EuropeanJournalofChemistry1(1)(2010)3336

EuropeanJournalofChemistry
Journalhomepage:www.eurjchem.com

SynthesisofsomenovelSchiffbasescontaining1,2,4triazolering

AkbarMobinikhaledia,*,NaserForoughifara,b,MansoorehKhanpoura andSattarEbrahimic
aDepartmentofChemistry,FacultyofSciences,ArakUniversity,Arak,IR38156,Iran

bFacultyofChemistry,IslamicAzadUniversity,NorthTehranBranch,IR19395,Iran

cDepartmentofChemistry,FacultyofSciences,IslamicAzadUniversityMalayer,Malayer,IR65718117,Iran

*Correspondingauthorat:DepartmentofChemistry,FacultyofSciences,ArakUniversity,Arak,IR38156,Iran.Tel.:+98.861.2777225;fax:+98.861.2774031.Email
address:akbar_mobini@yahoo.com(A.Mobinikhaledi).

ARTICLEINFORMATION
Received:7February2010
Receivedinrevisedform:26February2010
Accepted:8March2010
Online:31March2010

KEYWORDS
1,2,4triazole
Schiffbases
Acetohydrazide
Synthesis
Heterocycliccompounds

ABSTRACT
was prepared under facile condition via the
4Allyl5piridine4yl4H1,2,4triazole3thiol
formation of 2isonicotinoylNallylhydrazinecarbothioamide. In addition, ethyl[(4allyl5
pyridine4yl4H124triazole3yl)thio]acetatewassynthesized viathereactionof4allyl
5piridine4yl4H1,2,4triazole3thiolwithethylchloroacetate.2[(4Allyl5pyridine4yl
4H1,2,4triazole3yl)thio]acetohydrazide obtained by using ethyl[(4allyl5pyridine4yl
4H124triazole3yl)thio]acetateasaprecursorbytwosteps,wasconvertedtoSchiffbase
derivatives, 6aj. All synthesized compounds were characterized by elemental analyses, IR
spectroscopy,1HNMRand13CNMRspectroscopy. Thecis/transconformersofEisomerwere
presentinDMSOsolutionofcompounds6aj.

1.Introduction

The chemistry of 1,2,4triazoles and their fused

heterocyclic derivatives have received considerable attention
owing to their synthetic and effective biological importance.
For example, a large number of 1,2,4triazoles have been
incorporated into a wide variety of therapeutically interesting
drugcandidatesincludingantiinflammatory[1,2],antiviral[3],
analgesic [4], antimicrobial [57], anticonvulsant [8] and
antidepressant activities [9]. The hybrid molecules composed
ofthecombinationofaheterocyclicringandaSchiffbasemay
exertpotentiallybiologicalactivities.SomeSchiffbasesbearing
triazoles have been reported to be used as drugs with
considerablebiologicalactivities[1016].
Inviewofthisreportandalsoduetotheconnectionsofour
studies on the synthesis of substituted triazoles [17,18], we
turned our attention to synthesis of some new 1,2,4triazole
derivatives and their related Schiff bases obtained from the
reaction of 2(4allyl5(pyridine4yl)4H1,2,4triazol3
ylthio)acetohydrazide,5,withvariousaldehydes(Scheme1).

2.Experimental

2.1.Instrumentation

Purity of the compounds were checked by thin layer

chromatography (TLC) using C2H5OH:nhexane (1:1) as an
eluent.IRspectrawerepreparedontheMattsonGalaxyseries
FTIR 5000 spectrophotometer using KBr discs. NMR spectra
were recorded on Bruker spectrophotometer (300 MHz) in
DMSOd6 or CDCl3 using TMS as an internal standard.
Microanalyses were performed by the Elemental Analyzer
(VarioELIII)attheArakUniversity.

