Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 3, pp. 404−409.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © Yu.V. Popov, V.M. Mokhov, N.A. Tankabekyan, 2013, published in Zhurnal Prikladnoi Khimii, 2013, Vol. 86, No. 3, pp. 435−440.
AND INDUSTRIAL ORGANIC CHEMISTRY
Condensation of Adamantanone
with Methylene-Active Compounds
Yu. V. Popov, V. M. Mokhov, and N. A. Tankabekyan
Volgograd State Technical University, Volgograd, Russia
Received July 12, 2012
Abstract—A convenient method was developed for the preparation of potentially bioactive substances with
2-adamantyl radical and of intermediates for their synthesis. Condensation of adamantanone with methylene-active
compounds was performed, and the reaction features were determined.
Chemistry of polyhedrane compounds, especially
of those containing adamantyl radical, attracts much
researchers’ attention. It is known that a wide series
of adamantane derivatives exhibit various kinds of
biological activity ; some of them are included in the
catalog of the Ministry of Public Health of the Russian
Federation and are produced under various trade names.
In particular, nitrogen-containing adamantane derivatives
exhibit biological activity and are used as antiviral
drugs (Remantadine, Midantane, Adapromine, etc.).
The adamantane derivatives bearing a substituent at
the methylene carbon atom (2-position) are often more
promising from the viewpoint of biological activity
than the derivatives substituted at the methine atom
(1-position) . Thus, search for routes to 2-substituted
adamantane derivatives is a topical problem.
The goal of this work was the development of
convenient methods for preparing these compounds,
based on condensation of adamantanone with various CH
acids, and study of further transformations of the products
obtained into amine.
To choose the structure of the target products
and plan the routes of their synthesis, the probable
biological activity of a series of 2-substituted adamantane
derivatives was predicted. The development of
procedures for preparing 2-(2-amino)ethyladamantane,
which exhibits the properties of dopamine release
stimulant and ligase inhibitor, was shown to be topical.
2-(Adamantylidenemethyl)quinoline can exhibit the
same properties, acting, in particular, as taurine inhibitor.
may also be of considerable interest.
The anticipated practical significance of these
compounds was conﬁ rmed by Zoidis et al. , who
studied the synthesis and biological activity of 1- and
2-substituted amino derivatives of adamantane. They
showed, in particular, that adamantane-containing
derivatives of pyrrolidine, oxazolone, pyrazolone,
pyrazolinethione, and cyclopentylamine exhibit antiviral
activity toward inﬂ uenza A viruses and kill parasitic
microorganisms trypanosomes. Adamantane-substituted
pyrrolidine exhibits 4 times higher antiviral activity than
Amantadine and Remantadine do, and toward African
blood trypanosomes the corresponding substituted
oxazolone is 3 times more active than Remantadine and
50 times more active than Amantadine .
Therefore, it is topical to search for procedures for
adamantane functionalization with the formation of a
new C–C bond in the 2-position of the adamantyl group.
It is known that condensation of adamantanone
with CH acids is a convenient method for introducing
a side carbon into 2-position of the adamantyl group.