A simple and efficient synthesis of novel N,N′-Bis (1H-pyrrol-1-yl)-1-[2-(2-aryl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl) ethyl]-1H-1,2,3-triazole-4,5-dicarboxamides

Article abstract of DOI:10.1002/jhet.5570440620

(Chemical Equation Presented) One-pot reaction of 3-aryl-5-methyl-1,3,4- oxadiazolin-2-ones 1a-g with ethanolamine yielded the 4-(2-hydroxyethyl)-2-aryl- 5-methyl-2,4-dihydro-3H-1,2,4-triazolin-3-ones 2a-g which were converted to the azido compounds 6a-g. These azides on 1,3-dipolar cycloaddition with DMAD afforded the dimethyl-1-[2-(2-aryl-5-methyl-3-oxo-1,2,4-triazol-4-yl)ethyl]-1H- 1,2,3-triazol-4,5-dicarboxylates 7a-g which on conversion to bishydrazides 8a-g and further cyclisation with 2,5-hexanedione afforded the title compounds 9a-g. This new short route for the so far unkown bis-(triazolinone-triazole)ethanes involves mild and convergent 1,3-dipolar cycloaddition reaction yielding overall good yields of the products.

Full text of DOI:10.1002/jhet.5570440620

Nov-Dec 2007
1363
A Simple and Efficient Synthesis of Novel N,N'-Bis (1H-pyrrol-1-
yl)-1-[2-(2-aryl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-
yl)ethyl]-1H-1,2,3-triazole-4,5-dicarboxamides
Prashant R. Latthe, Vinay A. Sunagar and Bharati V. Badami*
Post Graduate Department of Studies in Chemistry,
Karnatak University, Dharwad – 580 003, INDIA.
bbadami@rediffmail.com
Received December 29, 2006
H3C
O
N
N
C
N
N
O
O
H
H2
C
CH3
CH3
N
R
R
C
NH
N
C
O
N
H2
N
N
O
N
H3C
N
CH3
CH3
One-pot reaction of 3-aryl-5-methyl-1,3,4-oxadiazolin-2-ones 1a-g with ethanolamine yielded the 4-(2-
hydroxyethyl)-2-aryl-5-methyl-2,4-dihydro-3H-1,2,4-triazolin-3-ones 2a-g which were converted to the
azido compounds 6a-g. These azides on 1,3-dipolar cycloaddition with DMAD afforded the dimethyl-1-
[2-(2-aryl-5-methyl-3-oxo-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarboxylates 7a-g which on
conversion to bishydrazides 8a-g and further cyclisation with 2,5-hexanedione afforded the title
compounds 9a-g. This new short route for the so far unkown bis-(triazolinone-triazole)ethanes involves
mild and convergent 1,3-dipolar cycloaddition reaction yielding overall good yields of the products.
J. Heterocyclic Chem., 44, 1363 (2007).
formation of 3-arylsydnones [11a]) and hydrazine
hydrate.
INTRODUCTION
Triazoles have been of continuing interest to organic
chemists because of their use in the medicinal and
agricultural fields. 1,2,4-Triazole derivatives have been
widely used as antifungal [1], insecticidal & ascaricidal
[2], analgesic [3], vasodilatory [3], anti-inflammatory [3],
diuretic [3] and antibacterial [4] agents. The 1,2,3-triazole
moiety is a substructure of a number of biologically active
compounds [5] and a number of its derivatives have found
diverse uses in synthetic [6a], analytical [6a], medicinal
[6a] chemistry, as agrochemicals [6a], dyestuffs [6a],
fluorescent whiteners [6b] and photosensitizers [6b].
Although a significant number of triazoles are prepared
and stored, expensive starting materials or sensitive
intermediates appear to have hindered their industrial
synthesis. Most of the reported methods are multistep
procedures [2,7-9], starting from compounds that are
themselves obtained with difficulty. Though a large
number of triazoles are known there are very few
examples of the corresponding triazolinones [9a]. In view
of the importance of these triazoles we aimed to
synthesize some new heterocyclic systems containing
these isomeric triazoles through ethylene spacers and to
study their structure-activity relationship properties. Our
attempt [10] to simplify the synthesis of 1,2,4-triazolin-
ones has led to a facile and simple preparative method
starting from 3-aryl-5-methyl-[1,3,4]- oxadiazolin-2-ones
[11] (obtained in excellent yield, by one-pot ring trans-
In continuation of this work, we thought of exploring
the synthetic scope and reactivity of these oxadiazolin-
ones 1a-g towards other nitrogen nucleophiles like
phenylhydrazine and primary amines to obtain some new
substituted 1,2,4-triazolinone derivatives. However, the
oxadiazolinones were found to be unreactive towards
phenylhydrazine and aromatic amines. It appears that the
high basicity of the amines determines the ring opening of
the oxadiazolinone, because the carbonyl is not of a
lactone type but it is a lactam-lactone carbonyl which
reduces the susceptibility towards less basic aromatic
amines. Hence, we thought of using the more reactive and
basic aliphatic primary amines, amongst which we
selected the bifunctional ethanolamine for the preparation
of 4-(2-hydroxyethyl)-2-aryl-5-methyl-2,4-dihydro-3H-
1,2,4-triazolin-3- ones 2a-g.
