二取代咪唑并[4,5-b]吡啶-2-酮的合成。

Synthesis of disubstituted imidazo[4,5-b]pyridin-2-ones.

作者信息

Kuethe Jeffrey T, Wong Audrey, Davies Ian W

机构信息

Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA.

出版信息

J Org Chem. 2004 Oct 29;69(22):7752-4. doi: 10.1021/jo048887v.

DOI:10.1021/jo048887v

PMID:15498009

Abstract

Regioselective palladium-catalyzed amination of 2-chloro-3-iodopyridine followed by a subsequent palladium-catalyzed amination leads to 2,3-diaminopyridines. Treatment with triphosgene affords highly functionalized unsymmetrical imidazo[4,5-b]pyridin-2-ones in just three synthetic steps. A two-step synthesis of pseudosymmetrically disubstituted imidazo[4,5-b]pyridin-2-ones, 1,4-disubstituted pyrido[2,3-b]pyrazinediones, and 1,3-disubstituted thiadiazolo[3,4-b]pyridin-2-ones is also described.

摘要

2-氯-3-碘吡啶的区域选择性钯催化胺化反应，随后进行钯催化胺化反应，生成2,3-二氨基吡啶。用三光气处理，只需三个合成步骤就能得到高度官能化的不对称咪唑并[4,5-b]吡啶-2-酮。还描述了伪对称二取代咪唑并[4,5-b]吡啶-2-酮、1,4-二取代吡啶并[2,3-b]吡嗪二酮和1,3-二取代噻二唑并[3,4-b]吡啶-2-酮的两步合成法。