Facile Conversions of Carboxylic Acids into Amides, Esters, and Thioesters Using 1, 1'-Oxalyldiimidazole and 1, 1'-Oxalyldi (1, 2, 4-triazole)

TOKUJIRO KITAGAWA; HIROKO KURODA; HIDEAKI SASAKI; KOICHI KAWASAKI

doi:10.1248/cpb.35.4294

TOKUJIRO KITAGAWA, HIROKO KURODA, HIDEAKI SASAKI, KOICHI KAWASAKI

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Keywords: 1, 1'-oxalyldiimidazole, 1, 1'-oxalyldi (1, 2, 4-triazole), 1, 1'-carbonyldiimidazole, l-acylazole, condensing reagent, amidation, esterification, dipeptide, aminolysis, alcoholysis

JOURNAL FREE ACCESS

1987 Volume 35 Issue 10 Pages 4294-4301

DOI https://doi.org/10.1248/cpb.35.4294

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Abstract

Aliphatic, aromatic, and heteroaromatic carboxylic acids react with 1, 1'-oxalyldiimidazole (1) or 1, 1'-oxalyldi (1, 2, 4-triazole) (2) in acetonitrile for 40min at 40 °C to give the corresponding 1-acylazole intermediates (11), which promptly undergo aminolysis and alcoholysis to form amides (13) including dipeptides (14), esters (16), and thioesters (19). These findings show that both 1 and 2 can be utilized as condensing reagents for the synthesis of carboxylic acid derivatives.

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