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Issue 38, 2015
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Metal/organo relay catalysis in a one-pot synthesis of methyl 4-aminopyrrole-2-carboxylates from 5-methoxyisoxazoles and pyridinium ylides

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Abstract

Methyl 4-aminopyrrole-2-carboxylates were synthesized in one-pot mode by the relay catalytic cascade reaction of 5-methoxyisoxazoles with pyridinium ylides by the use of a FeCl2/Et3N binary catalytic system leading to 1-(5-methoxycarbonyl-1H-pyrrol-3-yl)pyridinium salts followed by hydrazinolysis. The approach permits the introduction of a substituent at the pyrrole nitrogen via a nucleophilic reaction of the pyrrolylpyridinium ylide derived from the salt. Catalytic reduction of the ylides gives methyl 4-piperidinopyrrole-2-carboxylates.

Graphical abstract: Metal/organo relay catalysis in a one-pot synthesis of methyl 4-aminopyrrole-2-carboxylates from 5-methoxyisoxazoles and pyridinium ylides

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Supplementary files

Article information


Submitted
24 Jul 2015
Accepted
07 Aug 2015
First published
07 Aug 2015

Org. Biomol. Chem., 2015,13, 9825-9833
Article type
Paper
Author version available

Metal/organo relay catalysis in a one-pot synthesis of methyl 4-aminopyrrole-2-carboxylates from 5-methoxyisoxazoles and pyridinium ylides

E. E. Galenko, O. A. Tomashenko, A. F. Khlebnikov and M. S. Novikov, Org. Biomol. Chem., 2015, 13, 9825
DOI: 10.1039/C5OB01537E

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