Organizing co mmittee

 
 

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Poster presentation 
226 
HETEROCYCLIZATION OF 2-ALKYLTHIO-1,3,4-
THIADIAZOLE-5-PHENYLTHIOUREAS WITH MALONIC ACID 
 
T.T. Toshmurodov, A.A. Ziyaev, К.К. Turgunov 
 
S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of 
the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170, Tashkent, Uzbekistan 
e-mail: [e-mail] 
 
In our previous work [1,2], we reported the synthesis of several new 2-alkylthio-1,3,4-
thiadiazole-5-phenylthiourea derivatives. B
ased on these compounds, we studied the 
reaction of 2-butylthio-1,3,4-thiadiazole-5-phenylthiocarbamate (
1
) with malonic acid in 
order to synthesize new biologically active biheterocyclic compounds containing 3-phenyl-
2-thioxodihydropyrimidine-4,6(1H,5H)-dione fragment. The result of the reaction showed, 
the 
expected 
product 
- 
1-(5-(butylthio)-1,3,4-thiadiazol-2-yl)-3-phenyl-2-
thioxodihydropyrimidin-4,6(1H,5H)-dione (
3
) was not obtained, conversely, a new 
compound based on condensed 1,3,4-thiadiazolopyrimidine heterocycle - 2-(butylthio)-5-
oxo-5H-[1,3,4]-thiadiazolo[3,2-a]pyrimidine-7-ylacetate (
2
) was obtained in good yield.
For the reaction, equal amounts of reagent 
1
, acetyl chloride and malonic acid were 
taken, and dry was benzene used as solvents. The reactions were carried out at the boiling 
temperatures of the solvent for 8 and 3 hours respectively. In the experiment in benzene, no 
product was obtained, but in the reaction in acetyl chloride, compound 
2
was in successfully 
synthesized in good yield (73%). The structure of the new compound was proved by 
spectral methods (
1
H- and 
13
C-NMR, mass spectrum) and XRD method (Fig. 1) and the 
mechanism of product formation was proposed. 
Figure 1. Structure of