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Updated: Aug 19, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Radical Cyclopropanol Ring Opening Initiated Tandem Cyclizations for Efficient Synthesis of Phenanthridines and
Dexter C Davis1, Christopher W Haskins1, Mingji Dai1
1Department of Chemistry and Center for Cancer Research, Purdue University, West Lafayette, Indiana, 47907, United States.
Abstract:
β-Keto radicals can be readily generated from single-electron oxidation and ring opening of cyclopropanols. Herein, we report new ways of trapping β-keto radicals derived from Mn(III)-mediated oxidative cyclopropanol ring opening with biaryl isonitriles and N-aryl acrylamides derived from anilines. Through tandem radical cyclization processes, substituted phenanthridines and oxindoles can be synthesized in one step and good to excellent yield. These new synthetic methods feature broad substrate scope and mild reaction conditions, efficiently form two carbon-carbon bonds, and use cheap and commercially available manganese salts as oxidants. Concomitant installation of ketone functionality in the final products provides a handle for further functionalization of these important and biologically relevant scaffolds.
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