Reaction of alkali-metal hypohalites with stereoisomeric 2-methyl-1-alkyl-2-methyl-4-ethynyldecahydro-4-quinolols |
| |
Authors: | A. A. Akhrem L. I. Ukhova G. V. Bludova T. M. Tsvetkova G. I. Trus N. I. Garbuz L. P. Solovei |
| |
Affiliation: | (1) Institute of Bioorganic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk |
| |
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 CC 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.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 98–103, January, 1976. |
| |
Keywords: | |
本文献已被 SpringerLink 等数据库收录! |
|