TECHNOLOGY OF ORGANIC
AND INORGANIC CHEMISTRY
Russian Journal of Applied Chemistry, 2008, Vol. 81, No. 3, pp. 513−515. © Pleiades Publishing, Ltd., 2008.
Original Russian Text © O.V. Platonova, S.B. Volkova, S.A. Malin, E.A. Veretennikov, B.M. Laskin, A.S. Malin, 2008, published in Khimicheskaya Promyshlen-
nost’, 2008, Vol. 85, No. 1, pp. 1−4.
Synthesis of New Substituted Thiazoles
Containing Aminooxadiazole Ring
O. V. Platonova, S. B. Volkova, S. A. Malin, E. A. Veretennikov, B. M. Laskin, and A. S. Malin
Russian Scientiﬁ c Center “Applied Chemistry,” St. Petersburg, Russia
Received February 12, 2007
Abstract—Synthesis of biheterocyclic thiazole–amonooxadiazoles, the potential biologically active compounds
is developed. Regularities of transformations and physico-chemical characteristics of intermediates and ﬁ nal
compounds are revealed.
The heterocycles of thiazole series are known to pos-
sess biological activity; some representatives of this class
compounds are well-known medicine preparations [1,
2]. Compounds containing simultaneously thiazole and
aminooxadiazole fragments merit special mentioning.
Synthesis of these potentially biologically active com-
pounds practically has not been described. We developed
a few-step procedure for the synthesis of thiazole–ami-
nooxadiazoles and studied conditions of the process and
its technological parameters.
Substituted thiazoles IIa–IId were prepared by reaction
of chloroacetoacetic esters prepared in correspondence
with the procedure in  with thioacetamide in alcohol
medium (like Hanch reaction [4, 5]) at 80–90°С, duration
period 7–12 h, yield up to 75–80%.
Compounds IIa–IId are crystalline substances melting
in the temperature range from 56 to 65°С.
Note that at the synthesis of compounds IIa–IIc the
process duration increases for the series of substituents
а to c, probably in connection with steric properties of
these substituents. The process duration for compound
IId increases probably due to strong electromeric ef-
fect of conjugated system that includes phenyl group.
Introduction of triethylamine to the reaction zone allows
accelerate the process considerably and increase yield of
compound IId to 75%.
The process conditions for the synthesis of the thiazoles
and some of their characteristics are listed in Table 1.
Synthesis of corresponding hydrazines IIIa–IIId has
been poorly illuminated in literature. We prepared hydra-