RESULTS AND DISCUSSION
In this paper we report a simple one-pot ring conversion
of the oxadiazolinones 1a-g into the so far unknown 4-(2-
hydroxyethyl)-2-aryl-5-methyl-2,4-dihydro-3H-1,2,4-
triazolin-3-ones 2a-g by reaction with ethanolamine, in ~
80-85% yield. The mechanism of this one-pot ring
reaction may be proposed as follows (Scheme 1). The
initial step is the attack of the nucleophile on the carbonyl
carbon leading to the ring fission that subsequently
undergoes cyclization to the triazolinone ring. The

1364
P. R. Latthe, V. A. Sunagar and B. V. Badami
Vol 44
reaction progress was monitored by TLC and there was no
indication of the existence of the intermediate, suggesting
a tandem ring fission- recyclization reaction.
the corresponding chloro derivatives 3a-g were unsuc-
cessful (Scheme 2). However, these hydroxyethyl
triazolinones are of great interest as they contain a free
aliphatic -OH group, which could be utilized for a variety
of other reactions. Literature has many examples where
more potent activity has been exhibited by the acetyl
compounds, so in view of this, we converted the
hydroxyethyl compounds 2a-g to the corresponding O-
acetyl derivatives 4a-g.
Scheme 1
O
O
:
N
N
NH2 CH2 CH2 OH
+
NH CH2 CH2 OH
O
NH
N
O
CH3
CH3
In another attempt, reaction of the hydroxyethyl
compounds 2a-g with methane sulphonylchloride
afforded the mesylates 5a-g, which on further reaction
with sodium azide in DMF yielded the 2-aryl-4-(2-
azidoethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-ones
6a-g. These compounds which are the key intermediates
in the synthesis of title compounds underwent smooth 1,3-
dipolar cycloaddition with dimethyl acetylene dicarbox-
ylate (DMAD) to afford very good yield of the dimethyl-
1-[2-(2-aryl-5-methyl-3-oxo-1,2,4-triazol-4-yl)ethyl]-1H-
1,2,3-triazol-4,5-carboxylates 7a-g. Reaction of these
O
O
N
N
N
N
N
N
H
CH2 CH2 OH
OH
CH2 CH2 OH
CH3
CH3
Our purpose in preparing these hydroxyethyl deriva-
tives was to utilize them as precursors to introduce
various heterocycles through the hydroxy group. Our
attempts to convert the hydroxyethyl compounds 2a-g to
Scheme 2
O
H2
C
O
OH
C
R
N
NH2CH2CH2OH
160oC, 6 hrs
R
H2
O
N
N
N
N
CH3
CH3
2a-g
SOCl2/Pyridine
CH3SO2Cl /
Pyridine
1a-g
Stir, 15hrs
RT
Ac2O
3 hrs
O
H2
C
Cl
C
R
O
H2
C
O
S
N
H2
O
N
CH3
R
C
R
N
H2
N
O
N
CH3
O
H2
C
3a-g
N
O
CH3
O
C
N
5a-g
H2
CH3
N
NaN3/DMF
Reflux
N
CH3
4a-g
6 hrs
O
H2
C
N3
C
R
N
H2
N
N
CH3
6a-g
DMAD/Xylene
N
1200C
5 hrs
N
N
O
N
CONHNH2
H2
N
N
C
O
COOCH3
H2
C
C
R
N
N2H4.H2O
5 hrs
N
CONHNH2
H2
C
R
N
COOCH3
H2
N
N
CH3
8a-g
N
CH3
6 hrs
2,5-Hexadienone
7a-g
H3C
O
N
N
C
N
N
N
O
H2
C
H
CH3
CH3
R
C
NH
N
C
O
N
H2
N
H3C
N
CH3
9a-g
(a) R=H; (b) R=4-Br; (c) R =3-Cl; (d) R =4-Cl; (e) R =3-Me; (f) R =4-Me; (g) R =4-OMe.

Nov-Dec 2007
A Simple and Efficient Synthesis of Novel N,N'-Bis (1H-pyrrol-1-yl)-1-[2-(2-aryl-5- methyl-
3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-dicarboxamides
1365
1H-NMR (300 MHz) of these compounds showed a
singlet at ꢁ 2.36 ppm for the –CH3 protons of triazolinone
ring. A broad signal at ꢁ 2.6 ppm (1H, D2O exchanged) is
suggestive of the intermolecular hydrogen bonded –OH
group. The two distorted triplets at ꢁ3.85 and 3.95ppm
were assigned to the methylene protons –CH2a and the
deshielded –CH2b protons respectively (Figure 3) and this
pattern is in accordance with literature data [13] of similar
type of grouping. The signals at ꢁ7.37 - ꢁ7.95 were
assigned to the aromatic protons. This splitting pattern is
not clearly of the first order perhaps due to the
exchangeable proton on the oxygen, but, two clear triplets
appeared on deuteration for these AA'BB' type of protons.
The following conformation (Figure 3) was deduced from
the 1H-NOE difference spectrum of one of the compounds
2e. Enhancement in the signal of the methylene triplet at ꢁ
3.85 ppm was observed upon irradiation of the
triazolinone methyl protons at ꢁ 2.36 ppm, indicating the
close proximity of –CH2a and –CH3 in space. This
conformation with the C=O and the OH groups far apart
rules out intramolecular H-bonding while it can account
for two different intermolecular interactions as in Figures
1 and 2. We have also obtained unambiguous evidence for
this conformation by Single crystal X-ray study [14].
diesters with hydrazine hydrate gave the bis-(hydrazine-
carbonyl)compounds 8a-g which on cyclisation with 2,5-
hexanedione yielded the tetraheterocyclic N,N'-bis(1H-
pyrrol-1-yl)-1-[2-(2-aryl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-
dicarboxamides 9a-g.