2.2. Synthesis of 2isonicotinoylNallylhydrazinecarbothio

amide,2
A mixture of isonicotinic acid hydrazide, 1, (0.01 mol,
1.3700 g) and allyl isothiocyanate (0.01 mol, 0.9900 g) was
refluxed in ethanol (30 mL) for 2 h. After cooling, the formed
product was collected by filtration and recrystallized from
ethanol to give thiosemicarbazide, 2. Yield: 95% (2.2420 g),
M.p.:227230oC.IR(KBr,,cm1):3070(aromaticCHstretch.),
3200, 3259 (NH), 2928 (CH), 1678 (C=O), 1554, 1440 (C=C
ringstretch.),1352(C=S).1HNMR(DMSOd6,,ppm):10.68(s,
1H,NH),9.49(s,1H,NH),8.758.77(d,2H,J=4.6Hz,ArH),8.39
(s,1H,NH),7.817.89(d,2H,J=4.7Hz,ArH),5.765.88(m,1H,
C=CHC),5.035.16(m,2H,CH2=CC),4.11(s,2H,CH2).13CNMR
(DMSOd6, , ppm): 46.4, 115.7, 122.1, 135.4, 140.0, 150.6,
164.9,182.2.
2.3. Synthesis of 4allyl5pyridine4yl4H1,2,4triazole3
thiol,3
Asolutionofthiosemicarbazide,2,(0.005mol,1.1800g)in
2NNaOH(10mL)wasrefluxedfor3h.Theresultingsolution
wascooledtoroomtemperatureandacidified(pH=3)with2N
HCl. The precipitate was filtered and washed with water. The
compound obtained was dried and crystallized from
DMF:C2H5OH(1:2)togivecompound3.Yield(0.9920g)91%.
M.p.:219221oC.IR(KBr,,cm1):3070(aromaticCHstretch.),
2733(SH),1568,1438(C=Cringstretch).1HNMR(DMSOd6,,
ppm):14.27(s,1H,SH),8.76(d,2H,J=4.8Hz,ArH),7.71(d,2H,
J= 4.8 Hz, ArH), 5.805.92 (m, 1H, C=CHC), 5.125.16 (m, 1H,
CH2=CC),4.814.89(m,1H,CH2=CC),4.79(br,2H,CH2).Anal.
Calcd.forC10H10N4S:C,55.02;H,4.69;N,25.67;S,14.69.Found:
C,54.82;H,4.51;N,25.44;S,14.44%.

EuropeanJournalofChemistry
ISSN21532249(Print)/ISSN21532257(Online)2010EURJCHEM
DOI:10.5155/eurjchem.1.1.3336.5

34

Mobinikhaledietal./EuropeanJournalofChemistry1(1)(2010)3336
S
O

NHNH2

NHNHC

NH
NCS

NaOH (2N)

SH

N
N

3
ClCH2CO2Et

N
N

KOH
N

O
S

NH2NH2

NHNH2

ArCHO

N
N

COEt

O
S

NHN

N
6a-j

CHAr

Ar
6a: C6H5
6b: 4-(NO2)-C6H4
6c: 3-(NO2)-C6H4
6d: 2-(OH)-C6H4
6e: 5-(Br)-2-(OH)-C6H3
6f : 3,4-(OH)2-C6H3
6g: 4-(CH3)-C6H4
6h: 3,4-(OCH3)2-C6H3
6i : 4-Cl-C6H4
6j : 4-Br-C6H4

Scheme1.SyntheticpathwayforpreparationofSchiffbases6aj.

