通过硝酮对1,3-烯炔的串联区域选择性加成并随后重排合成高度取代的2,3-二氢-1H-吡咯衍生物。

Synthesis of highly substituted 2,3-dihydro-1H-pyrrole derivatives via a tandem regioselective addition of nitrones to 1,3-enynes with subsequent rearrangement.

作者信息

Saravanan Sivaperuman, Azath Ismail Abulkalam, Muthusubramanian Shanmugam

机构信息

Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India.

出版信息

J Org Chem. 2008 Mar 21;73(6):2323-9. doi: 10.1021/jo702610j. Epub 2008 Feb 22.

DOI:10.1021/jo702610j

PMID:18290664

Abstract

A novel method for the synthesis of 1,3-enynes is described through oxidative cyclization of the semicarbazones of Michael adducts having potential nitrile functionality. Reaction of these 1,3-enynes with diaryl nitrones has yielded a diastereomeric mixture of highly substituted 2,3-dihydro-1H-pyrrole derivatives via a tandem regioselective addition with subsequent rearrangement.

摘要

描述了一种通过具有潜在腈官能团的迈克尔加成物的半缩酮的氧化环化来合成1,3-烯炔的新方法。这些1,3-烯炔与二芳基硝酮反应，通过串联区域选择性加成并随后重排，得到了高度取代的2,3-二氢-1H-吡咯衍生物的非对映体混合物。