Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 1, pp. 81−84.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © V.M. Farzaliev, M.T. Abbasova, G.E. Gamidova, Ya.M. Kerimova, G.B. Babaeva, L.R. Safarova, 2012, published in Zhurnal
Prikladnoi Khimii, 2012, Vol. 85, No. 1, pp. 85−88.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis and Antimicrobial Properties
V. M. Farzaliev, M. T. Abbasova, G. E. Gamidova, Ya. M. Kerimova,
G. B. Babaeva, and L. R. Safarova
Kuliev Institute of Chemistry of Additives, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received August 30, 2010
Abstract—The possibility of synthesis of 3-(β-hydroxyethyl)-1,3-oxazolidin and its substituted derivatives at
position 2 by the condensation-heterocyclization of diethanolamine with certain aldehydes and ketones was
examined. The structure of the compounds was identiﬁ ed by NMR spectroscopy. We investigated antimicrobial
properties of the synthesized compounds against microorganisms that affect the lube oil M-11 and found
a dependence of the antimicrobial properties on the nature of the substituent at position 2 of oxazolidin heterocycle.
It is known that most of the currently used petroleum
products during storage, transportation, and operation
is affected by microorganisms. Microbial processes
occurring lead to a deterioration of physical-chemical,
operational, and hygienic properties of petroleum prod-
ucts, resulting in reduced service life, and materials and
constructions being in contact with petroleum products
are subjected to corrosion .
The most efficient way to protect the petroleum
products from microbial destruction is chemical method:
introduction in their composition of special antimicrobial
Since many biologically active compounds contain
structural fragments of N–C–O, N–C–N, and N–C–S,
compounds with these fragments in their structure were
obtained prior to synthesize new substances which are
promising as antimicrobial additives for mineral oils.
Thus, the condensation-heterocyclization of alkanol
amines  (or alkylene diamines ) was developed
with formaldehyde and hydroxyl-containing compounds
derived from N-alkoxymethyl derivatives of 1,3-dihet-
erocycloalkanes (1,3-oxazines, 1,3-oxazolidins, 1,3-per-
hydropyrimidines, 1,3-imidazolidines). Microbiological
tests have shown high efﬁ ciency and broad spectrum of
antimicrobial action of these compounds to the microor-
ganisms which affect petroleum products.
Therefore, synthesis of novel 1,3-diheterocycloalkane
derivatives deserved attention as possible antimicrobial
agent with respect to petroleum products.
In the study we considered diethanolamine condensa-
tion with certain aldehydes and ketones which resulted
in 1,3-oxazolidin derivatives substituted at position 3 by
β-hydroxyl group and at position 2 by alkyl or aryl group.
Formaldehyde (in the form of paraform), benzalde-
hyde, and its F, Cl, OH-substituted derivatives were used
as aldehydes. Methylpropyl- and methylhexylketones
were applied as ketones.
Diethanolamine condensation with aldehydes and
ketones was carried out according to the known technique
 at a molar ratio of initials reagents 1 : 1 by heating in
benzene or toluene which was taken according to boiling
point of the initial aldehyde or ketone, with azeotropic
distillation of a reaction water into Dean–Stark trap. The
reaction end was determined by completion of water
release. Physical chemical constants and data of
spectra of the products are listed in the table. In addition,
for clarity we recorded
C NMR spectra of compounds
II and III.
Diethanolamine condensation with formaldehyde
(in the form of paraform) at the 1 : 1 ratio of the initial
reagents proceeds readily. 3-(β-Hydroxyethyl)-1,3-
oxazolidin with 90% yield was obtained after distilling