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Paper | Regular issue | Vol 71, No. 2, 2007, pp.343-359
Published online, 29th December, 2006
DOI: 10.3987/COM-06-10944
Reaction of 1-Acyl and Aroyl-2-hydroxy-3,3-dimethylindolines with Arylamines Catalyzed by BF3·Etherate. Formation of Dihydroindolo[1,2-c]quinazoline

Akiko Watanabe, Koki Yamaguchi, Fumikazu Ito, Yasuyuki Yoshitake, and Kazunobu Harano*

*Laboratory of Molecular Design, Sojo University, 4-22-1, Ikeda, Kumamoto-shi, 860-0082, Japan


The reaction of (4-chlorophenyl)(2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-yl)methanone or 1-(2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone with 2-aminonaphthalene in the presence of excess amounts of BF3·Et2O gave the 14,14-dimethyl-14,14a-dihydrobenzo[f]indolo[1,2-c]quinazoline derivatives which are derived from the dehydrative cyclization of the coupling reaction product [2-(2-aminonaphthalen-1-yl)-3,3-dimethyl-2,3-dihydroindol-1-yl](4-chlorophenyl)methanone or 1-[2-(2-aminonaphthalen-1-yl)-3,3-dimethyl-2,3-dihydroindol-1-yl]ethanone. The reactions of several (2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-yl)(substitutedphenyl)methanones or 1-(2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone with m-anisidine gave the cyclization products together with the coupling reaction products. The structure of the cyclization product and the reaction mechanism are discussed based on the crystallographic and molecular orbital (MO) calculation data.