Department of Applied Chemistry , Delhi Technological University , Delhi , 110042 , India.
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry , University of Delhi , Delhi 110007 , India.
J Org Chem. 2018 Mar 16;83(6):3339-3347. doi: 10.1021/acs.joc.7b02903. Epub 2018 Feb 26.
A simple and straightforward synthesis of isoindolin-1-ones is reported. Exclusive N-cyclization of the amide functional group, an ambident nucleophile, was accomplished for the cyclization of 2-(1-alkynyl)benzamides using n-BuLi-I/ICl. The methodology works with the primary amide and affords the desired isoindolinones in yields of 38-94%. Interestingly, the isolated products exhibit a Z-stereochemistry across the C═C double bond. The reaction mechanism involving the formation of either a vinylic anion or an intimate ion pair intermediate is proposed.
报道了一种简单直接的异吲哚啉-1-酮合成方法。酰胺官能团作为两性亲核试剂，通过 n-BuLi-I/ICl 进行环化反应，实现了 2-（1-炔基）苯甲酰胺的 N-环化。该方法适用于伯酰胺，可在 38-94%的产率下得到所需的异吲哚啉酮。有趣的是，分离得到的产物在 C=C 双键处具有 Z 立体化学。提出了涉及形成乙烯基阴离子或紧密离子对中间体的反应机制。
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