CONCLUSION
Such compounds containing two isomeric triazoles -
1,2,4-triazolinone and 1,2,3-triazoles separated by an
ethylene group, were not found in the literature and
surveying the literature we find that such bistriazole
systems would be inaccessible by alternate and routine
methods. In the absence of any reported methods for such
systems we have here reasoned that they could be obtained
by a facile, convenient and an economical method from a
simple compound like sydnone (3-arylsydnones are
obtained readily from primary amines in fairly good yield
[12]). The reaction of the 3-aryl-5-methyl-[1,3,4]-oxadiazo-
lin-2-ones 1a-g with primary amines appears to be the only
efficient route for the N-substituted-1,2,4-triazolinones. The
title compounds have been prepared by constructing the
isomeric triazole rings by two cycloaddition reactions (one
with sydnone ring and another with the azide group) which
are powerful avenues for convergent synthetic routes for
heterocycles accessible with difficulty. 3-Arylsydnones -
the 1,3-dipolarophiles, on tandem reaction by reported
method [11a] yielded the oxadiazolinones 1a-g which
serve as a precursor for the 1,2,4-triazolinones, while the
azides 6a-g on 1,3-dipolar cycloaddition reaction afforded
the isomeric 1,2,3-triazole ring.
O
H2
3'
2'
6'
OH
a
3
C
4
b
C
N
1'
2
N
4'
H2
Cl
5
N
5'
1
CH3
Figure 3
The structure of these compounds was further
confirmed by its mass spectral analysis. An EIMS of a
typical compound 2d showed the molecular ion peaks at
m/z 253 and 255 (3:1, isotopic peak for chlorine), which
agrees with the molecular weight of the compound.
Spectral characterization. The IR spectra of
compounds 2a-g showed two ꢀOH bands at 3450 and 3363
cm-1 and a broad band at ~1703 cm-1for the ꢀC=O. These
absorption frequencies indicate the hydrogen bonded
interactions between the –OH and C=O groups. However,
the band for C=O group does not suggest intramolecular
hydrogen bonding. The two ꢀOH stretching bands suggest
two types of intermolecular hydrogen bondings – H-
bonding between the two hydroxy groups (Figure 1) and
the hydroxy and the carbonyl groups (Figure 2) of the two
triazolinone systems.
The acetyl derivatives 4a-g were characterized by their IR
spectra with the appearance of two ꢀC=O bands, one at ~1748
cm-1 for the O-acetyl and the other at ~1708 cm-1 for the
1
triazolinone ring. The H-NMR (300 MHz) spectra of all
these compounds showed the singlets at ꢁ 2.0 ppm and ꢁ 2.35
ppm for the –CH3 protonsof the O-acetyl and –CH3 protonsof
the triazolinone ring respectively. The two triplets at ꢁ 3.95
ppm and ꢁ 4.35 ppm corresponded to the –CH2a and the–CH2b
protons. The aromatic protons resonated at ꢁ 7.35 - 7.90ppm.
The sulfonate derivatives 5a-g were characterised by
their IR spectra, which displayed bands for the asymmetric
and symmetric ꢀS=O at 1355 cm-1 and 1170 cm-1 respectively.
The 1 H-NMR (300 MHz) spectra of all these compounds
showed the singlets at ꢁ 2.34 ppm and ꢁ 3.02 ppm for the –
CH3 protons of the triazolinone ring and the methylsufonate
respectively. The–CH2a and the–CH2b protons, now highly
deshielded due to the sulphonate group resonated
downfield as two triplets at ꢁ 4.08 ppm and ꢁ 4.45 ppm.
The IR spectra of compounds 6a-g showed a strong band at
O
N
N
O
(CH2)2
N
H
O
N
N
N
(CH2)2
O
H
CH2
CH3
O
Figure 1
N
N
N
(CH2)2
O
H
H
O
N
(CH2)2
CH3
O
CH3
N
N
Figure 2

1366
P. R. Latthe, V. A. Sunagar and B. V. Badami
Vol 44
2110 cm-1 due to ꢀN3, which confirms the formation of azido
while the antifungal activity of 2a, 2b, 2c and 2d (H, 4-
Br, 3-Cl and 4-Cl) was found to be considerably higher
than the reference drug, selectively against A. niger. The
acetylation of these compounds proved fruitful as most of
them were active against both the fungi in the order 4-Br
> 4-Cl & 4-Me > 4-H > 4-OMe. Compounds 6a-g (except
4-OCH3 which was active against M. luteus) were
moderately active against all these microbes inspite of the
presence of a potent azido group as a pharmacophore
while their cycloaddition products-the bis triazoles - 7a,
7b, 7c, 7d and 7e (H, 4-Br, 3-Cl, 4-Cl & 4-Me) were
considerably more active than the reference drugs against
M. luteus and A. niger. The bis triazolopyrroles - 9e (3-
Me) showed growth inhibition higher than the reference
drug against A. niger while 9b, 9c and 9d (4-Br, 3-Cl and
4-Cl) were active only against P. notatum. The remaining
compounds exhibited weak to moderate activity against
these microbes. The antimicrobial activities have been
compared in Table 1.
compounds. These structures were further substantiated by
1
their H-NMR (300 MHz) spectra, which showed the
absence of methylsulfonate protons at ꢁ 3.02 ppm while the
two triplets for the –CH2a and the–CH2b protons appeared
upfield at ꢁ 3.73 ppm and ꢁ 3.83 ppm respectively. An
EIMS of a typical compound 6d showed the molecular ion
peaks at m/z 188 and 190 (3:1, isotopic peak for chlorine)
which agrees with the molecular weight of the compound.
