Synthesis of some new five membered heterocycles, a facile synthesis of oxazolidinones

✍ Scribed by Ahmet Demirbas; Sule Ceylan; Neslihan Demirbas

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2007
• Tongue: English
• Weight: 558 KB
• Volume: 44
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570440608

✦ Synopsis

Abstract

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The synthesis and structural properties of two kinds of thiosemicarbazide derivatives (2a‐c and 3a‐c) and one kind of semicarbazide derivatives (4a, 4b) have been described. These compounds were synthesized by treating 2‐(4‐amino‐3‐alkyl‐5‐oxo‐4,5‐dihydro‐1__H__‐1,2,4‐triazol‐1‐yl)acetohydrazides (1a‐c) with benzyl isothiocyanate, 3‐florophenyl isothiocyanate and benzylisocyanate, respectively. The synthesis of 4‐amino‐3‐alkyl‐1‐[(4‐alkyl‐5‐mercapto(or 5‐oxo)‐4__H__‐1,2,4‐triazol‐3‐yl)methyl]‐4,5‐dihydro‐1__H__‐1,2,4‐triazol‐5‐ones (5a‐c, 6a‐c and 7) have been performed from the reaction with sodium hydroxide. On the other hand, the acidic treatment of compounds 2b, 3b and 4b has afforded 4‐amino‐3‐(4‐chlorobenzyl)‐1‐[(5‐alkylamino‐1,3,4‐thidazol(or 1,3,4‐oxazol)‐2‐yl)methyl]‐4,5‐dihydro‐1__H__‐1,2,4‐triazol‐5‐ones (8, 9 and 10). The condensation of thiosemi(or semi)carbazide derivatives (2a‐c, 3c and 4b) with 4‐chlorophenacylbromide have resulted in the formation of 2‐[4‐amino‐3‐alkyl‐5‐oxo‐4,5‐dihydro‐1__H__‐1,2,4‐triazol‐1‐yl]‐N′‐(3,4‐dialkyl‐1,3‐thiazol(or oxazol)‐2(3__H__)‐yliden]acetohydrazides (11a‐c, 12, 13), while their condensation with chloroacetic acid has produced 2‐[4‐amino‐3‐alkyl‐5‐oxo‐4,5‐dihydro‐1__H__‐1,2,4‐triazol‐1‐yl]‐N′‐[3‐(3‐alkyl)]‐4‐oxo‐1,3‐thiazolidin(or oxazolidin)‐2‐yliden}acetohydrazides (14, 15 and 16). The spectral data and elemental analyses have support the proposed structures.