dihydrothiazolo(3,2‐c)quinazolin‐4‐ium bromides 8a–c. However, anhydro‐3‐hydroxy‐5‐aryl‐1,3‐thiazolo(3,2‐c)quinazolin‐4‐ium hydroxide 10a–c were prepared by the cyclodehydration of the corresponding thioglycolic acids 9a–c with Ac2O. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:576–580, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10148

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 2003

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