The IR spectra of dimethyl-1-[2-(2-aryl-5-methyl-3-
oxo-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarbox-
ylates 7a-g showed three ꢀC=O bands at 1740, 1720, and
1700 cm-1 due to the diester carbonyls and triazolinone
carbonyl respectively. The structures were further
1
evidenced by their H-NMR (300 MHz) spectra, which
showed two singlets at ꢁ 3.92 and ꢁ 3.99 ppm due to
diester methyl protons while the triazolinone methyl
protons and the –CH2a and the–CH2b protons appeared as a
singlet and two triplets at ꢁ 2.30, ꢁ 4.22 and ꢁ 5.00
respectively. The IR spectra of compounds 8a-g showed a
broad band in the region 3270-3391 cm-1 due to ꢀNH
vibrations of the hydrazide groups and another broad band
Table 1
Antimicrobial Activity
1
at 1667 cm-1 for the ꢀC=O vibrations. The H-NMR (300
MHz) spectra showed a singlet at ꢁ 2.46 for the
triazolinone ring methyl protons and two triplets at ꢁ 4.23
and 5.08, corresponding to –CH2a and the–CH2b protons. A
broad signal at ꢁ 12.82 was assigned to two NH protons of
the hydrazide groups, which disappeared on D2O
exchange. The IR spectra of compounds 9a-g showed a
broad band at 3213 cm-1 due to ꢀNH of amide groups and
another broad band at 1666 cm-1 corresponding to amide
Compd
Antibacterial
Zone of
Iinhibition(mm)
E.coli M.luteus
Antifungal
Zone of
inhibition(mm)
P.notatum A.niger
Norfloxacin
Griseofulvin
25
15
18
12
2a
2b
2c
2d
4a
4b
4c
4d
4e
4f
4g
5b
6g
7a
7b
7c
7d
7e
8a
8b
9b
9c
9d
9e
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
14
-
14
-
-
-
-
-
-
-
-
18
18
17
18
17
17
18
18
-
-
19
-
16
18
17
16
18
22
20
20
18
20
15
16
-
16
17
18
16
17
-
ꢀ
C=O. The triazolinone ꢀC=O appeared at 1710 cm-1. The 1H-
20
22
22
20
22
22
18
18
-
-
-
-
-
-
-
-
-
-
-
NMR (300 MHz) spectra showed two singlets in the
region ꢁ 2.08-2.18 for the four methyl protons (6H each)
on the pyrrole rings, whereas another singlet was
observed at ꢁ 2.43 for triazolinone methyl protons. The –
CH2a and the –CH2b resonated as two triplets at ꢁ 4.18 ppm
and ꢁ 5.08 ppm. The two singlets at ꢁ 5.72 and ꢁ 5.76
corresponded to pyrrole ring protons (2H each). The two
NH protons resonated as two singlets at ꢁ 11.29 and ꢁ
12.80 (different H-bonding interactions) and disappeared
on D2O exchange. The aromatic protons in all these
compounds resonated in ꢁ 7.21 – 7.90 region.
Biological evaluation. All these newly synthesized
compounds were evaluated for their antimicrobial
activities against Escherichia coli, Micrococcus luteus
bacteria and Aspergillus flavus and Penicillium notatum
fungi, with Norfloxacin and Griseofulvin as the reference
drugs respectively, at a dose of 50μgm/0.1ml in
DMF(control solvent). The halogen derivatives of all the
series of these new compounds were found to be more
active than the reference drugs and also the other
derivatives in the order 4-Br > 4-Cl > 3-Cl. The
compounds 2b and 2d (4-Br and 4-Cl) were found to
exhibit slightly enhanced activity against only M. luteus
-
19
18
18
18
-
-
-
-
EXPERIMENTAL
The IR spectra were recorded on a NICOLET-IMPACT-
410FT-IR spectrophotometer as KBr pellets. H-NMR spectra
were recorded on a Bruker AC-300 F, 300 MHz spectrometer in
CDCl3/DMSO-d6 with TMS as internal standard. The mass
1

Nov-Dec 2007
A Simple and Efficient Synthesis of Novel N,N'-Bis (1H-pyrrol-1-yl)-1-[2-(2-aryl-5- methyl-
3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-dicarboxamides
1367
spectra were recorded on MIver 14 UIC 002002 spectrometer.
Elemental analysis was obtained on Heraus C,H,N rapid
analyzer.
General Procedures. 4-(2-Hydroxyethyl)-2-aryl-5-methyl-
2,4-dihydro-3H-1,2,4 -triazol-3-ones (2a-g). 3-Aryl-5-methyl-
3H-[1,3,4]-oxadiazolin-2-ones 1a-g (0.001 mol) in excess of
ethanolamine were heated in an oil-bath at 155-160 °C for 5-6
hrs. The reaction mixture was then poured into ice cold water.
The resultant solid was collected by filtered, washed with water
and crystallised from ethanol.
4-(2-Hydroxyethyl)-5-methyl-2-phenyl-2,4-dihydro-3H-
[1,2,4]-triazolin-3-one (2a). Yield 80%; mp. 116-118°C; ir
3456-3363 (ꢀOH), 1702 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ 2.35 (s, 3H,
CH3), ꢁ2.59 (s, 1H, OH, D2O exchanged), ꢁ3.82 (t, 2H, CH2
J=5Hz), ꢁ3.92 (t, 2H, CH2, J=5Hz), ꢁ7.4-ꢁ7.9 (m, 5H, Ar-H).
Anal. Calcd. for C11H13N3O2 (219.09): C, 60.30; H, 6.02; N,
19.20 %; Found: C, 60.01; H, 5.85; N, 18.75%.
4-(2-Hydroxyethyl)-5-methyl-2-(4-bromo)phenyl-2,4-dihy-
dro-3H-1,2,4-triazol-3-one (2b). Yield 80%. mp.114-116°C; ir
3455-3363 (ꢀOH), 1702 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ 2.36 (s, 3H,
CH3) ꢁ2.55(s, 1H, OH, D2O exchanged), ꢁ3.85 (t, 2H, CH2,
J=5Hz), ꢁ3.95 (t, 2H, CH2 J=5Hz), ꢁ7.37 (d, 2H, Ar-H J=
8.2Hz). ꢁ7.95 (d, 2H, Ar-H J= 8.2Hz). Anal. Calcd. for
C11H12BrN3O2 (298.09): C, 44.36; H, 4.12; N, 14.14%; Found:
C, 44.01; H, 3.87; N, 13.75%.
