G. Butov, V. Mokhov
Apr 23, 2014
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0
Influential Citations
6
Citations
Journal
Russian Journal of Organic Chemistry
Abstract
Among biologically active adamantane derivatives, a particular place is occupied by those containing nitrogen heterocycles, including saturated rings with one or two nitrogen atoms and morpholine ring, where the adamantyl radical is attached to the nitrogen atom. Derivatives of 1and 2-aminoadamantane in which the amino nitrogen atom is a part of heterocyclic fragment attract interest as antiviral and anti-Parkinson drugs [1, 2]. The known methods of synthesis of such compounds are based on adamantylation of piperidine, piperazine, or morpholine [3] with haloadamantanes or cyclization of difunctional amines, N,N-bis(2-hydroxyor 2-chloroethyl)adamantan-1-amines. In the first case, the reactions require high temperature, long reaction time, and the use of excess heterocyclic amine to bind liberated hydrogen halide and are accompanied by side Grob fragmentation, tarring, and other undesirable processes. The synthesis from 1-aminoadamantane [4] is multistep, and the yield of the target products is low.