Access to Pyrrolo-pyridines by Gold-catalyzed Hydroarylation of Pyrroles Tethered to Terminal Alkynes

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2012 Jan 13

PMID 22238519

Citations 1

Authors

Elena Borsini

Gianluigi Broggini

Andrea Fasana

Chiara Baldassarri

Angelo M Manzo

Alcide D Perboni

Affiliations

Soon will be listed here.

Abstract

In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicyclic pyrrolo-fused pyridinones by a 6-exo-dig process, while the presence of a phenyl group at the C-C triple bond promotes the 7-endo-dig cyclization giving pyrrolo-azepines.

Citing Articles

Merging gold and organocatalysis: a facile asymmetric synthesis of annulated pyrroles.

Hack D, Loh C, Hartmann J, Raabe G, Enders D Chemistry. 2014; 20(14):3917-21.

PMID: 24590817 PMC: 4238261. DOI: 10.1002/chem.201400407.

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