A new regioselective synthesis and ambient light photochemistry of quinazolin-1-oxides

Coskun N., Cetin M.

TETRAHEDRON, vol.63, no.14, pp.2966-2972, 2007 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 63 Issue: 14
  • Publication Date: 2007
  • Doi Number: 10.1016/j.tet.2007.02.004
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2966-2972
  • Keywords: N-oxides, quinazoline, quinazolin-1-ol, quinazolin-1-oxide, qui nazolin-3-oxide, quinazolin-4(3H)-one, ambient light photochemistry, rearrangement, photochemical deoxygenation, solvent effect, solvent isotope effect, RING-CHAIN TAUTOMERISM, ACRIDONE ALKALOIDS, N-OXIDES, QUINAZOLINES, QUINOLINE, 1,4-BENZODIAZEPINES, INHIBITORS
  • Bursa Uludag University Affiliated: Yes

Abstract

Quinazolin-1-oxides were prepared by the oxidation of tetrahydroquinazolines with H2O2-tungstate and their ambient light photochemistry was investigated. Substituent effects on their photochemical cyclization and the reactions of the products 1aH- [1,2]oxazireno[2,3-a]quinazolines under photochemical and thermal conditions are reported. The cyclization of quinazolin-1-oxides and the reactions of 1aH-[1,2]oxazireno[2,3-a]quinazolines show pronounced solvent isotope and solvent effects. (c) 2007 Published by Elsevier Ltd.