Copper catalyzed aerobic oxidative cyclization and ketonization: one pot synthesis of benzoimidazo[1,2-a]imidazolones.

Chem Commun (Camb)

Department of Applied Chemistry, National Chiao-Tung University, 1001, Ta-Hseuh Road, Hsinchu 300-10, Taiwan, Republic of China. and Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100, Shih-Chuan 1st Road, Kaohsiung 807-08, Taiwan, Republic of China.

Published: May 2016

A highly efficient synthesis of benzoimidazo[1,2-a]imidazolone through a novel oxidative 5-exo-dig cyclization-ketonization cascade of 2-aminobenzimidazole, aldehyde and terminal alkyne has been explored under aerobic conditions. The reaction proceeds through copper-catalyzed addition of terminal alkynes to imines derived from 2-aminobenzimidazole with aldehyde followed by intramolecular cyclization. The atmospheric molecular oxygen acts as an oxygen source for the newly formed carbonyl group in the final product.

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http://dx.doi.org/10.1039/c6cc01828aDOI Listing

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