Acid-catalyzed reaction of 3-aminopyrrole with s-tetrazines: Formation of 1H-1,2,4-(triazol-3-yl)pyrimidines via an unprecedented s-tetrazine-ring contraction and concomitant pyrrole-ring expansion

Michael De Rosa, David Arnold, Hemant Yennawar

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Initial reaction of 3-aminopyrrole with the conjugate acid of 3,6-diphenyl-1,2,4,5-tetrazine gave an intermediate that rearranged to a 1H-1,2,4-(triazol-3-yl)pyrimidine via an unprecedented cascade. In this cascade, the s-tetrazine-ring opened, contracted to a 1,2,4-triazole-ring, and the pyrrole ring expanded to a pyrimidine. Similar results were obtained with three other electronically different s-tetrazines.

Original languageEnglish (US)
Pages (from-to)5491-5494
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number40
DOIs
StatePublished - Oct 1 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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