8.4 Hz). Anal. Calcd. for C12H15N3O3 (249.09): C, 57.86; H,
6.10; N, 16.90%; Found: C, 57.56; H, 5.87; N, 16.46%.
4-(2-Aryl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-
yl)ethyl acetates (4a-g). The 4-(2-hydroxyethyl)-1,2,4-triazolin-
3-ones 2a-g (0.001 mol) in excess of acetic anhydride were
heated on a water- bath for 2-3 hrs. The reaction mixture was
then poured into ice-cold water. The resultant solid filtered,
washed with water and crystallised from ethanol.
4-(2-Phenyl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-
4-yl)ethyl acetate (4a). Yield 75%; mp. 90-92°C; ir 1748 (ꢀC=O
Acetyl), 1702 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ 2.08 (s, 3H, CH3 O-
Acetyl), ꢁ2 .34 (s, 1H, CH3), ꢁ3.82 (t, 2H, CH2, J=4.6Hz), ꢁ3.98
(t, 2H, CH2, J=4.6Hz), ꢁ7.36-ꢁ7.95 (m, 5H, Ar-H). Anal. Calcd.
for C13H15N3O3 (261.10): C, 59.80; H, 5.85; N, 16.15%; Found:
C, 59.46; H, 549; N, 15.80%.
4-[2-(4-Bromo)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethyl acetate (4b). Yield 85%. mp.118-
120°C; ir 1745 (ꢀC=O Acetyl), 1705 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ
2.11 (3H, s, CH3, O-Acetyl), ꢁ 2 .34 (1H, s, CH3), ꢁ 3.95 (2H, t,
CH2, J=4.6Hz), ꢁ 4.32 (2H, t, CH2, J=4.6Hz), ꢁ 7.29 (2H, d, Ar-
H J= 8.4 Hz). ꢁ 7.69 (2H, d, Ar-H J= 8.4 Hz). Anal. Calcd. for
C13H14BrN3O3 (340.10): C, 46.96; H, 4.20; N, 12.42%; Found:
C, 46.50; H, 3.85; N, 12.15%.
4-[2-(3-Chloro)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethyl acetate (4c). Yield 80% mp.102-
1
4-(2-Hydroxyethyl)-5-methyl-2-(4-chloro)phenyl-2,4-dihy-
dro-3H-1,2,4-triazol-3-one (2c). Yield 82%. mp.118-120°C; ir
104°C; ir 1748 (ꢀC=O Acetyl), 1700 (ꢀC=O);
H-NMR
(CDCl3): ꢁ 2.09 (3H, s, CH3, O-Acetyl), ꢁ 2 .29 (1H, s, CH3),
ꢁ 3.89 (2H, t, CH2, J=4.6Hz), ꢁ 4.02 (2H, t, CH2, J=4.6Hz),
ꢁ 7.43 - 7.89 (4H, m, Ar-H). Anal. Calcd. for C13H14ClN3O3
(295.55): C, 52.85; H, 4.82; N, 14.26%; Found: C, 52.55; H,
4.80; N, 13.88%.
4-[2-(4-Chloro)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethyl acetate (4d). Yield 85% mp.110-
112°C; ir 1748 (ꢀC=O Acetyl), 1708 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ
2.08 (3H, s, CH3, O-Acetyl), ꢁ 2 .34 (1H, s, CH3), ꢁ 3.95 (2H, t,
CH2, J=4.6Hz), ꢁ 4.32 (2H, t, CH2, J=4.6Hz), ꢁ 7.36 (2H, d, Ar-
H J= 8.2 Hz). ꢁ 7.89 (2H, d, Ar-H J= 8.2 Hz). Anal. Calcd. for
C13H14ClN3O3 (295.55): C, 52.85; H, 4.82; N, 14.26%; Found:
C, 52.44; H, 4.50; N, 13.75%.
1
3460-3362 (ꢀOH), 1707 (ꢀC=O); H-NMR (CDCl3):ꢁ 2.30 (s, 3H,
CH3) ꢁ2.47 (s, 1H, OH, D2O exchanged), ꢁ3.80 (t, 2H, CH2,
J=5Hz), ꢁ3.92 (t, 2H, CH2, J=5Hz), ꢁ7.35 -ꢁ 7.77 (m, 4H, Ar-H).
Anal. Calcd. for C11H12ClN3O2 (253.54): C, 52.15; H, 4.82; N,
16.92%; Found: C, 51.88, H, 4.50, N, 16.56%.
4-(2-Hydroxyethyl)-5-methyl-2-(3-chlorophenyl)-2,4-dihy-
dro-3H-1,2,4-triazol-3-one (2d). Yield 81%. mp.120-122°C; ir
1
3458-3363 (ꢀOH), 1702 (ꢀC=O); H-NMR (CDCl3):ꢁ 2.36 (s, 3H,
CH3 Triazolinone) ꢁ2.60 (s, 1H, OH, D2O exchanged), ꢁ3.85 (t,
2H, CH2, J=5Hz), ꢁ3.95 (t, 2H, CH2, J=5Hz), ꢁ7.37 (d, 2H, Ar-H
J= 8.2Hz). ꢁ7.95 (d, 2H, Ar-H J= 8.2Hz). ms: m/z 253 (M+1),
209,127. Anal. Calcd. for C11H12ClN3O2 (253.54): C, 52.15; H,
4.82; N, 16.92%; Found: C, 51.78; H, 4.47; N, 16.66%.
