REACTION OF 1-ACYL AND AROYL-2-HYDROXY-3,3-DIMETHYL-INDOLINES WITH ARYLAMINES CATALYZED BY BF3·ETHERATE.FORMATION OF DIHYDROINDOLO[1,2-c]QUINAZOLINE

摘要

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-l-yl]ethanone.The reactions of several (2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-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.