One-Pot Multicomponent Mechanosynthesis of Polysubstituted trans-2,3-Dihydropyrroles and Pyrroles from Amines, Alkyne Esters, and Chalcones

Hui Xu, Hong-Wei Liu, Kuan Chen and Guan-Wu Wang*

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China, Email: gwangustc.edu.cn

H. Xu, H.-W. Liu, K. Chen, G.-W. Wang, J. Org. Chem., 2018, 83, 6035-6049.

DOI: 10.1021/acs.joc.8b00665

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Abstract

The combination of I₂/PhI(OAc)₂ promotes an efficient and practical one-pot reaction of amines with alkyne esters and chalcones under solvent-free ball-milling conditions to afford a variety of polysubstituted trans-2,3-dihydropyrroles in good yields. This protocol furnishes the corresponding pyrroles with the addition of DDQ as oxidant in a subsequent step.

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Key Words

dihydropyrroles, pyrroles, PIDA, iodine, DDQ, mechanochemistry

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ID: J42-Y2018