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One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence

Dennis Imbri, Natalie Netz, Murat Kucukdisli, Lisa Marie Kammer, Philipp Jung, Annika Kretzschmann and Till Opatz*

*Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany, Email: opatzuni-mainz.de

D. Imbri, N. Netz, M. Kucukdisli, L. M. Kammer, P. Jung, A. Kretzschmann, T. Opatz, J. Org. Chem., 2014, 79, 11750-11758.

DOI: 10.1021/jo5021823 (free Supporting Information)


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Abstract

An electrocyclic ring closure is the key step of an efficient one-pot synthesis of pyrrole-2-carboxylates and -carboxamides from chalcones and glycine esters or amides. The resulting 3,4-dihydro-2H-pyrrole intermediates are oxizided to the corresponding pyrroles by stoichiometric oxidants or by catalytic copper(II) and air in good yields.

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Key Words

pyrroles, DDQ


ID: J42-Y2014