K. Harano, A. Watanabe, K. Yamaguchi
Feb 1, 2007
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0
Influential Citations
5
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Journal
Heterocycles
Abstract
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 BF 3 ·Et 2 O 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-l-yl]ethanone. The reactions of several (2-hydroxy-3,3-dimethyl-2,3-dihydroindol- -yl)(substituted-phenyl)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.