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

Ryan A. Hawkins, Chad E. Stephens

Research output: Contribution to journalArticle

4 Citations (Scopus)

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
StatePublished - Nov 24 2010

Fingerprint

Quinazolines
Hydroxylation
Pyrroles
Oxygenation
Epoxidation
Acetone
Esters
Air
X-Rays
Oxygen
X rays
Crystals

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions. / Hawkins, Ryan A.; Stephens, Chad E.

In: Tetrahedron Letters, Vol. 51, No. 47, 24.11.2010, p. 6129-6131.

Research output: Contribution to journalArticle

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