Abstract
Isomeric 1-alkyl-2-methyl-4- (haloethynyl) decahydro-4-quinolols were synthesized by reaction of the individual stereoisomers of 1-alkyl-2-methyl-4-ethynyl-decahydro-4-quinolols with alkali solutions of potassium hypochlorite and hypobromite. 1-Chloro-2-methyl-4-ethynyl decahydro-4-quinolols are formed by the action of an alkaline solution of potassium hypochlorite on isomeric 2-methyl-4-ethynyldecahydro-4-quinolols. Hydrogenolysis of the carbon-halogen bond accompanied by hydrogenation of the C≡C bond was observed under conditions of catalytic hydrogenation of 1,2-dimethy1-4-(haloethynyl) decahydro-4-quinolols. Primarily hydrogenolysis of the nitrogen-halogen bond and subsequent reduction of the acetylenic bond occur in the hydrogenation of 1-chloro-2-methyl-4-ethynyldecahydro-4-quinolols. Replacement of chlorine by hydrogen and subsequent alkylation of the resulting secondary amine and formation of the hydrochlorides of the corresponding N-methyl-substituted acetylenic alcohols occur in the reaction of the chloramines with a mixture of formaldehyde and formic acid.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 98–103, January, 1976.
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Akhrem, A.A., Ukhova, L.I., Bludova, G.V. et al. Reaction of alkali-metal hypohalites with stereoisomeric 2-methyl-1-alkyl-2-methyl-4-ethynyldecahydro-4-quinolols. Chem Heterocycl Compd 12, 90–95 (1976). https://doi.org/10.1007/BF00473921
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DOI: https://doi.org/10.1007/BF00473921