4-[2-(3-Methyl)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethyl acetate (4e). Yield 78%. mp.100-
102°C; ir 1744 (ꢀC=O Acetyl), 1702 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ
2.13 (3H, s, CH3, O-Acetyl), ꢁ 2 .29 (1H, s, CH3), ꢁ 3.88 (2H, t,
CH2, J=4.6Hz), ꢁ 4.01 (2H, t, CH2,, J=4.6Hz), ꢁ7.30-ꢁ7.67 (5H,
m, Ar-H). Anal. Calcd. for C14H17N3O3 (275.11): C, 61.15; H,
6.26; N, 15.26%; Found: C, 60.78; H, 5.88; N, 14.75%.
4-[2-(4-Methyl)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethyl acetate (4f). Yield 78%. mp.100-
102°C; ir 1744 (ꢀC=O Acetyl), 1702 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ
2.10 (3H, s, CH3 O-Acetyl), ꢁ 2 .35 (1H, s, CH3), ꢁ 3.92 (2H, t,
CH2, J=4.6Hz), ꢁ 4.06 (2H, t, CH2, J=4.6Hz), ꢁ 7.37 (2H, d, Ar-
H J= 8.2Hz). ꢁ 7.95 (2H, d, Ar-H J= 8.2Hz). Anal. Calcd. for
C14H17N3O3 (275.11): C, 61.15; H, 6.26; N, 15.26%; Found: C,
59.80; H, 5.80; N, 14.95%.
4-[2-(4-Methoxy)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethyl acetate ones (4g). Yield 70%. mp.88-
90°C; ir 1740 (ꢀC=O Acetyl), 1705 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ
2.15 (3H, s, CH3 O-Acetyl), ꢁ 2 .35 (1H, s, CH3), ꢁ 3 .75 (3H, s,
OCH3), ꢁ 3.83 (2H, t, CH2, J=4.6Hz), ꢁ 3.97 (2H, t, CH2,
J=4.6Hz), ꢁ 7.44 (2H, d, Ar-H J= 8.4Hz). ꢁ 7.69 (2H, d, Ar-H
J= 8.4Hz). Anal. Calcd. for C14H17N3O4 (291.10): C, 57.80; H,
5.94; N, 14.48%; Found: C, 57.42; H, 5.48; N, 14.12%.
4-(2-Hydroxyethyl)-5-methyl-2-(3-methyl)phenyl-2,4-dihy-
dro-3H-1,2,4-triazol-3-one (2e). Yield 75%. mp.106-108°C; ir
3450-3362 (ꢀOH), 1701 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ 2.27 (s, 3H,
CH3), ꢁ 2.34 (s, 3H, CH3 Triazolinone) ꢁ2.60 (s, 1H, OH, D2O
exchanged), ꢁ3.48 (t, 2H, CH2, J=5Hz), ꢁ3.90 (t, 2H, CH2,
J=5Hz), ꢁ7.28 -ꢁ 7.83 (m, 4H, Ar-H). Anal. Calcd. for
C12H15N3O2 (233.10): C, 61.85; H, 6.55; N, 18.10%; Found: C,
61.59; H, 6.18; N, 17.75%.
4-(2-Hydroxyethyl)-5-methyl-2-(4-methyl)phenyl-2,4-dihy-
dro-3H-1,2,4-triazol-3-one (2f). Yield 78%. mp. 110-112°C; ir
3450-3362 (ꢀOH), 1704 (ꢀC=O); 1 H-NMR (CDCl3): ꢁ 2.25 (s, 3H,
CH3), ꢁ 2.31 (s,3H, CH3 Triazolinone) ꢁ2.63 (s, 1H, OH, D2O
exchanged), ꢁ3.42 (t, 2H, CH2, J=5Hz), ꢁ3.82 (t, 2H, CH2,
J=5Hz), ꢁ 7.28 (d, 2H, Ar-H J= 8.2Hz), ꢁ 7.92 (d, 2H, Ar-H J=
8.2Hz). Anal. Calcd. for C12H15N3O2 (233.10): C, 61.85; H, 6.55;
N, 18.10%; Found: C, 61.46; H, 6.20; N, 17.77%.
4-(2-Hydroxyethyl)-5-methyl-2-(4-methoxy)phenyl-2,4-
dihydro-3H-1,2,4-triazol-3-one one (2g). Yield 81%. mp.118-
1
120°C; ir 3460-3362 (ꢀOH), 1707 (ꢀC=O); H-NMR (CDCl3): ꢁ
2.36 (3H, s, CH3) ꢁ2.58 (s, 1H, OH, D2O exchanged), ꢁ 3.72 (s,
3H, OCH3), ꢁ3.85 (t, 2H, CH2, J=5Hz), ꢁ3.95 (t, 2H, CH2,
J=5Hz), ꢁ7.25 (d, 2H, Ar-H J= 8.4 Hz). ꢁ 7.55 (d, 2H, Ar-H J=

1368
P. R. Latthe, V. A. Sunagar and B. V. Badami
Vol 44
2-(2-Aryl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-
2-Aryl-4-(2-azidoethyl)-5-methyl-2,4-dihydro-3H-1,2,4-
triazol-3-ones (6a-g). To the solution of compounds 4a-g
(0.005 mol) in dimethylformamide was added sodium azide
(0.33 g, 0.005 mol) in water. The mixture was refluxed for 6 hrs
and then poured into ice water. The solid separated was
collected by filtration, dried and recrystallised from ethanol.
