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Molbank 2017, 2017(3), M951;

Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate

Department of Chemistry, University of Durham, South Road, DH13LE, United Kingdom
Author to whom correspondence should be addressed.
Received: 27 July 2017 / Revised: 1 August 2017 / Accepted: 2 August 2017 / Published: 4 August 2017
(This article belongs to the Section Organic Synthesis)
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This note describes a sequence converting an oxime-substituted pyrrolidine into a trisubstituted pyrrole structure. The synthetic route is based on a double chlorination of the pyrrolidine substrate followed by the base induced formation of both an imine and a nitrile oxide functionality. The latter reacts with an immobilized thiourea to yield an isothiocyanate which upon elimination generates the final pyrrole in an unprecedented cascade of events. View Full-Text
Keywords: pyrrole; pyrrolidine; heterocycle; rearrangement; isothiocyanate; chlorination pyrrole; pyrrolidine; heterocycle; rearrangement; isothiocyanate; chlorination

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Baumann, M.; Baxendale, I.R. Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate. Molbank 2017, 2017, M951.

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