✦ LIBER ✦

Convenient syntheses of 5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-oxadiazole-2(3H)thione and N-substituted 2-amino-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-thiadiazoles

✍ Scribed by Javad Mirzaei; Hooshang Pirelahi; Mohsen Amini; Abbas Shafiee

Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 268 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450343

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✦ Synopsis

Abstract

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Oxidation of metronidazole (4) with sodium dichromate yielded the corresponding 2‐(2‐methyl‐5‐nitro‐1__H__‐imidazol‐1‐yl)acetic acid (5) which was esterified with 1‐butanol to give butyl 2‐(2‐methyl‐5‐nitro‐1__H__‐imidazol‐1‐yl)acetate (8). Reaction of the latter with hydrazine hydrate gave 2‐(2‐methyl‐5‐nitro‐1__H__‐imidazol‐1‐yl)acetohydrazide (9). Compound 5‐[(2‐methyl‐5‐nitro‐1__H__‐imidazol‐1‐yl)methyl]‐1,3,4‐oxa‐diazole‐2(3__H__)‐thione (10) could be obtained through the reaction of compound 9 with carbon disulfide in basic medium. Subsequent alkylation of compound 10 afforded alkyl 2‐(5‐[(2‐methyl‐5‐nitro‐1__H__‐imidazol‐1‐yl)methyl]‐1,3,4‐oxadiazol‐2‐ylthio)acetate (11) in good yield. Reaction of hydrazide 9 with substituted isothiocynate yielded 1‐[2‐(2‐methyl‐5‐nitro‐1__H__‐imidazol‐1‐yl)acetyl]‐4‐aryl(or ethyl)thiosemicarbazide (12) which was cyclized in acidic media to N‐substituted 2‐amino‐5‐[(2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl]‐1,3,4‐thiadiazole (13).

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