YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
3H-Indoleの研究(第2報)Acyl Chloride付加体の転位反応 その1
高山 和男原野 一誠田口 胤三
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1974 年 94 巻 5 号 p. 540-547

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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 C27H25ON2Cl (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.

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