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Short Paper | Regular issue | Vol 89, No. 7, 2014, pp.1678-1686
Published online, 4th June, 2014
DOI: 10.3987/COM-14-13010
Selective Photocyclization Reactions of (Z)-N-Acetyl-α-dehydro(9-phenanthryl)alanine Alkyl Esters and N′,N′-Dialkylamides to Dibenzo[f,h]isoquinoline Derivatives

Yuto Iijima, Tetsutaro Igarashi, and Tadamitsu Sakurai*

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

Abstract

(Z)-N-Acetyl-α-dehydro(9-phenanthryl)alanine alkyl esters and N′,N′-dialkylamides [(Z)-1] were synthesized, and their photocyclization behavior in methanol was explored. The irradiation of (Z)-1 in a protic polar solvent at wavelengths greater than 280 nm caused selective cyclization reactions, producing the corresponding dibenzo[f,h]isoquinoline derivatives. Moreover, the formation efficiency of these derivatives showed strong dependence on the steric bulk and electronic property of the alkoxycarbonyl and dialkylaminocarbonyl groups.