Reaction 2-R 5-oxo 5-H 6-ethylcarboxylate 7-phenyl-1,3,4-thiadiazolo-[3, 2-a] pyrimidine with amine

Article abstract of DOI:10.13005/ojc/300153

In this article presents Synthesis of 2-R5-oxo 5-H 6-Carboxamid 7-phenyl 1, 3, 4-thiadiazolo-[3, 2-a] pyrimidine through reaction of 2-Ft 5-Oxo 5-H 6-EthylCarboxilate 7-phenyl-1, 3, 4-Thiadiazolo-[3, 2-a] pyrimidine with amine. The structures of the compounds obtained are set NMR, ¹³C, IR-spectroscopy.

Full text of DOI:10.13005/ojc/300153

ISSN: 0970-020 X
CODEN: OJCHEG
2014, Vol. 30, No. (1):
Pg. 375-378
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Reaction 2-R 5-oxo 5-H 6-Ethylcarboxylate
7-phenyl-1,3,4-thiadiazolo- [3,2-a] pyrimidine with Amine
REZA MORADIVALIKBONI1*, ZABIALAH HEIDARNEZHAD2,FATEMEH HEYDARI2,
HESHMATOLLAHALINEZHAD1 and SAHAR MOHSENITAVAKOLI1
1Department of Chemistry, Mazandaran University, Babolsar, Iran.
2Department of Chemistry,Andimeshk Branch, Islamic Azad University, Andimeshk, Iran.
*Corresponding author E-mail: rmoradi02@yahoo.com
http://dx.doi.org/10.13005/ojc/300153
(Received: October 05, 2013; Accepted: November 21, 2013)
ABSTRACT
In this article presents Synthesis of 2-R5-oxo 5-H 6-Carboxamid 7-phenyl 1,3,4-thiadiazolo-
[3,2-a] pyrimidine through reaction of 2- R 5-Oxo 5-H 6- EthylCarboxilate 7- phenyl-1, 3,4-
Thiadiazolo-[3,2-a] pyrimidine with amine.The structures of the compounds obtained are set NMR,
13C, IR- spectroscopy.
Key words: NMR, IR- spectroscopy,13C ,pyrimidine and Thiadiazol.
INTRODUCTION
The introduction of a substituent at position
6 of the1,3,4-thiadiazolo [3,2-a] pyrimidine system
efficientlyenhances the physiological activity of the
oleculef8-10.This replacement occurs in the reactions
of 1,3,4 -thiadiazolo [3,2-a] pyrimidine derivatives
withelectrophiles11-15.In the present work, we studied
the possibilities of thesynthesis of various derivatives
of 1,3,4-thiadiazolo [3,2 -a] pyrimidine.
Condensed derivatives of 1,3,4-
thiadiazolo[3,2- a]pyrimidinewere reported to
possess a broadspectrum of biological activity1-4,
including antibacterial,antitumor, fungicidal, and
herbicidal properties. However,thiadiazoles and
their condensed analogs are still in sufficiently
studied.In continuation of the search for substances
possessing increased ability to permeate through
biologicalmembranes of various infectious species
5 – 7 and, in particular, for the new antibacterial drugs
in these homologousseries of compounds.
In First we hav synthesized 2-R5-oxo5-H6-
Ethyl Carboxilate7-phenyl [1,3,4] thiadiazolo [3,2,-
thiadiazole(1)andethyl 2- formyl 3- okco 3- phenyl
propanoate(2). (Figure 1)

