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Indolo[3,3a,4‐ gh ]chinoline und 10a, 6a‐Iminopropano‐indolo‐[3,3a,4‐ gh ]chinoline. Stereospezifische Synthesen und Umlagerungen. Teil II. 9. Mitteilung über synthetische Indolverbindungen
Author(s) -
Stoll André P.,
Niklaus P.,
Troxler F.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540728
Subject(s) - chemistry , benzylamine , stereochemistry , quinoline , ring (chemistry) , lactam , protonation , indole test , bicyclic molecule , medicinal chemistry , organic chemistry , ion
Alkaline hydrolysis of 1‐benzyl‐4, 4‐dicyanoethyl‐5‐oxo‐1,3,4,5‐tetrahydro‐benzo‐[ cd ]indole under controlled conditions leads to 4‐benzyl‐4,6,7,8‐tetrahydro‐10a, 6a‐iminopropanoindolo[3,3a,4‐ gh ]quinoline‐9(10 H ),12‐dione ( 2a ), the first representative of such a ring system. Alkylation of this di‐lactam affords the N‐monoalkyl ( 2b ), the N, N'‐dialkyl ( 3 ), and the N, O‐dialkyl ( 4 ) derivatives according to the conditions employed. Treatment of compounds such as 2 with sodium in liquid ammonia results in the opening of one of the lactam rings by a stereoelectronically controlled reductive cleavage of the benzylamine bond; subsequent protonation proceeds stereospecifically to give trans ‐octahydroindolo[3,3a, 4‐gh]quinolines (viz. 5 ). The NMR. spectra and the mechanism of the reductive ring opening are discussed.