T. Sakurai, Kei Maekawa, H. Kajiwara
Mar 1, 2003
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0
Influential Citations
11
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Journal
Heterocycles
Abstract
On irradiation in methanol, the title compounds having chloro, trifluoromethyl or methyl group at the meta position on the styryl benzene ring gave 6-substituted (2) and 8-substituted (3) 1-methyl-3-(methylaminocarbonyl)isoquinolines along with 1-azetines. The preferential formation of 2 to 3 was explained in terms of steric effects on the cyclization process from the excited-state (Z)-isomer. The methoxy group introduced at the same meta position exerted dramatical electronic and steric effects on the excited-state cyclization pathway giving rise to regioselectively 6-substituted 2-quinolinone and isoquinoline derivatives. The 1-naphthyl substituent in the title compounds was found to have the same effects on the cyclization pathway as the methoxyphenyl group.