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

Department of Chemistry, University of Durham, South Road, DH13LE, United Kingdom
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Molbank 2017, 2017(3), M951; https://doi.org/10.3390/M951
Received: 27 July 2017 / Revised: 1 August 2017 / Accepted: 2 August 2017 / Published: 4 August 2017
(This article belongs to the Section Organic Synthesis)
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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MDPI and ACS Style

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

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