A series of 1-substituted 2,3-polymethyleneindoles was prepared and examined for central nervous system activity. A number of these compounds wrere found to be active as antidepressants. The required 2,3-polymethyleneindoles were prepared by suitable modifications of the Fischer indole synthesis from arylhydrazines and alicyclic ketones. These were converted to N-substituted derivatives by various methods.
4,4‐Dialkyl‐4‐germacyclohexanones have been synthesized and their reactions studied. The diethyl ketone has been converted into N‐(‐dimethylaminopropyl)‐2 aza‐8,8‐diethyl‐8‐germaspiro[4.5]decane (16). The biological properties of 16 have been examined in some detail. The reactions of this new ketone with some other reagents are reported.
Series of iV-alkyl and N-dialkylaminoalkyl-S-azabicyclo[3.2.0]heptane-2,4-dione have been prepared from the reaction of the appropriate primary amines and cis-1,2-cyclobutane dicarboxylic anhydride and cyclization of the resulting amic acids. The A-alkyl and iV-dialkylammoalkyl imides thus obtained were reduced to the corresponding iV-alkyl and iV-dialkylaminoalkyl-3-azabicyck> [3.2.0 jheptanes with lithium aluminum hydride. These bases were characterized as hydrochlorides, mono-and bis-methiodides and picrates. The bis-quaternary salts derived from the 3-azabicyclo[3.2.0]heptane nucleus with a dialkylaminoalkyl side chain possessed hypotensive activity in cannulated dogs. The most favorable structure was one in which the number of methylene carbon atoms between the onium centers was 2 or 3 and the introduced quaternary group was a short chain alkyl group such as methyl or ethyl.
During the past several years we have prepared a relatively large number of cyclic bases which have been screened for hypotensive activity as hydrochlorides and quaternary salts. We have found with the majority of compounds prepared in the several series studied so far that the bases could be prepared conveniently and in good yields by the reduction of the corresponding imides with lithium aluminum hydride. As a result of this continued study we have prepared a large number of N-alkyl-and N-dialkyl-aminoalkyl imides as intermediates in the synthesis of the desired bases.A survey of the literature concerning the particular series of imides that we wish to report here revealed that one t o several members had been reported in each series but that in many cases the physical data were scanty. Also, the previously reported imides, prepared by a variety of methods, are scattered in many sources in the literature. We have prepared the present four series of N-alkyl imides, in amounts varying from 4 to 90 grams, by a single general method and have assembled complete data on boiling points, melting points, densities, and refractive indices.In the present article we wish to report the N-alkyl succinimides from butyl through dodecyl (I) ; the N-alkyl-cis-A4-tetrahydrophthalimides, methyl through dodecyl (11) ; the N-alkyl-cis-3, 6-endomethylene-A4-tetrahydrophthalimides, butyl through dodecyl (111) ; and the N-alkyl hexahydrophthalimides, methyl through dodecyl (IV). 0 0 0 0
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