Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 9, pp. 1387−1394.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © Yu.V. Popov, V.M. Mokhov, N.A. Tankabekyan, O.Yu. Safronova, 2012, published in Zhurnal Prikladnoi Khimii, 2012, Vol. 85, No. 9,
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis of 2-Amino-2-cyanoadamantane
and Its Derivatives
Yu. V. Popov, V. M. Mokhov, N. A. Tankabekyan, and O. Yu. Safronova
Volgograd State Technical University, Volgograd, Russia
Received January 12, 2012
Abstract—Synthetic routes to new amino nitriles with the functional groups at the 2-position of the adamantane
core, based on reactions of adamantanonimines with acetone cyanohydrin or of adamantanone cyanohydrin with
aliphatic amines, are considered. The products can be used for preparing new biologically active substances,
unsymmetrical adamantyl-containing diamines or amino acids.
Many adamantane derivatives exhibit diverse kinds
of biological activity. Some of these compounds are used
as drugs . Already the early studies on the synthesis of
2-alkyl(aryl)aminoadamantanes [2, 3] showed that these
compounds have a broad spectrum of pharmacological
activity. Studies in the ﬁ eld of synthesis and activity
of 2-substituted adamantanes are being continued .
Recent studies of hydroxyaminoalkyladamantanes,
structural analogs of Remandatin, also substituted at
the 2-position of the adamantane core, revealed high
antiviral activity and other kinds of activity of these
compounds [5, 6].
Among 2-substituted adamantane derivatives, Bro-
mantane [2-(4-bromophenylamino)adamantane hydro-
chloride] is well known . It seems promising to modi-
fy the structure of this compound by introducing into the
2-position of the adamantane core one more substituent,
in particular, an aminomethyl group, which can alter the
existing biological activity or give rise to new kinds of
biological activity. Published data on synthetic routes to
compounds of this structure are lacking.
The goal of this study was to develop convenient
procedures for preparing adamantane derivatives.
The starting compounds for preparing aminomethyl
derivatives are the corresponding adamantyl-containing
α-amino nitriles. Traditional methods for preparing
α-amino nitriles consist in the reaction of a carbonyl
compound with an amine and hydrogen cyanide, with
alkali metal cyanides  or silyl cyanides  used
as a source of HCN. The apparent drawback of these
methods is the use of very toxic or difﬁ cultly available
In this study we developed a procedure for preparing
adamantyl-containing amino nitriles by the reactions
of 2-cyano-2-hydroxyadamantane (adamantanone
cyanohydrin) with ammonia, primary and secondary
amines, and hydrazines. Technical-grade ethanol can be
used as solvent.
The starting 2-cyano-2-hydroxyadamantane II was