Regio- and Stereoselective Synthesis of Isoindolin-1-ones through BuLi-Mediated Iodoaminocyclization of 2‑(1-Alkynyl)benzamides
datasetposted on 19.02.2018, 00:00 by Dhirendra Brahmchari, Akhilesh K. Verma, Saurabh Mehta
Datasets usually provide raw data for analysis. This raw data often comes in spreadsheet form, but can be any collection of data, on which analysis can be performed.
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 CC double bond. The reaction mechanism involving the formation of either a vinylic anion or an intimate ion pair intermediate is proposed.