Approach to phenanthroindolizidine alkaloids using organic azides with 1- Aryl allylic alcohols: Unexpected tandem reactions to indenyl aziridines via nazarov cyclization

Taiki Yokoi, Takahiro Sugiura, Hiroki Tanimoto, Tsumoru Morimoto, Yasuhiro Nishiyama, Kiyomi Kakiuchi

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Organic azide cyclization reactions with 1- Aryl allylic alcohols were investigated in a synthetic study of phenanthroindolizidine alkaloids. Unsaturated imines (enimines) were effectively obtained from the allylic alcohol adjacent to electron-rich aromatic rings under thermal reaction conditions. The tandem aziridination-Nazarov reactions to indenyl aziridines were preferred to the acid-mediated enimine formation via Schmidt reaction in the case of 3- Aryl diallylic alcohols.

Original languageEnglish
Pages (from-to)1313-1327
Number of pages15
JournalHeterocycles
Volume92
Issue number7
DOIs
StatePublished - 2016

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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