Synthesis of 3-Hydroxyisoindolin-1-ones through 1,4-Dioxane-Mediated Hydroxylhydrative aza-Cyclization of 2-Alkynylbenzamide in Water

• DOI: 10.1021/acs.joc.9b03466
• Publication Date: 2020-03-31T10:47:55Z
• Authors: Renzhi Liu; Min Yang; Wenlin Xie; Wenbi Dong; Hongwei Zhou; Sarita Yadav; Vladimir Ivanovic...; Guanyinsheng Qiu
• Keywords: Alkene; Radical cyclization; Scope (computer science)

In this work, 1,4-dioxane-mediated hydroxylhydrative aza-cyclization of 2-alkynylbenzamide is developed for the synthesis 3-hydroxylisoindolin-1-ones. The transformation proceeds smoothly in water with good yields and a broad reaction scope. Mechanistic studies show that regioselective brimonative 5-exo-dig aza-cyclization, bromohydration resulting alkene groups, hydrolysis dibromo compounds are involved. Compared to traditional methodologies, synthetic procedure reported herein represents cleaner route toward