800394-49-4Relevant academic research and scientific papers
Highly selective conversion of N-aroyl-α-dehydronaphthylalaninamides into 3,4-dihydrobenzoquinolinone derivatives via photoinduced intermolecular electron transfer
Maekawa, Kei,Shinozuka, Ayana,Naito, Michiko,Igarashi, Tetsutaro,Sakurai, Tadamitsu
, p. 10293 - 10304 (2004)
The irradiation of substituted (Z)-N-aroyl-α- dehydronaphthylalaninamides [(Z)-1] in methanol containing triethylamine (TEA) with Pyrex-filtered light was found to give 3,4-dihydrobenzoquinolinone derivatives (2) in high yields along with minor amounts of 4,5-dihydrooxazole derivatives (3). Analysis of the substituent effects on product composition revealed that both the photoreactivity of 1 and the selectivity of 2 are decreased with increasing electron-withdrawing ability of the substituent introduced at the para-position on the N-benzoyl benzene ring. From the analysis of the dependence of the quantum yield for the formation of 2 on the TEA concentration, it was found that back electron transfer occurs efficiently within an (E)-1 anion radical-TEA cation radical pair intermediate. Graphical Abstract
