On DABAL-Me3 promoted formation of amides

TETRAHEDRON

卷:69

Article

Dubois, Nathalie¹  Glynn, Daniel¹  McInally, Thomas¹  Rhodes, Barrie²  Woodward, Simon¹  Irvine, Derek J.³  Dodds, Chris³ 

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] Aesica Pharmaceut Ltd, Newcastle Upon Tyne NE12 8BS, Tyne & Wear, England

[3] Univ Nottingham, Dept Chem & Environm Engn, Nottingham NG7 2RD, England

关键词: Coupling agent;    Trimethylaluminium;    Amide;    Ester;    Carboxylic acid;    Microwave;   

DOI  :  10.1016/j.tet.2013.08.062

来源: Elsevier

【 摘 要 】

The range and utility of DABAL-Me-3 couplings of methyl esters and free carboxylic acids with primary and secondary amines under a variety of conditions (reflux, sealed tube, microwave) has been compared for a significant range of coupling partners of relevance to the preparation of amides of interest in pharmaceutical chemistry. Commercial microwave reactors promote the fastest couplings and allow the use of significantly sterically hindered amines (primary and secondary) and carboxylic acids derivatives. The influence of microwave energy on the reaction system was shown to be typically related to thermal effects (over-pressuring and superheating). (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

Free