Direct synthesis of esters and amides from unprotected hydroxyaromatic and -aliphatic carboxylic acids

作者：Katritzky AR^*; Singh SK; Cai CM; Bobrov S

来源：Journal of Organic Chemistry, 2006, 71(9): 3364-3374.

DOI：10.1021/jo052293q

A facile method for the activation of hydroxy-substituted carboxylic acids using benzotriazole chemistry without prior protection of the hydroxy substituents is presented. The N-acylbenzotriazole intermediates 2a-g, 6a-d, and 9a-c have been used for high-yielding, synthesis of both aliphatic (3a-1) and aromatic (7a-h, 10a-f) hydroxy carboxamides. High yields of aromatic hydroxy esters 12a-h and 13a-i were obtained using either neat alcohols in neutral microwave conditions or nucleophilic alkoxides and the intermediate N-(arylacyl)benzotriazoles. Moderate yields were obtained in the case of aliphatic hydroxy esters 11a,b and thiolesters 11e-g from the intermediates 2a-c.

• 出版日期2006-4-28