2.4. Synthesis ethyl[(4allyl5pyridine4yl4H1,2,4triazo

le3yl)thio]acetate,4
To a solution of compound 3 (0.003 mol, 0.6500 g) in
absolute ethanol (20 mL), ethyl chloroacetate (0.006 mol,
0.7320g)wasadded.Themixturewasrefluxedunderstirring
for30mininthepresenceofKOH(0.003mol,0.1680g).Then,
the solvent was removed under reduced pressure to give the
solid product. The crude product was recrystallized from
H2O:C2H5OH (1:1) to give compound 4. Yield (0.6617 g) 73%.
M.p.:143145oC.IR(KBr,,cm1):3069(aromaticCHstretch.),
2968 (CH), 1732 (C=O), 1602 (C=N), 1199 (CO). 1H NMR
(CDCl3, , ppm): 8.78 (d, 2H, J=4.8 Hz, ArH), 7.68 (d, 2H, J=4.8
Hz,ArH),5.886.12(m,1H,C=CHC),(m,1H,CH2),5.395.43(m,
1H, CH2=CC), 5.015.07 (m, 1H, CH2=CC), 4.72 (br, 2H, C=C
CH2),4.22(q,2H,J=7.1Hz,CH2),4.14(s,2H,SCH2),1.30(t,3H,
J=7.0Hz,CH3). 13CNMR(CDCl3,,ppm):14.0,35.2,47.0,62.0,
18.4,122.0,131.0,134.4,150.3,152.0,153.5,168.0.Anal.Calcd.
forC14H16N4O2S:C,55.25;H,5.30;N,18.41;S,10.53.Found:C,
55.02;H,5.22;N,18.20;S,10.34%.
2.5. Synthesis of 2[(4allyl5pyridine4yl4H1,2,4triazo
le3yl)thio]acetohydrazide,5
80%hydrazinehydrate(0.003mol,0.15g)wasaddedto4
(0.002mol,0.6080g)inethanol(10mL)indropsandrefluxed
for2h.Thesolventwasthenremovedunderreducedpressure
andasolidwasobtained.Next,theprecipitatewasfilteredand
recrystallized from CCl4 to give the pure acetohydrazide 5.
Yield(0.4930g)85%.M.p.:143145 oC.IR(KBr,,cm1):3286
3196 (NH2), 3234, (NH), 3024 (aromatic CH stretch.), 1672
(C=O), 1604 (C=N), 1547, 1456 (C=C ring stretch.). 1H NMR
(CDCl3, , ppm): 8.788.80 (d, d, 2H, J=4.5 Hz, 1.4 Hz, ArH),
7.587.60 (d, d, 2H, J=4.5 Hz, 1.5 Hz, ArH), 5.926.01 (m, 1H,
C=CHC),5.405.44(m,1H,CH2=CC),5.045.10(m,1H,CH2=C
C), 4.62 (br, 2H, CH2), 3.96 (s, 2H, SCH2). Anal. Calcd. for
C12H14N6O2S: C, 49.64; H, 4.86; N, 28.95; S, 11.04. Found: C,
49.49;H,4.75;N,28.74;S,10.81%.
2.6.Generalprocedureforthesynthesisofcompounds6aj
A solution of acetohydrazide, 5, (0.0006 mol, 0.1740 g) in
ethanol(7mL),theappropriatealdehyde(0.0006mol)and45

drops of glacial acetic acid (as a catalyst) was refluxed for a

predeterminedtimeframe(Table1).Theresultantwasallowed
to cool andpoured into cold water (1520 mL).The solid was
collected by filtration and recrystallized from ethanol to give
thepureacetohydrazide6aj.

N'benzylidene2[(4allyl5pyridine4yl4H1,2,4triaz
ole3yl)thio]acetohydrazide, 6a: IR (KBr, , cm1): 3203
(NH), 3051 (aromatic CH stretch.), 1689 (C=O), 1608 (C=N),
1577,1456(C=Cringstretch.),761(CSC). 1HNMR(DMSOd6,
, ppm): 11.82 and 11.71 (s, 1H, NH, trans/cis conformers),
8.728.76 (m, 2H, ArH), 8.19 and 8.02 (s, 1H, N=CH, trans/cis
conformers), 7.617.70 (m, 4H, ArH), 7.407.42 (m, 3H, ArH),
5.976.03 (m, 1H, C=CHC), 5.235.27 (m, 1H, CH2=CC), 4.83
4.89(m,1H,CH2=CC),4.77(d,2H,J=1.8Hz,CH2),4.53and4.15
(s,2H,SCH2,trans/cisconformers).Anal.Calcd.forC19H18N6OS:
C,60.30;H,4.79;N,22.21;S,8.47.Found:C,60.11;H,4.71;N,
22.09;S,8.38%.
N'4Nitrobenzylidene2[(4allyl5pyridine4yl4H1,2,
4triazole3yl)thio]acetohydrazide, 6b: IR (KBr, , cm1):
3080 (aromatic CH stretch.), 1679 (C=O), 1601 (C=N), 1450,
1516(C=Cringstretch.),1342,1500(NO2).1HNMR(DMSOd6,
, ppm): 12.01 (br,1H, NH), 8.718.76 (m, 2H, ArH), 8.258.31
(m,2H,ArH),8.10(s,1H,N=CH),7.927.99(m,2H,ArH),7.60
7.67(m,2H,ArH),5.966.08(m,1H,C=CHC),5.245.28(m,1H,
CH2=CC), 4.794.80 (m, 1H, CH2=CC), 4.79 (br, 2H, CH2), 4.55
and 4.17 (s, 2H, SCH2, trans/cis conformers). Anal. Calcd. for
C19H17N7O3S: C, 53.89; H, 4.05; N, 23.15; S, 7.57. Found: C,
53.61;H,3.97;N,22.97;S,7.41%.

