Yasuyuki Yoshitake

Reaction of 1-Acyl- and Aroyl-2-hydroxy-3,3-dimethylindolines with Arylamines Catalyzed by BF3・Etherate. Formation of Dihydroindolo[1,2-c]quinazoline

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.

Cycloaddition reaction of 4-oxo-4H-pyrazole 1,2-dioxides with epoxynaphthalene. X-ray analysis of the cycloadduct and some comments on cycloaddition behavior

The crystal structure of the cycloadduct of 2,5-bis(methoxy- carbonyl)-4-exo-4H-pyrazole 1,2-dioxide with epoxynaphthalene was elucidated. The result indicates that the cycloadduct resulted from the direct 1,3-dipolar cycloaddition