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Synthesis of 2,3-dihydro-1H-pyrroles by intramolecular cyclization of N-(3-butynyl)-sulfonamides

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Abstract

Hydroamination of 3-butynamine derivatives to give non-aromatic 2,3-dihydropyrroles was achieved by using PdCl2 or AuCl as the catalyst. With microwave-assisted heating, up to 92% isolated yield was obtained from this intramolecular 5-endo-dig cyclisation. The cyclopentane- and cyclohexane-fused 2,3-dihydropyrroles were transformed into the corresponding N-tosyl-pyrrolidine-2-carboxylic acids.

Graphical abstract: Synthesis of 2,3-dihydro-1H-pyrroles by intramolecular cyclization of N-(3-butynyl)-sulfonamides

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Publication details

The article was received on 02 Mar 2017, accepted on 05 Apr 2017 and first published on 05 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00528H
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of 2,3-dihydro-1H-pyrroles by intramolecular cyclization of N-(3-butynyl)-sulfonamides

    M. Chung, Y. Chan, W. Chang and D. Hou, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00528H

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