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Communication | Special issue | Vol 80, No. 1, 2010, pp.199-206
Published online, 19th August, 2009
DOI: 10.3987/COM-09-S(S)55
Substituent Effects on the Electron Transfer-Initiated Photochemical Transformation of 1,2,4-Triazole-substituted α-Dehydroarylalaninamides into 2(1H)-Quinolinone Derivatives

Yuichi Yazawa, Minoru Suzuki, Tetsutaro Igarashi, and Tadamitsu Sakurai*

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


An investigation was undertaken to elucidate substituent effects on the photoreactivity of 1,2,4-triazole-substituted α-dehydroarylalaninamides [(Z)-1] as well as on the selectivity of 2(1H)-quinolinone derivatives (2) from a synthetic point of view. It was found that photoinduced electron transfer-initiated cyclization of (Z)-1 bearing a meta-substituted phenyl or a 4-substituted naphthalen-1-yl group in methanol proceeds with a moderate to good efficiency affording the corresponding product 2 in a selectivity ranging from 33 to 100%.