Mechanism of the inverse-electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid

Michael De Rosa, David Arnold

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur.

Original languageEnglish (US)
Pages (from-to)2975-2977
Number of pages3
JournalTetrahedron Letters
Volume48
Issue number17
DOIs
StatePublished - Apr 23 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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