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

Justin M. Lopchuk; Mia Song; Blythe Butler; Gordon W. Gribble

doi:10.1055/s-0034-1380720

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(18): 2776-2780
DOI: 10.1055/s-0034-1380720

special topic

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

Autoren

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

Abstract

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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.

Key words

cycloaddition - heterocycles - pyrroles - regioselectivity - münchnone

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Referenzen

References
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