Synthesis 2015; 47(18): 2776-2780
DOI: 10.1055/s-0034-1380720
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Heteroaryl-Substituted Pyrroles via the 1,3-Dipolar Cycloaddition of Unsymmetrical Münchnones and Nitrovinylheterocycles

Justin M. Lopchuk
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA   Email: ggribble@dartmouth.edu
,
Mia Song
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA   Email: ggribble@dartmouth.edu
,
Blythe Butler
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA   Email: ggribble@dartmouth.edu
,
Gordon W. Gribble*
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA   Email: ggribble@dartmouth.edu
› Author Affiliations
Further Information

Publication History

Received: 12 March 2015

Accepted after revision: 16 April 2015

Publication Date:
19 May 2015 (eFirst)

Abstract

A series of furanyl-, thiophenyl-, and pyrrolo-substituted pyrroles were prepared via the 1,3-dipolar cycloaddition of unsymmetrical münchnones and nitrovinylheterocycles. The regiochemical outcome of the furan and thiophene cycloadditions compares favorably to previously reported cycloadditions with β-nitrostyrene, while the nitrovinylpyrrole cycloadditions mirror the results observed with nitrovinylindole.

 
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