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Synthesis of 4-(2-hydroxyphenyl)-1-phenyl-1,2,4-triazolidine-3,5-dione derivatives through cyclic transformations of 3-(2-phenylcarbazoyl)-2(3H)-benzoxazolone derivatives

✍ Scribed by François Chau; René Milcent

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
170 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Four 3‐(3‐benzylidene‐2‐phenylcarbazoyl)‐2(3__H__)‐benzoxazolone derivatives 3 have been synthesized from benzoxazolone derivatives 1 and benzaldehyde N‐chloroformylphenylhydrazone 2. By acid hydrolysis, these compounds yielded 3‐(2‐phenylcarbazoyl)‐2(3__H__)benzoxazolone derivatives 4 which were not isolated and were transformed via an intramolecular reaction into 4‐(2‐hydroxyphenyl)‐1‐phenyl‐1,2,4‐triazolidine‐3,5‐dione derivatives 5 in a good yield. Attempts to cyclize these compounds by intramolecular elimination of water into tricyclic compounds 6 with various dehydrating agents were unsuccessful.

📜 SIMILAR VOLUMES

Solid-phase synthesis of 1,2,4-triazolid
Solid-phase synthesis of 1,2,4-triazolidine-3,5-diones
✍ Kyung-Ho Park; Linda J Cox 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 56 KB

A traceless synthesis of 1,2,4-triazolidine-3,5-diones has been achieved through cyclo-elimination from solid-phase. This traceless cyclo-elimination release step is induced by catalytic amount of base or by simply refluxing the urea carbamate intermediate.