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Synthesis and Antimicrobial Activity of 2-R 5-oxo 5-H 6 -carbohydrazin 7-phenyl 1,3,4-thiadiazolo-[3,2-a] pyrimidine

Volume 29, Number 4

Reza Moradivalikboni1*, Yuldashboy Hozhiboevy1, Zabialah Heidarnezhad2

1V.I.Nikitin Institute of Chemistry Academy of Sciences of the Republic of Tajikistan 2Department of Chemistry, Islamic Azad University, Andimeshk , Iran

DOI : http://dx.doi.org/10.13005/ojc/290452

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Article Published : 12 Dec 2013
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ABSTRACT:

The synthesis of 2-R 5-oxo  5-H  6 -carbohydrazin 7-phenyl  1,3,4-thiadiazolo-[3,2-a] pyrimidine is described. This compound exhibits a broad spectrum of antimicrobial action and can be useful in the search for new antimicrobial drugs. Reactions  of 2- R  5 - Oxo  5 - H  6- EthylCarboxilate 7 – phenyl   -1, 3,4 – Thiadiazolo-[3,2-a] pyrimidine   with hydrazine produce  2-R 5-oxo  5-H  6 – carbohydrazin 7-phenyl  1,3,4-thiadiazolo-[3,2-a] pyrimidine. The structures of the compounds obtained are set NMR, 13C, IR- spectroscopy.

KEYWORDS:

pyrimidine;Hydrazine;Synthesis;IR- spectroscopy;NMR;13C

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Moradivalikboni R, Hozhiboevy Y, Heidarnezhad Z. Synthesis and Antimicrobial Activity of 2-R 5-oxo 5-H 6 -carbohydrazin 7-phenyl 1,3,4-thiadiazolo-[3,2-a] pyrimidine. Orient J Chem 2013;29(4)

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Moradivalikboni R, Hozhiboevy Y, Heidarnezhad Z. Synthesis and Antimicrobial Activity of 2-R 5-oxo 5-H 6 -carbohydrazin 7-phenyl 1,3,4-thiadiazolo-[3,2-a] pyrimidine. Orient J Chem 2013;29(4). Available from: http://www.orientjchem.org/?p=1162

INTRODUCTION

1,3,4-thiadiazolo [3,2-a] pyrimidine system efficiently enhances the physiological activity of the molecule 1-3. This replacement occurs in the reactions of 1,3,4– thiadiazolo [3,2-a]pyrimidine derivatives with electrophiles4-5.Literature data on fused heterocycles with athiadiazolo [3,2-a] pyrimidine system anelated with an other ring are scarce.These include 1,3,4-thiadiazolo [3,2 -b] quinozalhaes,6-8 pyrazolol [3 ,4-e] 1 ,3,4-thiadiazolo [3,2 –alpyrimidines9 and 1,3,4-thiadiazolo [3 , 2-a] pyrido [3,2 , e]pyrimidines 10.

Thioamides are mostly involved  in reactions related to the nucleophilic activity of these compounds, where by sulfuror nitrogen atoms act as reactive centers. In particular, thioamides readily react with alkyl halogenides and alkyl sulfides with the formation of S-alkyl-isothiuronium salts11.

With a view to investigation of the reaction cability of 1,3,4-thiadiazolo-[3,2-a]pyrimidine derivatives and the search for new physiological compounds in this group, we have synthesized a series of thiuronium salts from various thioamides.

Derivatives of 1,3,4-thiadiazolo [3,2-a]pyrimidine are  potential biologically active substances,12-15.The introduction of  ketene dithioacetal fragments into the molecules makes it possible to synthesize heterocyclic systems with various functional groups 16,17.

Synthesis 2-R 5-oxo  5-H  6 -carbohydrazin 7-phenyl  1,3,4-thiadiazolo-[3,2-a] Pyrimidineis carried out int  wo stages.The first step we have synthesized 2-R5-oxo5-H6-EthylCarboxilate7-phenyl [1,3,4]thiadiazolo[3,2,-a]pyrimidine with Use from 2- R 5-amino  1,3,4- thiadiazole and ethyl 2- formyl 3- okco 3- phenyl propanoate (Figure 1).

