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.
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Original Russian Text © N.T. Pokhodylo, O.Ya. Shyyka, R.D. Savka, M.D. Obushak, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 7, pp. 1083–1091.
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Pokhodylo, N.T., Shyyka, O.Y., Savka, R.D. et al. 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. Russ J Org Chem 54, 1090–1099 (2018). https://doi.org/10.1134/S1070428018070205
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DOI: https://doi.org/10.1134/S1070428018070205