2-Phenyl-4-(2-azidoethyl)-5-methyl-2,4-dihydro-3H-1,2,4-
triazol-3-one (6a). Yield 74%; mp. 112-114°C; ir 2115(ꢀN3)
yl)ethylmethane sulfonates (5a-g). To an ice cold solution of
methanesulphonyl chloride (0.02m) in pyridine was added 4-(2-
hydroxyethyl)-2-aryl-5-methyl-2,4-dihydro-3H-[1,2,4]-triazolin-
3-ones 2a-g (0.01 mol) in small portions. The solution was
stirred at room temperature for 15 hrs and then poured onto ice.
The separated solid was collected by filtration, washed with
water and crystallized from ethanol.
1
2-(2-Phenyl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-
4-yl)ethylmethane sulfonate (5a). Yield 72%; mp. 84-86°C; ir
1711 (ꢀC=O) 1601,; H-NMR (CDCl3): ꢁ 2.37 (s, 3H, CH3), ꢁ
3.73(t, 2H, CH2, J=4.5Hz), ꢁ 3.83 (t, 2H, CH2, J=4.5Hz), ꢁ7.21-
ꢁ7.80 (m, 5H, Ar-H). Anal. Calcd. for C11H12N6O (244.10): C,
54.09; H, 4.91; N, 34.42%; Found: C, 53.65; H, 4.45; N,
34.06%.
2-(4-Bromo)phenyl-4-(2-azidoethyl)-5-methyl-2,4-dihydro-
3H-1,2,4-triazol-3-one (6b). Yield 72%. mp. 126-128°c; ir
2107(ꢀN3) 1710 (ꢀC=O) 1600,; 1 H-NMR (CDCl3): ꢁ 2.31 (s, 3H,
CH3), ꢁ 3.78(t, 2H, CH2, J=4.5Hz), ꢁ 3.92 (t, 2H, CH2, J=4.5Hz),
ꢁ7.41 (d ,2H, Ar-H, J= 8.2 Hz). ꢁ7.73 (d, 2H, Ar-H, J= 8.2 Hz).
Anal. Calcd. for C11H11BrN6O (323.10): C, 40.99; H, 3.41; N,
26.08%; Found: C, 39.70; H, 3.16; N, 25.65%.
2-(3-Chloro)phenyl-4-(2-azidoethyl)-5-methyl-2,4-dihydro-
3H-1,2,4-triazol-3-one (6c). Yield 73%. mp. 109-111°C; ir
2110(ꢀN3) 1700 (ꢀC=O) 1604,; 1 H-NMR (CDCl3): ꢁ 2.35 (s, 3H,
CH3), ꢁ 3.70 (t, 2H, CH2, J=4.5Hz), ꢁ 3.90 (t, 2H, CH2,
J=4.5Hz), ꢁ7.24 -7.80 (d, 2H, Ar-H). Anal. Calcd. for
C11H11ClN6O (278.5): C, 47.48; H, 3.95; N, 30.21%; Found: C,
47.03; H, 3.60; N, 29.78%.
2-(4-Chloro)phenyl-4-(2-azidoethyl)-5-methyl-2,4-dihydro-
3H-1,2,4-triazol-3-one (6d). Yield 75%. mp. 115-117°C; ir
2107(ꢀN3) 1710 (ꢀC=O) 1600,; 1 H-NMR (CDCl3): ꢁ 2.31 (s,3H,
CH3), ꢁ 3.78(t,2H, CH2, J=4.5Hz), ꢁ 3.92 (t,2H, CH2, J=4.5Hz),
ꢁ7.24 (d,2H, Ar-H, J= 8.3 Hz). ꢁ 7.80 (d, 2H, Ar-H, J= 8.3 Hz).
ms: m/z 278 (M+1), 250,209, 125. Anal. Calcd. for C11H11ClN6O
(278.5): C, 47.48; H, 3.95; N, 30.21%; Found: C, 47.11; H, 3.59;
N, 29.70%.
1
1700 (ꢀC=O) 1354; H-NMR (CDCl3): ꢁ 2.34 (s, 3H, CH3,
Triazolinone), ꢁ 3.01 (s, 1H, CH3), ꢁ4.03 (t, 2H, CH2, J=4.4Hz),
ꢁ 4.51 (t, 2H, CH2, J=4.4Hz), ꢁ7.29-ꢁ7.81 (m, 5H, Ar-H). Anal.
Calcd. for C12H15N3O4S (2914): C, 54.33; H, 5.66; N, 15.84%;
Found: C, 54.03; H, 5.20; N, 15.48%.
2-[2-(4-Bromo)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethylmethane sulfonate (5b). Yield 75%. mp.
96-98°C; ir 1700 (ꢀC=O) 1354; 1 H-NMR (CDCl3): ꢁ 2.34 (s, 3H,
CH3), ꢁ3.21 (s, 1H, CH3), ꢁ 4.10 (t, 2H, CH2, J=4.4Hz), ꢁ 4.58 (t,
2H, CH2, J=4.4Hz), ꢁ7.33 (d, 2H, Ar-H J= 8.4 Hz). ꢁ7.68 (d, 2H,
Ar-H J= 8.4 Hz). Anal. Calcd. for C12H14BrN3O4S (376.14): C,
38.29; H, 3.72; N, 11.17%; Found: C, 37.85; H, 3.37; N, 10.78%.
2-[2-(3-Chloro)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-
triazol-4-yl]ethylmethane sulfonate (5c). Yield 68%. mp.101-
103°C; ir 1700 (ꢀC=O) 1354; 1 H-NMR (CDCl3): ꢁ 2.36 (s, 3H,
CH3, Triazolinone), ꢁ 3.19 (s, 1H, CH3), ꢁ 4.01 (t, 2H, CH2,
J=4.4Hz), ꢁ 4.39 (t, 2H, CH2, J=4.4Hz), ꢁ7.23 -7.81 (m, 4H, Ar-
H). Anal. Calcd. for C12H14ClN3O4S (332.59): C, 43.37; H, 4.21;
N, 12.65%; Found: C, 43.01; H, 3.80; N, 12.20%.
