2-Azido-1,3,4-thiadiazoles, 2-Azido-1,3-thiazoles, and Aryl Azides in the Synthesis of 1,2,3-Triazole-4-carboxylic Acids and Their Derivatives


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Abstract

Diazotization of 2-amino-1,3,4-thiadiazoles gave 1,3,4-thiadiazole-2-diazonium sulfates which were converted to 2-azido-1,3,4-thiadiazoles. The latter reacted with ethyl acetoacetate in the presence of sodium methoxide in methanol to produce 1-(5-R1-1,3,4-thiadiazol-2-yl)-5-R2-1H-1,2,3-triazole-4-carboxylic acid derivatives. The reactions of 2-azido-5-methyl-1,3,4-thiadiazole and 2-azido-1,3-thiazole with ethyl 3-(1,3-benzodioxol-5-yl)-3-oxopropanoate led to the formation of 1,2,3-triazole ring under milder conditions (K2CO3, DMSO). Various 1,2,3-triazole-4-carboxylic acid derivatives were synthesized.

About the authors

N. T. Pokhodylo

Ivan Franko Lviv National University

Email: obushak@in.lviv.ua
Ukraine, ul. Kirilla i Mefodiya 6, Lviv, 79005

O. Ya. Shyyka

Ivan Franko Lviv National University

Email: obushak@in.lviv.ua
Ukraine, ul. Kirilla i Mefodiya 6, Lviv, 79005

R. D. Savka

Ivan Franko Lviv National University

Email: obushak@in.lviv.ua
Ukraine, ul. Kirilla i Mefodiya 6, Lviv, 79005

M. D. Obushak

Ivan Franko Lviv National University

Author for correspondence.
Email: obushak@in.lviv.ua
Ukraine, ul. Kirilla i Mefodiya 6, Lviv, 79005

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