Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide

Wenteng Chen, Jiaan Shao, Zhi Li, Marc A. Giulianotti, Yongping Yu

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

A facile synthesis of polysubstituted pyrroles from tosylmethyl isocyanide (TOSMIC) and readily synthesized vinyl azides was developed. The reaction proceeded under mild conditions in the presence of base. 2-Tosyl-substituted pyrroles were obtained in moderate to good isolated yields. Additionally, a base-initiated one-pot pyrrole synthesis also was developed using carboxaldehydes, ethyl 2-azidoacetate, and TOSMIC.

Original languageEnglish (US)
Pages (from-to)214-221
Number of pages8
JournalCanadian Journal of Chemistry
Volume90
Issue number2
DOIs
StatePublished - Feb 2012
Externally publishedYes

Keywords

  • 2,3,4-trisubstituted pyrroles
  • Cyclization reaction
  • Multicomponent reaction
  • Nucleophilic reaction
  • Vinyl azides

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