Facile conversions of carboxylic acids into amides, esters, and thioesters using 1, 1'-oxalyldiimidazole and 1, 1'-oxalyldi (1, 2, 4-triazole).

T KITAGAWA, H KURODA, H SASAKI…

Index: Kitagawa, Tokujiro; Kuroda, Hiroko; Sasaki, Hideaki; Kawasaki, Koichi Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 10 p. 4294 - 4301

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Citation Number: 21

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 ...

~88%

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