Synlett 2017; 28(17): 2241-2246
DOI: 10.1055/s-0036-1590686
letter
© Georg Thieme Verlag Stuttgart · New York

A New Synthesis of Pyrroles from Benzimidazolium N-Cyanomethyl Ylides and Alkyne Dipolarophiles

Denisa Dumitrescua, Emilian Georgescub, Mino R. Caira*c, Constantin Draghicid, Florea Dumitrascu*d
  • aFaculty of Pharmacy, University Ovidius, Aleea Universitatii 1, Constantza, Romania
  • bOltchim Research Center, St. Uzinei 1, 230050 Ramnicu Valcea, Romania
  • cDepartment of Chemistry, University of Cape Town, Rondebosch 7701, South Africa   Email: Mino.Caira@uct.ac.za
  • dCenter of Organic Chemistry ‘C. D. Nenitzescu’, Romanian Academy, Spl. Independentei 202B, Bucharest 060023, Romania   Email: fdumitra@yahoo.com
M.R.C. thanks the University of Cape Town and the NRF (Pretoria) for financial support.
Further Information

Publication History

Received: 28 April 2017

Accepted after revision: 06 June 2017

Publication Date:
19 July 2017 (eFirst)

Abstract

A straightforward synthesis of highly functionalized pyrroles was achieved by a one-pot reaction between 3-(cyanomethyl)benzimidazolium salts and acetylenic dipolarophiles under reflux in 1,2-epoxybutane. The new pyrroles can also be obtained by a one-pot three-component reaction from substituted benzimidazoles, bromoacetonitrile, and activated acetylenes. The structures of the pyrroles were deduced by NMR spectroscopy and confirmed by X-ray crystal analysis.

Supporting Information