Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization of 2-(1-Alkynyl)benzamides for the Synthesis of Isoindolin-1-ones.

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2019
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Abstract
Phosphazene superbase P- t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65-97% yields, in a regio- and stereoselective manner. The exclusive formation of products with Z-geometry (across the exo C═C bond) has been confirmed through X-ray crystallography. The methodology also provides an easy access to aristolactams, an important class of natural products. This has been successfully demonstrated by synthesizing two aristolactam derivatives (including Cepharanone B).
Reference Key
mehta2019phosphazenethe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Mehta, Saurabh;Brahmchari, Dhirendra;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b00452
URL
Keywords
aristolochic acid upper tract urothelial carcinoma aristolochia species balkan endemic nephropathy aristolochic acid nephropathy

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