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

The Journal of Organic Chemistry
Alan R. KatritzkySergey Bobrov

Abstract

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-l) 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.

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Citations

Sep 8, 2011·Chemical Reviews·Alan R Katritzky, Stanislaw Rachwal
Aug 9, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tomas GonecJosef Jampilek
Oct 3, 2015·The Journal of Organic Chemistry·Scott E Denmark, Lindsey R Cullen
Jun 4, 2016·Chemistry : a European Journal·Joydeb Majumder, Parthasarathi Dastidar
Apr 2, 2010·Organic Letters·Gavin O'Mahony, Andrew K Pitts
Apr 27, 2007·The Journal of Organic Chemistry·Alan R KatritzkyPeter J Steel
Jan 29, 2013·The Journal of Organic Chemistry·Narsimha Mamidi, Debasis Manna
Dec 16, 2006·The Journal of Organic Chemistry·Alan R KatritzkyPrabhu P Mohapatra

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