 

 Fig. 1: synthes is of 2-R7-phenyl 6- ethylcarboxylate 5-oxo 5-H 1,3,4-thiadiazolo [3,2- a]pyrimidine Fig. 1: synthes is of 2-R7-phenyl 6- ethylcarboxylate 5-oxo 5-H 1,3,4-thiadiazolo [3,2- a]pyrimidine 
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The Next Step we have synthesized 2-R 5-oxo 5-H  6 -carbohydrazin  7-phenyl 1,3,4-thiadiazolo-[3,2-a] pyrimidine from 2-R5-oxo5-H6-EthylCarboxilate7-phenyl [1,3,4]thiadiazolo[3,2,-a]pyrimidineand  hydrazine in present  solvent alcohol ethanol (Figure 2).

 

Fig. 2:synthes is of 2- R 5-oxo 5-H 6-carbohydrazin7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine Fig.  2:synthes is of  2- R 5-oxo  5-H  6–carbohydrazin7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine

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RESULT AND DISCUSSION

At  first, we have tried synthes is of  2- R 5-oxo  5-H  6-carbohydrazin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine with use 2-R  5-oxo  5-H  6-ethylcarboxylate  7-phenyl  1 ,3,4-thiadiazolo [3,2-a] pyrimidine  andhydrazine in variousAlcohol. But it looks better in the alcohols with less carbon and hydrogen .Such as methanol or ethanol.

To show the generality and applicability of this procedure, we treated a wide variety of  2- R  5-oxo  5-H  6-ethylcarboxylate  7-phenyl  1 ,3,4- thiadiazolo [3,2-a] pyrimidine  and hydrazine  in the presence of alcohol ethanol at 78 oC and obtained the desirable products in good to excellent yields (Table 1).

 

 Table 1 Table 1: synthesis of  2- R 5-oxo  5-H  6-carbohydrazin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine with 2- R  5-oxo  5-H  6-ethylcarboxylate  7-phenyl  1 ,3,4- thiadiazolo [3,2-a] pyrimidine  and hydrazinea 

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EXPERIMENTAL

A mixture of  2-R  5-oxo  5-H  6-ethylcarboxylate  7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine (1 mmol),hydrazine (1 mmol) was stirred magnetically at 78oC and the progress of the reaction was monitored by thin-layer chromatography (TLC). The reaction mixture was filtered .In all the cases, the product obtained after the usual work up gave satisfactory spectral data.[18-19]

For example, 2-CH3  5-oxo  5-H  6-ethylcarboxylate  7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine (1 mmol-0.314gr),hydrazine (1 mmol- 0.032gr) reated to gether in alcohol ethanol at 78 oC.And the product is obtained in 87%yield. 2-H 5-oxo  5-H  6-carbohydrazin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine:1H NMR (400 MHz, CDCl3, δ ppm):4.35 (s, 2H, NH2) ;  7.14-7.30 (5H, Ph);

7.50 (S, H):9.85 (s, H, NH) –13C NMR (100 MHz, CDCl3, δ ppm):118 (C), 126,4 (CH) , 126,4 (CH) ,128(CH), 128.7(CH), 128.7(CH), 136.9(C),140 .3(CH),162,1(C), 163 (C), 165.9(C ), 168(C).

CONCLUSIONS

In the various alcohol have been employed  as a mild and highly efficient solvent system for the convenient preparation of 2- R 5-oxo  5-H  6-carbohydrazin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine in excellent yields from 2- R  5-oxo  5-H  6-ethylcarboxylate  7-phenyl  1 ,3,4- thiadiazolo [3,2-a] pyrimidine and hydrazine. The advantages include low cost, mild reaction conditions and reactions carried out at room temperature with excellent yields.

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