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Generation and reactivity of 3-carbethoxy-5-phenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olate

✍ Scribed by Teresa M. V. D. Pinho e Melo; Clara S. B. Gomes; Maria I. L. Soares; Antóanio M. d'A Rocha Gonsalves; José A. Paixão; Ana M. Beja; Manuela Ramos Silva

Publisher
Journal of Heterocyclic Chemistry
Year
2004
Tongue
English
Weight
167 KB
Volume
41
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

3‐Carbethoxy‐5‐phenyl‐5__H__,7__H__‐thiazolo[3,4‐c]oxazol‐4‐ium‐1‐olate was generated from (2__R__,4__R__)‐N‐ethoxyoxalyl‐2‐phenylthiazolidine‐4‐carboxylic acid and its reactivity studied. This münchnone showed low reactivity as dipole although from the reaction with dimethyl acetylenedicarboxylate the corresponding (3__R__)‐3‐phenyl‐17__H__,3__H__‐pyrrolo[1,2‐c]thiazole‐5,6,7‐tricarboxylate could be isolated. The thermolysis of (2__R__,4__R__)‐N‐ethoxyoxalyl‐2‐phenylthiazolidine‐4‐carboxylic acid in refluxing acetic anhydride led to the synthesis of N‐(1‐ethoxycarbonyl‐2‐phenylvinyl)‐2‐phenyl‐4‐thioxo‐1,3‐thiazolidine. The structure of methyl (2__R__,4__R__)‐N‐ethoxyoxalyl‐2‐phenylthiazoliddine‐4‐carboxylate was determined by X‐ray crystallography.

📜 SIMILAR VOLUMES

Syntheses of 7-phenyl-5h-thiazolo[5,4-e]
Syntheses of 7-phenyl-5h-thiazolo[5,4-e]pyrrolo[1,2-a][1,4]diazepin-10(9h)one,7-phenyl-5h-thiazolo[5,4-e][1,2,3,4]tetrazolo[5,1-c]-pyrrolo[1,2-a][1,4]diazepine and 7-phenyl-5h-thiazolo[5,4-e]-[1,3,4] triazolo [5,1-c]pyrrolo [1,2-a] [1,4] diazepines
✍ A. Shafiee; M. Shekarchi 📂 Article 📅 2002 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 48 KB 👁 1 views

## Abstract Fused tricyclic 7‐phenyl‐5__H__‐thizolo[5,4‐__e__]pyrrolo[1,2‐__a__][1,4]diazepin‐10(9__H__)one (**10**) was prepared by thermolysis of 2‐phenyl‐4‐(1‐pyrrolylmethyl)thiazole‐5‐carbonyl azide (**9**) in acetic acid. In addition, starting from **10**, 7‐phenyl‐5__H__‐thiazolo [5,4‐__e__][