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Studies with 2-arylhydrazononitriles: Further investigations on reactivity of 2-arylhydrazononitriles towards hydroxylamine

✍ Scribed by Sayed M. Riyadh; Hamad M. Al-Matar; Mohamed H. Elnagdi

Book ID: 102341259
Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 333 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450405

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✦ Synopsis

Abstract

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The utilization of arylhydrazononitriles (6‐9) for synthesis of azoles is demonstrated. Thus, arylazomalononitriles (6) reacted with hydroxylamine hydrochloride to afford isoxazol‐5‐imine (10), amidoxime (12) and bis‐amidoxime (13) derivatives depending upon both the reaction conditions and molar ratio employed. 2‐Thiazolyl‐2‐arylhydrazononitriles (7) and cyanoformazans (8) gave 1,2,3‐triazole derivatives (15) and (17) respectively upon treatment with hydroxylamine hydrochloride and concomitant loss of water molecule. Formation of novel 1,2,4‐triazin‐5(4__H__)‐one derivatives (21) has efficiently been carried out by treatment of amidoximes (18) with acetic anhydride in acetic acid.

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