Synthesis of benzoxazoles via an amine-catalyzed [4 + 1] annulation

Aiguo Song, Xiaobei Chen, Xixi Song, Xinshuai Zhang, Shilei Zhang, Wei Wang

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

An unprecedented simple pyrrolidine catalyzed [4 + 1] annulation reaction of ynals with N-protected-2-aminophenols is reported. The utilization of the unique property and reactivity of the C=C triple bond in ynals leads to two consecutive conjugate addition reactions at the same β-position with pyrrolidine via iminium activation. The powerful cascade process affords a new alternative approach to biologically and synthetically important benzoxazoles in high yields (83-95%).

Original languageEnglish (US)
Pages (from-to)2510-2513
Number of pages4
JournalOrganic Letters
Volume15
Issue number10
DOIs
StatePublished - May 17 2013
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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