Photoreaction of 2′-chloro-4-R-benzanilide: Synthesis of 2-(4-R-phenyl)-1,3-benzoxazole and 9-R-phenanthridin-6(5H)-one (R=H, CH3, CH3O)

Ahmed M. Mayouf, Yong Tae Park

Research output: Journal PublicationArticlepeer-review

11 Citations (Scopus)

Abstract

The UV photolysis of2′-chloro-4-R-benzanilides in acetonitrile solution under nitrogen atmosphere leads to the formation of intramolecular photocyclization products (9-R-phenanthridin-6(5)-one, 20-30%), along with the minor photoreduction, photo-Fries, and intramolecular photosubstitution products. The photoreaction of 2′-chloro-4-R-benzanilide in acetonitrile solution containing 10% of water or aqueous sodium hydroxide however gives 2-(4-R-phenyl)-1,3-benzoxazole as a major product (∼30%) along with the photoreduction, photo-Fries and intramolecular photocyclization products.

Original languageEnglish
Pages (from-to)115-123
Number of pages9
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume150
Issue number1-3
DOIs
Publication statusPublished - 26 Jul 2002
Externally publishedYes

Keywords

  • 2′-chloro-4-R-benzanilides
  • Intramolecular photocyclization
  • Intramolecular photosubstitution
  • Solvent and substituent effect

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering
  • General Physics and Astronomy

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