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Paper | Regular issue | Vol 104, No. 4, 2022, pp.751-763
Published online, 19th January, 2022
DOI: 10.3987/COM-21-14612
Alicyclic Annulated Triazoles versus Triazinediones by the Reaction of Cyclic Imidates with Methyl 2-Hydrazinyl-2-oxoacetate

Viacheslav Lysenko, Anton Portiankin, Kostiantyn Nazarenko, Kostiantyn Shvydenko, Tetiana Shvydenko, and Aleksandr Kostyuk*

*Organophosphorus, Institute of Organic Chemistry, Murmanska Str.5, 02660, Ukraine

Abstract

A simple convenient method for synthesis of esters of annulated triazole-3-carboxylic acids and/or 1,2,4-triazine-5,6-dione derivatives was proposed. Heating cyclic imidates with methyl 2-hydrazinyl-2-oxoacetate afforded either the annulated triazoles or the annulated triazinediones depending on the reaction conditions. Under heating at hydrochloric acid 1,2,4-triazine-5,6-diones were transformed into triazoles.