Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 6, Pages 3339-3347Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02903
Keywords
-
Categories
Funding
- Delhi Technological University
- SERB [SB/S1/OC-84/2013]
Ask authors/readers for more resources
A simple and straightforward synthesis of isoindolin-l-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-2/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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available