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

Article abstract of DOI:10.13005/ojc/290452

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.

Full text of DOI:10.13005/ojc/290452

ISSN: 0970-020 X
CODEN: OJCHEG
2013, Vol. 29, No. (4):
Pg. 1647-1650
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Synthesis and Antimicrobial Activity of 2-R 5-oxo 5-H
6-carbohydrazin 7-phenyl 1,3,4-thiadiazolo-[3,2-a] Pyrimidine
REZA MORADIVALIKBONI1*,
YULDASHBOY HOZHIBOEVY1 and ZABIALAH HEIDARNEZHAD2
1V.I.Nikitin Institute of Chemistry Academy of Sciences of the Republic of Tajikistan.
2Department of Chemistry,Andimeshk Branch, Islamic Azad University, Andimeshk , Iran
*Corresponding author E-mail: rmoradi02@yahoo.com
http://dx.doi.org/10.13005/ojc/290452
(Received: August 25, 2013; Accepted: October 19, 2013)
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.
Key words: Pyrimidine, Hydrazine, Synthesis, IR- spectroscopy, 13CNMR.
INTRODUCTION
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.
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]
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
moleculesmakesitpossibletosynthesizeheterocyclic
pyrido [3,2 , e]pyrimidines 10
.
Thioamides are mostly involved in
systems with various functional groups16,17
.
reactions related to the nucleophilic activity of these

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MORADIVALIKBONI et al., Orient. J. Chem., Vol. 29(4), 1647-1650 (2013)
Synthesis 2-R 5-oxo 5-H 6 -carbohydrazin
7-phenyl 1,3,4-thiadiazolo-[3,2-a]
RESULT AND DISCUSSION
Pyrimidineis carried out int wo stages.
At first, we have tried synthes is of 2- R
The first step we have synthesized 2-R5-oxo5-H6- 5-oxo 5-H 6-carbohydrazin 7-phenyl -1,3,4-
EthylCarboxilate7-phenyl [1,3,4]thiadiazolo[3,2,-a] thiadiazolo [3,2-a] pyrimidine with use 2-R 5-oxo
pyrimidine with Use from 2- R 5-amino 1,3,4- 5-H 6-ethylcarboxylate 7-phenyl 1 ,3,4-thiadiazolo
thiadiazole and ethyl 2- formyl 3- okco 3- phenyl
propanoate (Figure 1).
[3,2-a] pyrimidine andhydrazine in variousAlcohol.
But it looks better in the alcohols with less carbon
and hydrogen .Such as methanol or ethanol.
The Next Step we have synthesized
2-R 5-oxo 5-H 6 -carbohydrazin 7-phenyl 1,3,4-
To show the generality and applicability of
thiadiazolo-[3,2-a] pyrimidine from 2-R5-oxo5-H6- this procedure, we treated a wide variety of 2- R
EthylCarboxilate7-phenyl [1,3,4]thiadiazolo[3,2,-a] 5-oxo 5-H 6-ethylcarboxylate 7-phenyl 1 ,3,4-
pyrimidineand hydrazine in present solvent alcohol thiadiazolo [3,2-a] pyrimidine and hydrazine in the
ethanol (Figure 2).
presence of alcohol ethanol at 78°C and obtained the
Table 1: Synthes is 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
Entry
Thiadiazol
hydrazine
Product
Time(h) Yieldb(%)
O
O
O
CONHNH2
Ph
N
N
N
N
Et
Et
H
S
N
O
H
S
N
Ph
1
2
3
NH2NH2
NH2NH2
NH2NH2
6
5
5
90
87
90
O
O
N
CONHNH2
Ph
N
N
N
N
H3C
S
Ph
O
H3C
S
N
O
O
CONHNH2
Ph
N
N
N
N
Et
Ph
S
N
Ph
S
N
Ph
O
O
N
O
CONHNH2
Ph
N
N
Et
N
N
Ph
Ph
S
Ph
S
N
4
5
NH2NH2
NH2NH2
6
7
92
85
O
O
O
CONHNH2
Ph
N
N
N
N
Et
S
N
Ph
Br
Br
S
N
a Reactions were carried out with 2- R 5-oxo 5-H 6-ethylcarboxylate 7-phenyl 1 ,3,4- thiadiazolo [3,2-a] pyrimidine and hydrazine
b Yields refer to isolated pure products

MORADIVALIKBONI et al., Orient. J. Chem., Vol. 29(4), 1647-1650 (2013)
1649
O
O
C
COOEt
COOEt
Ph
N
N
N
N
Toluene
O
C
C
+
R
S
N
S
R
NH2
(1)
(2)
(3)
R:( H, CH3, Ph- , PhCH2-, Br)
Fig. 1: Synthes is of 2-R7-phenyl 6- ethylcarboxylate 5-oxo 5-H 1,3,4-thiadiazolo [3,2- a]pyrimidine
O
N
O
N
COOEt
CONHNH2
Ph
N
N
N
N
C2H5OH
Solvent
NH2NH2
(4)
+
R
S
Ph
R
S
(5)
(3)
R:( H, CH3, Ph- , PhCH2-, Br)
Fig. 2: Synthes is of 2- R 5-oxo 5-H 6-carbohydrazin7-phenyl -1,3,4-thiadiazolo [3,2-a]pyrimidine
desirable products in good to excellent yields (Table 2-H 5-oxo 5-H 6-carbohydrazin 7-phenyl -1,3,4-
1).
thiadiazolo [3,2-a] pyrimidine:1H NMR (400 MHz,
CDCl3, d 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, d ppm):118 (C), 126,4 (CH) , 126,4
EXPERIMENTAL
A mixture of 2-R 5-oxo 5-H 6-ethylcarboxylate (CH) ,128(CH), 128.7(CH), 128.7(CH), 136.9(C),140
7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine (1 .3(CH),162,1(C), 163 (C), 165.9(C ), 168(C).
mmol),hydrazine (1 mmol) was stirred magnetically at
78oC and the progress of the reaction was monitored CONCLUSIONS
by thin-layer chromatography (TLC). The reaction
in the various alcohol have been employed
mixture was filtered .In all the cases, the product as a mild and highly efficient solvent system for
obtained after the usual work up gave satisfactory the convenient preparation of 2- R 5-oxo 5-H
spectral data18-19
.
6-carbohydrazin 7-phenyl -1,3,4-thiadiazolo [3,2-a]
pyrimidine in excellent yields from 2- R 5-oxo 5-H
For example, 2-CH3 5-oxo 5-H 6-ethylcarboxylate 7-phenyl 1 ,3,4- thiadiazolo
6-ethylcarboxylate 7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine and hydrazine. The advantages
[3,2-a] pyrimidine (1 mmol-0.314gr),hydrazine (1 include low cost, mild reaction conditions and
mmol- 0.032gr) reated to gether in alcohol ethanol reactions carried out at room temperature with
at 78 oC.And the product is obtained in 87%yield. excellent yields.
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