Cationic and mesoionic 1,3-thiazolo-[3,2-c]quinazoline derivatives
✍ Scribed by A. A. F. Wasfy
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- English
- Weight
- 80 KB
- Volume
- 14
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.10148
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✦ Synopsis
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 Ac~2~O. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:576–580, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10148
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