N'3Nitrobenzylidene2[(4allyl5pyridine4yl4H1,2,
4triazole3yl)thio]acetohydrazide, 6c: IR (KBr, , cm1):
3212 (NH), 3074 (aromatic CH stretch.), 1689 (C=O), 1608
(C=N), 13521529 (N=O). 1H NMR (DMSOd6, , ppm): 12.06
and 11.93 (s, 1H, NH, trans/cis conformers), 8.728.76 (m, 2H,
ArH),8.53and8.47(s,1H,N=CH,trans/cisconformers),8.12
8.33(m,3H,ArH),7.607.75(m,3H,ArH),6.00(br,1H,C=CHC),
5.255.28 (m, 1H, CH2=CC), 4.834.89 (m, 1H, CH2=CC), 4.79
(br,2H,CH2),4.55and4.17(s,2H,SCH2,trans/cisconformers).
Anal.Calcd.forC19H17N7O3S:C,53.89;H,4.05;N,23.15;S,7.57.
Found:C,53.57;H,3.93;N,23.01;S,7.38%.

Mobinikhaledietal./EuropeanJournalofChemistry1(1)(2010)3336

N'2Hydroxybenzylidene2[(4allyl5pyridine4yl4H
1,2,4triazole3yl)thio]acetohydrazide,6d:IR(KBr,,cm
1): 3435 (OH), 3213 (NH), 3047 (aromatic CH stretch.), 2982
(CH), 1685 (C=O), 1608 (C=N); 1H NMR (DMSOd6, , ppm):
12.98 and 11.62 (s, 1H, NH, trans/cis conformers), 10.95 and
10.06 (s, 1H, OH, trans/cis conformers), 8.738.76 (d, d, 2H,
J=4.3 Hz, 1.5 Hz, ArH), 8.32 and 8.42 (s, 1H, N=CH, trans/cis
conformers), 7.217.32 (m, 1H, ArH), 7.547.67 (m, 3H, ArH),
6.856.92 (m, 2H, ArH), 5.986.09 (m, 1H, C=CHC), 5.245.30
(m,1H,CH2=CC),4.844.90(d,d,1H,J=17.3Hz,3.4Hz,CH2=C
C), 4.77 (br, 2H, CH2), 4.51 and 4.14 (s, 2H, SCH2, trans/cis
conformers).Anal.Calcd.forC19H18N6O2S:C,57.85;H,4.60;N,
21.31;S,8.13.Found:C,57.54;H,4.51;N,21.10;S,7.95%.
N'5Bromo2hydroxybenzylidene2[(4allyl5pyridine
4yl4H1,2,4triazole3yl)thio]acetohydrazide, 6e: IR
(KBr,,cm1):3431(OH),3175(NH),2978(CH),1674(C=O),
1606(C=N).1HNMR(DMSOd6,,ppm):11.54and11.47(s,1H,
NH, trans/cis conformers), 9.29 (s, 1H, OH), 9.43 (s, 1H, OH),
8.74 (br, 2H, ArH), 7.88 and 7.83 (s, 1H, N=CH, trans/cis
conformers), 7.627.67 (m, 2H, ArH), 7.15 (br, 1H, ArH), 6.87
6.92(m,1H,ArH),6.76(br,1H,ArH),5.966.06(m,1H,C=CH
C), 5.235.27 (m, 1H, CH2=CC), 4.834.89 (m, 1H, CH2=CC),
4.77 (br, 2H, CH2), 4.50 and 4.09 (s, 2H, SCH2, trans/cis
conformers). Anal. Calcd. for C19H18N6BrO2S: C, 48.21; H, 3.62;
N,17.75;S,6.77.Found:C,47.96;H,3.55;N,17.41;S,6.59%.
