Synthesis of 5-amino-3-(het)aryl-1H-1,2,4-triazoles via Cyclization of(het)aroylaminoguanidines in Aqueous Medium

Anton Dolzhenko; Hui-Shan Chia; Wai-Keung Chui

doi:10.3390/ecsoc-9-01484

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Synthesis of 5-amino-3-(het)aryl-1H-1,2,4-triazoles via Cyclization of(het)aroylaminoguanidines in Aqueous Medium

Anton V. Dolzhenko

^*,

Hui-Shan Chia

Wai-Keung Chui

¹ Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore

Published: 01 November 2005 by MDPI in The 9th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-9-01484

Abstract: The effective and clean procedure for the preparation of 5-amino-3-(het)aryl-1,2,4-triazoles (3a-c) via cyclization of (het)aroylaminoguanidines (2a-c) in water was reported. Two tautomeric forms, namely 5-amino-3-(het)aryl-1,2,4-triazoles (A) and 3-amino-5-(het)aryl-1,2,4-triazoles (B) were found to exist in tautomeric equilibrium. Form A was a predominant tautomer in DMSO solution (KT = 9-33).

Keywords: 1,2,4-triazoles; acylaminoguanidines; cyclization; aqueous medium; tautomerism

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Anton Dolzhenko

Hui-Shan Chia

Wai-Keung Chui