SYNTHESIS OF HETEROCYCLES FROM 1,5-DIKETONES: 3.* ALICYCLIC 1,5-DIKETONES IN REACTION WITH PHENYLHYDRAZINE

Article abstract of DOI:10.1007/BF00515421

8-R-7aH-5,6,7,8,9,10,11,12-Octahydroindolo<3.2.1-d,e>acridines, 1,2,3,4-tetrahydrocarbazole,9-R-sym-octahydroacridines, and 9-R,10-phenyl-sym-octahydroacridinium salts are formed by the action of phenyl-hydrazine on alkylidene-2,2'-dicyclohexanine or the corresponding 8-R-tricyclo(7.3.1.0^2,7)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'-dimethyltetrahydropyran-4'-on-5'-ylmethyl)-4aH-1,2,3,4-tetrahydrocarbazole by the action of ammonia.