ISSN:
1573-8353
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract 8-R-7aH-5,6,7,8,9,10,11,12-Octahydroindolo[3.2.1-d,e]acridines, 1,2,3,4-tetra-hydrocarbazole, 9-R-sym-octahydroacridines, and 9-R,10-phenyl-sym-octahydroacridinium salts are formed by the action of phenyl-hydrazine on alkylidene-2,2′-dicyclohexanone or the corresponding 8-R-tricyclo(7.3.1.02,7)tridecan-2-ol-13-ones in an acid medium. Postulations were made for the paths of formation of these compounds. 2,2-Dimethyl-3-oxa-4a-(2′,2′-dimethyltetrahydropyran-4′-on-5′yl-methyl)-4aH-1, 2,3,4-tetrahydrocarbazole, 3,3,14,14-tetramethyl-2-oxa-5a,10b-(methanoxyisobutane)-1,2,3,4,5a,10b,11,11a-octahydroquinindoline, 2,2-dimethyl-3-oxa-1,2,3,4-tetrahydrocarbazole and 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydroacridine were obtained by the reaction of methylene-3,3′-di(6,6-dimethyltetrahydropyran-4-one) with phenylhydrazine in acetic acid. The quinindoline structure was confirmed by the synthesis of this compound from 2,2-dimethyl-3-oxa-4a-(2′,2′-dimethyl-tetrahydropyran-4′-on-5′-ylmethyl)-4aH-1,2,3,4-tetrahydrocarbazole by the action of ammonia.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00515421
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