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MORADIVALIKBONI et al., Orient. J. Chem., Vol. 30(1), 375-378 (2014)
And more2-R5-oxo5-H6-Ethyl Carboxilate 7-phenyl 1 ,3,4-thiadiazolo [3,2-a] pyrimidine and
7-phenyl [1,3,4]thiadiazolo[3,2,-a]pyrimidinereacted amin in variousAlcohol. The reaction performed
with amin(4) until produced 2-R 5-oxo 5-H 6 in the presence ofAlcohol shown in Table 1, this
-Carboxamid 7-phenyl 1,3,4-thiadiazolo-[3,2-a] reaction doesnot take a in the present of catalyst
pyrimidine(5).(Figure 2)
.To show the generality and applicability of this
procedure, we treated a wide variety of 2- R 5-oxo
In this regard synthes of 2-R 5-oxo 5-H
Table 1: Optimization of the reaction conditions
6-Carboxamid 7-phenyl -1,3,4-thiadiazolo [3,2-a]
pyrimidinedo with The aim of 2-R 5-oxo 5-H
6-ethylcarboxylate 7-phenyl 1 ,3,4-thiadiazolo
[3,2-a] pyrimidine and amin in present solvent
C2H5OH.
Entry
Solvent
Time(h)
Yielda(%)
1
2
3
4
5
H2O
8
4
4
5
6
20
85
95
60
50
CH3OH
C2H5OH
C3H7OH
C4H9OH
RESULT AND DISCUSSION
First, we tried synthesisof 2- R 5-oxo 5-H
6-Carboxamid 7-phenyl -1,3,4-thiadiazolo [3,2-a]
pyrimidinewith 2-R 5-oxo 5-H 6-ethylcarboxylate
aYields refer to isolated pure products
Table 2: Synthesisof 2- R 5-oxo 5-H 6-Carboxamid 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 amina
Entry
Thiadiazol
Amin
Product
Time(h)
Yieldb(%)
O
O
O
CONH2
1
NH3
6
82
N
N
N
N
Et
H
S
N
Ph
H
S
N
Ph
O
O
O
CONH2
Ph
2
3
4
5
NH3
NH3
NH3
NH3
8
7
6
5
85
85
90
90
N
N
N
N
Et
H3
C
S
N
H3C
S
N
O
Ph
O
O
CONH2
Ph
N
N
N
N
Et
Ph
S
N
Ph
S
N
Ph
O
N
O
O
N
CONH2
N
N
N
N
Et
Ph
S
Ph
Ph
S
Ph
O
O
O
CONH2
Ph
N
N
N
N
Et
Br
S
N
S
N
Ph
Br
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 amin
b Yields refer to isolated pure products.

MORADIVALIKBONI et al., Orient. J. Chem., Vol. 30(1), 375-378 (2014)
377
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: Synthesis of 2-R7-phenyl 6- ethylcarboxylate 5-oxo 5-H 1,3,4-thiadiazolo [3,2- a]pyrimidine
O
N
O
N
COOEt
CONH2
Ph
N
N
N
N
C2H5OH
Solvent
NH3
+
R
S
Ph
R
S
(5)
(4)
(3)
R:( H, CH3, Ph- , PhCH2-, Br)
Fig. 2: Synthesof 2- R 5-oxo 5-H 6-Carboxamid 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine
5-H 6-ethylcarboxylate 7-phenyl 1 ,3,4- thiadiazolo
[3,2-a] pyrimidine and amin in the presence of
alcohol ethanol at 78oC and obtained the desirable
products in good to excellent yields (Table 2).
CONCLUSION
In conclusion, the alcohol has been
employed as a mild, and highly efficient solvent
system for the convenient preparation of 2- R 5-oxo
5-H 6-Carboxamid 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 amin. In addition low cost,
recyclable solvent system. The advantages include
low cost, mild reaction conditions and reactions
carried out at room temperature with excellent
yields.
ExPERIMENTAL
Amixtureof2-R 5-oxo 5-H 6-ethylcarboxylate
7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine (1
mmol), amin (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.2-H 5-oxo 5-H 6-Carboxamid 7-phenyl
-1,3,4-thiadiazolo [3,2-a] pyrimidine:1H NMR (400
MHz, CDCl3, δ ppm):6 (s, 2H, NH2) ; 7.14-7.30
(5H, Ph); 7.50 (S, H).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 (C),162,1(C),
163 (C), 168
ACKNOwLEDgEMENTS
The authors are thankful to the mazandran
University Research Council for the partial support
of this research and thankful to Dr Heshmatollah
Alinezhad .
(C), 172,6.

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