N'3,4Dihydroxybenzylidene2[(4allyl5pyridine4yl
4H1,2,4triazole3yl)thio]acetohydrazide, 6f: IR (KBr, ,
cm1): 3429 (OH), 3178 (NH), 3033 (aromatic CH stretch.),
1674 (C=O), 1605 (C=N). 729 (CSC), 1H NMR (DMSOd6, ,
ppm):12.06and11.68(s,1H,NH,trans/cisconformers),8.73
8.76 (m, 2H, ArH), 11.03 and 10.40 (s, 1H, OH, trans/cis
conformers),8.38and8.24(s,1H,N=CH,trans/cisconformers),
7.77 (br, 1H, ArH), 7.607.66 (m, 2H, ArH), 7.377.43 (m, 1H,
ArH),6.846.90(m,1H,ArH),5.986.05(m,1H,C=CHC),5.24
5.28(m,1H,CH2=CC),4.854.90(m,1H,CH2=CC),4.78(br,2H,
CH2), 4.50 and 4.13 (s, 2H, SCH2, trans/cis conformers). Anal.
Calcd. for C19H18N6O3S: C, 55.60; H, 4.42; N, 20.48; S, 7.81.
Found:C,55.31;H,4.34;N,20.32;S,7.56%.
N'4Methylbenzylidene2[(4allyl5pyridine4yl4H1,
2,4triazole3yl)thio]acetohydrazide, 6g: IR (KBr, , cm1):
3205 (NH), 3047 (aromatic CH stretch.), 2931 (CH), 1697
(C=O), 1606 (C=N), 1375, 1450 (CH3). 1H NMR (DMSOd6, ,
ppm):11.73and11.63(s,1H,NH,trans/cis,conformers),8.75
(d, 2H, J=4.8 Hz, ArH), 7.97 and 8.15 (s, 1H, N=CH, trans/cis
conformers), 7.547.67 (m, 4H, ArH), 7.227.27 (m, 2H, ArH),
5.976.07 (m, 1H, C=CHC), 5.235.27 (m, 1H, CH2=CC), 4.77
4.88(m,1H,CH2=CC),4.55(br,2H,CH2),4.12and4.50(s,2H,
SCH2, trans/cis conformers), 2.32 (s, 3H, CH3). Anal. Calcd. for
C20H20N6OS:C,61.20;H,5.14;N,21.41;S,8.17.Found:C,61.00;
H,5.30;N,21.11;S,8.32%.
N'3,4Dimethoxylbenzylidene2[(4allyl5pyridine4yl
4H1,2,4triazole3yl)thio]acetohydrazide,6h
IR(KBr,,cm1):3205(NH),3050(aromaticCHstretch.),2962
(CH),1680(C=O),1602(C=N),1512,1438(C=Cringstretch.).
1H NMR (DMSOd6, , ppm): 11.95 and 11.59 (s, 1H, NH,
trans/cisconformers),8.728.76(br,2H,ArH),8.11and7.93(s,
1H,N=CH,trans/cisconformers),7.59(s,1H,ArH),7.19(t,1H,
J=8.5 Hz, ArH), 6.99 (t, 1H, J=8.5 Hz, ArH), 5.976.06 (m, 1H,
C=CHC), 5.24 (d, 1H, J=10.5 Hz, CH2=CC), 4.824.90 (m, 1H,
CH2=CC), 4.77 (br, 2H, CH2), 4.48 and 4.11 (s, 2H, SCH2,
trans/cis conformers), 3.79 (s, 6H, 2OCH3). Anal. Calcd. for
C21H22N6O3S: C, 57.52; H, 5.06; N, 19.17; S, 7.31. Found: C,
57.82;H,5.03;N,19.00;S,7.61%.

