jo7b02903_si_002.cif (2.4 MB)

Regio- and Stereoselective Synthesis of Isoindolin-1-ones through BuLi-Mediated Iodoaminocyclization of 2‑(1-Alkynyl)benzamides

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posted on 19.02.2018, 00:00 by Dhirendra Brahmchari, Akhilesh K. Verma, Saurabh Mehta
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-I2/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.

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