ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19710540728
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