35

N'4Chlorobenzylidene2[(4allyl5pyridine4yl4H1,
2,4triazole3yl)thio]acetohydrazide, 6i: IR (KBr, , cm1):
3205 (NH), 3040 (aromatic CH stretch.), 1697 (C=O), 1606
(C=N), 1547, 1440 (C=C ring stretch.), 827 (CCl). 1H NMR
(DMSOd6, , ppm): 11.86 and 11.75 (s, 1H, NH, trans/cis
conformers), 8.738.76 (br, 2H, ArH), 8.19 and 8.00 (s, 1H,
N=CH,trans/cisconformers),7.607.74(m,4H,ArH),7.477.52
(m, 2H, ArH), 5.986.07 (m, 1H, C=CHC), 5.245.27 (m, 1H,
CH2=CC), 4.834.88 (m, 1H, CH2=CC), 4.77 (br, 2H, CH2), 4.53
and 4.13 (s, 2H, SCH2, trans/cis conformers). Anal. Calcd. for
C19H17ClN6OS: C, 55.27; H, 4.15; N, 20.35; S, 7.77. Found: C,
54.95;H,4.31;N,20.00;S,7.40%.
N'4Bromobenzylidene2[(4allyl5pyridine4yl4H1,
2,4triazole3yl)thio]acetohydrazide, 6j: IR (KBr, , cm1):
3207 (NH), 3033 (aromatic CH stretch.), 1686 (C=O), 1606
(C=N).1HNMR(DMSOd6,,ppm):11.85and11.74(s,1H,NH,
trans/cisconformers),8.75(d,2H,J=5.2Hz,ArH),8.17and7.98
(s, 1H, N=CH, trans/cis conformers), 7.607.67 (m, 6H, ArH),
6.016.07 (m, 1H, C=CHC), 5.245.27 (m, 1H, CH2=CC), 4.77
4.89(m,1H,CH2=CC),4.77(br,2H,CH2),4.51and4.13(s,2H,
SCH2, trans/cis conformers). Anal. Calcd. for C19H17BrN6OS: C,
49.90; H, 3.75; N, 17.47; S, 7.01. Found: C, 49.70; H, 3.66; N,
17.31;S,6.82%.
3.ResultsandDiscussion
In continuation of our efforts to develop the synthesis of
thenewfusedheterocyclicandSchiffbases[1921]wereport
herein,asimpleandefficientmethodforthesynthesisofsome
novel Schiff bases containing 1,2,4triazole ring. Our synthetic
approaches are depicted in Scheme 1. Initial compound was
prepared from available isonicotinic acid hydrazide, 1. 2
IsonicotinoylNallylhydrazinecarbothioamide,2,wasprepared
byreactionofcompound1withallylisothiocyanateinethanol.
The cyclization of compound 2 in the presence of sodium
hydroxide resulted in the formation of 4allyl5pyridine4yl
4H1,2,4triazole3thiol,3.Thereactionoftriazole3withethyl
chloroacetateinthepresenceofpotassiumhydroxideproduced
ethyl[(4allyl5pyridine4yl4H1,2,4triazole3yl)thio]aceta
te 4, which then converted to 2[(4allyl5pyridine4yl4H
1,2,4triazole3yl)thio]acetohydrazide,5,viathereactionwith
hydrazine hydrate. The treatment of acetohydrazide 5 with
several aldehydes gave N'substituebenzylidene2[(4allyl5
pyridine4yl4H1,2,4triazole3yl)thio]acetohydrazide, 6aj,
(Scheme1).TheresultsareshowninTable1.Thecompounds
having arylidenhydrazid structure may exist as E/Z
geometrical isomers about CH=N double bond and cis/trans
amide conformers (Scheme 2) [2224]. According to the
literature [23,24], compounds containing imine bonds are
present in higher percentage in dimethyld6 sulfoxide solution
in the form of geometrical E isomer about C=N double bond.
The Z isomer can be stabilized in less polar solvent by an
intramolecular hydrogen bond. In the present study, the
spectral data were obtained in DMSOd6 and no signal
belongingtotheZisomerwasobserved.Ontheotherhand,the
cis/trans conformers of the E isomer were present in DMSO
solutionofcompounds6aj.

Table1.SynthesizedSchiffbases6aj.
Compound
Ar*
Time(h)
6a
C6H5
6
6b
4(NO2)C6H4
8
6c
3(NO2)C6H4
7
6d
2(OH)C6H4
1
6e
5(Br),2(OH)C6H3
0.5
6f
3,4(OH)2C6H3
0.5
6g
4(CH3)C6H4
4
6h
3,4(OCH3)2C6H3
3
6i
4(Cl)C6H4
3
6j
4(Br)C6H4
2
*Scheme1.

M.p.(oC)
102104
201203
164165
160161
213215
234236
119122
248251
128130
183185

Yield(%)
62
55
54
83
75
73
81
74
77
68

36

Mobinikhaledietal./EuropeanJournalofChemistry1(1)(2010)3336

O
trans, Z

trans, E

C
N

Z=

Z
Ar

Ar

N
N

SCH2

H
H

O
O
C

Ar

N
C

C
N

Ar
Z

Z
cis, Z

cis, E

Scheme2.E/ZGeometricalisomersandcis/trans conformersof6aj.

The structures of the synthesized compounds were

determinedonthebasisofspectraldataanalysisincludingIR,
1H NMR and 13C NMR. The 1H NMR spectrum of compound 2
showed two characteristic absorptions (singlet at =9.49 ppm
and =10.68 ppm) attributed to the NH groups, which were
disappearedbytheformationofthetriazole3.Inthe 1HNMR
spectrum of compound 4, additional signals derived from the
estergroupwereobservedat1.30(OCH2CH3),4.14(SCH2) and
4.22 OCH2CH3) ppm. The 1H NMR spectra of 6aj displayed
additional signals due to the aromatic ring derived from
aldehyde moiety at the aromatic region, while the signal
belonging to the NH2 group of hydrazide structure was not
appeared. In the 1H NMR spectra of compounds 6aj two
signalseachbelongingtotheSCH2,N=CHandNHgroupsofcis
andtransconformerswereobservedbetween3.984.55,7.97
9.85and11.4712.00ppm,respectively.
Acknowledgement

The authors gratefully acknowledge the financial support

fromtheResearchCouncilofArakUniversity.

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