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

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(10H),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.     

5,6-Dihydro-4h-imidazole[4,5,1-i,j]quinoline derivatives

2-Alkyl(dialkyl)amino derivatives of I and their respective cyclic ammonium salts were obtained by reaction of the 2-chloro derivative of 5,6-dihydro-4H-imidazole [4,5,1-i,j ]quinoline (I) and its methiodide with amines. The eycloammonium salt was converted into 2-amino(alkylimino)-l,2-dihydro derivatives of 5. Methoxy- and methyl-substituted I readily formed 2-amino derivatives by reaction with sodium amide. Comparison of the UV spectra of the 2-amino derivative of I and its fixed tautomeric form indicates that the 2-amino derivative of I exists primarily in the amino form in dioxane and CC14.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1410–1413, October, 1970.     

Steroid sapogenins of Smilax excelsa

Chemistry of Natural Compounds -