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Synthesis of novel heterocycles using 1,2,3‐triazole‐4‐carbohydrazides as precursors

Mohamed, Hanan A., Khidre, Rizk E., Kariuki, Benson M. and El-Hiti, Gamal A. 2020. Synthesis of novel heterocycles using 1,2,3‐triazole‐4‐carbohydrazides as precursors. Journal of Heterocyclic Chemistry 57 (3) , pp. 1055-1062. 10.1002/jhet.3840

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Herein, we report the synthesis of various heterocyclic ring systems containing 1,2,3‐triazole from the reactions of acid hydrazides and commercially available reagents, using efficient and simple procedures. Reactions of certain 1,2,3‐triazole‐4‐carbohydrazides and α‐bromoketones in boiling ethanol afforded the corresponding hydrazones rather than the expected triazines. The hydrazones could also be synthesized in 85‐90% yield via an alternative pathway that involved the reaction of 1,2,3‐triazole‐4‐carbohydrazides and 4‐acetyl‐1,2,3‐triazoles in boiling ethanol containing glacial acetic acid. Reaction of one of the 4‐carbohydrazides with carbon disulfide, followed by the reaction with hydrazine hydrate, gave 4H‐1,2,4‐triazole‐3‐thiol in 73% yield, which further reacted with other α‐bromoketones in boiling ethanol to afford 7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines in 82‐84% yields. Additionally, reactions of certain carbohydrazides with ethyl 2‐cyano‐3,3‐bis(methylthio)acrylate gave 1‐aryl‐1H‐1,2,3‐triazole‐4‐carbohydrazides rather than the expected 1H‐pyrazole‐4‐carboxylates.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 0022-152X
Date of First Compliant Deposit: 9 January 2020
Date of Acceptance: 17 November 2019
Last Modified: 07 Dec 2020 17:04

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