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Communication | Special issue | Vol 77, No. 2, 2009, pp.739-746
Published online, 9th September, 2008
DOI: 10.3987/COM-08-S(F)53
Novel Photoinduced Electron Transfer-initiated Cyclization of 1,2,4-Triazole-substituted α-Dehydronaphthylalaninamides in the Presence of Triethylamine

Kei Maekawa, Atsushi Tomod, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

The irradiation of the title compounds [(Z)-1] in nitrogen-saturated methanol containing triethylamine (TEA) at room temperature was found to quantitatively afford 2(1H)-benzo[f]quinolinone (2) and 3,4-dihydro-3-(3-methyl-5-substituted 1,2,4-triazol-4-yl)-2(1H)-benzo[f]quinolinone (3) derivatives, which were described as being formed via electron transfer from TEA to the excited-state (E)-1. Analysis of solvent and substituent effects on the composition ratio of 2 to 3 confirmed that this ratio is increased from 0.2 to 9.0 with an increase in the proton-donating ability and polarity of solvent as well as in the electron-withdrawing ability of substituent bonded to the triazole ring.