Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 7, pp. 1255−1262.
Pleiades Publishing, Ltd., 2009.
Original Russian Text
Kh.M. Alimardanov, O.A. Sadygov, E.T. Suleimanova, N.A. Dzhafarova, M.Ya. Abdullaeva, N.R. Babaev, 2009, published in
Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 7, pp. 1159−1166.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis and Examination of Antimicrobial Properties
of Aminomethylated Derivatives
of Alicyclic Diols
Kh. M. Alimardanov, O. A. Sadygov, E. T. Suleimanova, N. A. Dzhafarova,
M. Ya. Abdullaeva, and N. R. Babaev
Institute of the Petrochemical Processes, Azerbaijanian Academy of Sciences, Baku, Azerbaijan
Received December 3, 2008
Abstract—Synthesis of C
alicyclic diols was studied by a catalytic oxidation of cyclohexene, norbornene and
their methyl derivatives in the presence of heterogenized molybdenum-containing catalysts. By a triple condensation
of the diols with formaldehyde and secondary amines a synthesis of their aminomethylated derivatives with
various substituents at nitrogen atom was examined. Antimicrobial properties of the synthesized amino alcohols
in M-10 oil as additives with fungicidal and bactericidal activities were studied.
Alicyclic amino alcohols containing alkyl-, aryl-, and
heterocyclic substituents at nitrogen atom are promising
intermediates of organic and petroleum synthesis whose
structural features determine their rich functional
capacity as monomers and biologically active substances
employed in pharmaceuticals of various functions [1–3].
These compounds are of interest due to the presence of
similar structural moieties in composition of many natural
biologically active substances [4, 5].
Unlike amino alcohols of aliphatic and aromatic series
[6–8] similar derivatives of alicyclic series [9, 10] attract
signiﬁ cantly smaller attention. Data on the synthesis
of aminomethylene derivatives from cyclohexane and
norbornane diols, and on the investigation of their
biological properties are practically lacking.
It is known that the simultaneous presence in a
molecule of amino- and hydrosubstituents imparts to
them antioxidation and antimicrobial properties .
Nowadays when machines and mechanisms are improved
a protection of applied oils, fuels, and composed polymeric
and other materials from biodamages is actual .
Our paper is aimed at a synthesis of N-substituentd
amino alcohols of cyclohexane and norbornane series
by induced oxidation of the corresponding cyclooleﬁ ns
with hydrogen peroxide in the presence of acetic acid
and heterogenic catalysts obtained on the basis of
bentonite, kaolin, and halides or oxyhalides of metalls
of VI–VIII groups of the periodic system, followed
by aminomethylation of the reaction products without
previous separation of oxidate, and also at a research
of the antimicrobial properties of the synthesized
Starting cyclohexene and 1-methylcyclohexene were
prepared by cyclohexanol and 3-methylcyclohexanol-1
dehydration at 220–250°С on γ-Al
2-ene and its 5-methyl derivative we synthesized by
condensation of cyclopentadiene with ethylene and
propylene with the aid of a known technique .
Samples of catalysts we impregnated with a mixture
of bentonite, kaolin, and aqueous or alcoholic solutions
by their carbonization in 4-vinylcyclohexene ﬂ ow at
500–550°С in the course of 4 h.