Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions

Ryan A. Hawkins, Chad E. Stephens

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4 Scopus citations

Abstract

A pyrrolo[2,1-b]quinazoline has been found to undergo both epoxidation and hydroxylation on the pyrrole nucleus upon simple exposure of an acetone solution to air or oxygen. The oxygenation reaction occurs most readily when the starting compound contains a t-butyl ester at the 3-position, compared to a cyano or phenylsulfonyl. The structure of the product has been confirmed by X-ray crystal analysis.

Original languageEnglish (US)
Pages (from-to)6129-6131
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number47
DOIs
Publication statusPublished - Nov 24 2010

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Keywords

  • Aerobic epoxidation
  • Aerobic hydroxylation
  • Pyrrole oxygenation
  • Pyrrolo[2,1-b]quinazoline
  • Singlet oxygen

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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