3H-Indoleの研究(第2報)Acyl Chloride付加体の転位反応その1

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When 1-(P-chlorobenzoyl)-3,3-dimethylindolin-2-ylpyridinium chloride (IIa) was pyrolyzed in pyridine, 1-(p-chlorobenzoyl)-2,3-dimethylindole (Va) was obtained together with a pair of geometrical isomers consisting of C_<27>H_<25>ON_2Cl (M^+428). The isomers were characterized as 5-(p-chlorobenzoyl)-5a, 5b, 6,11a-tetrahydro-5a, 6,6,11a-tetramethylindolo-[1,2 : 1', 2']azetidino[3,4-b]indole (IIIa-1,2) on the basis of mass and nuclear magnetic resonance spectral data. An additional structual proof for IIIa-1,2 was provided by the formation of 5-(p-chlorobenzyl)-5a, 5b, 6,11a-tetrahydro-5a, 6,6,11a-tetramethylindolo-[1,2 : 1', 2']azetidino-[3,4-b]indole (VI), 2,3-dimethylindole (VII), and 3,3-dimethylindoline (VIII) by the reduction of III with lithium aluminum hydride. 3-Methyl-3-ethyl (XIIIa) and 3,3-diphenyl (XIIIc) analogs of IIa showed the same behavior as IIa by pyrolysis.
公益社団法人日本薬学会の論文
1974-05-25