2-[2-(4-Chloro)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethylmethane sulfonate (5d).
Yield 68%
mp.110-112°C; ir 1708 (ꢀC=O) 1350; 1 H-NMR (CDCl3): ꢁ 2.34
(s, 3H, CH3,Triazolinone), ꢁ3.07 (s, 1H, CH3), ꢁ 4.11 (t, 2H,
CH2, J=4.4Hz), ꢁ 4.55 (t, 2H, CH2, J=4.4Hz), ꢁ7.33 (d, 2H, Ar-H
J= 8.2 Hz). ꢁ7.86 (d, 2H, Ar-H J= 8.2 Hz). Anal. Calcd. for
C12H14ClN3O4S (332.59): C, 43.37; H, 4.21; N, 12.65%; Found:
C, 43.02; H, 3.76; N, 12.26%.
2-(3-Methyl)phenyl-4-(2-azidoethyl)-5-methyl-2,4-dihydro-
3H-1,2,4-triazol-3-one (6e).
Yield 75% mp. 127-129°C; ir
1
2101(ꢀN3) 1710 (ꢀC=O) 1604,; H-NMR (CDCl3):ꢁ 2.27 (s,3H,
CH3),ꢁ 2.31 (s,3H, CH3), ꢁ 3.78 (t,2H, CH2, J=4.5Hz), ꢁ 3.97
(t,2H, CH2, J=4.5Hz), ꢁ 7.33-ꢁ7.79(m,4H, Ar-H). Anal. Calcd.
for C12H14N6O (258.11): C, 55.81; H, 5.42; N, 32.55%; Found:
C, 55.47; H, 5.17; N, 32.15%.
2-[2-(3-Methyl)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethylmethane sulfonate (5e). Yield 68%.
mp.118-120°C; ir 1700 (ꢀC=O) 1354,; 1 H-NMR (CDCl3): ꢁ 2.34
(s, 3H, CH3), ꢁ 2.36 (s, 3H, CH3,Triazolinone), ꢁ3.07 (s, 1H,
CH3), ꢁ 4.08 (t, 2H, CH2, J=4.4Hz), ꢁ 4.45 (t, 2H, CH2,
J=4.4Hz), ꢁ7.39-ꢁ7.71 (m, 4H, Ar-H). Anal. Calcd. for
C13H17N3O4S (311.15): C, 50.16; H, 5.46; N, 13.50%; Found: C,
49.82; H, 5.10; N, 13.18%.
2-[2-(4-Methyl)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethylmethane sulfonate (5f). Yield 75%.
mp.96-98°C; ir 1706 (ꢀC=O) 1359,; 1 H-NMR(CDCl3): ꢁ 2.34 (s,
3H, CH3), ꢁ 2.36 (s, 3H, CH3,Triazolinone), ꢁ3.07 (s, 1H, CH3),
ꢁ 4.08 (t, 2H, CH2, J=4.4Hz), ꢁ 4.45 (t, 2H, CH2, J=4.4Hz),
ꢁ7.23(d, 2H, Ar-H J= 8.4 Hz). ꢁ7.81 (d, 2H, Ar-H J= 8.4 Hz).
Anal. Calcd. for C13H17N3O4S (311.15): C, 50.16; H, 5.46%; N,
13.50; Found: C, 49.75; H, 5.11; N, 13.05%.
2-(4-Methyl)phenyl-4-(2-azidoethyl)-5-methyl-2,4-dihydro-
3H-1,2,4-triazol-3-one (6f). Yield 75%. mp. 127-129°C; ir
2110(ꢀN3) 1710 (ꢀC=O) 1600,; 1 H-NMR (CDCl3): ꢁ 2.37 (s,6H,
CH3), ꢁ 3.70(t,2H, CH2, J=4.5Hz), ꢁ 3.87 (t,2H, CH2, J=4.5Hz),
ꢁ7.21 (d,2H, Ar-H, J= 8.3 Hz). ꢁ7.82 (d,2H, Ar-H, J= 8.3 Hz).
Anal. Calcd. for C12H14N6O (258.11): C, 55.81; H, 5.42; N,
32.55%; Found: C, 55.36; H, 5.01; N, 32.10%.
2-(4-Methoxy)phenyl-4-(2-azidoethyl)-5-methyl-2,4-dihy-
dro-3H-1,2,4-triazol-3-one (6g). Yield 70%. mp. 131-133°C;
ir 2110(ꢀN3) 1710 (ꢀC=O) 1600,; 1 H-NMR (CDCl3): ꢁ 2.37 (s,3H,
CH3), ꢁ 3.71 (s,3H, OCH3), ꢁ 3.82(t,2H, CH2, J=4.5Hz), ꢁ 3.94
(t,2H, CH2, J=4.5Hz), ꢁ 7.37 (d,2H, Ar-H, J= 8.2 Hz). ꢁ 7.78
(d,2H, Ar-H, J= 8.2 Hz). Anal. Calcd. for C12H14N6O2 (274.10):
C, 52.55; H, 5.10; N, 30.65%; Found: C, 52.10; H, 4.75; N,
29.65%.
2-[2-(4-Methoxy)phenyl-5-methyl-3-oxo-2,4-dihydro-3H-
1,2,4-triazol-4-yl]ethylmethane sulfonate (5g). Yield 71%.
mp.112-114°C; ir 1703 (ꢀC=O) 1354; 1 H-NMR (CDCl3): ꢁ 2.29
(s, 3H, CH3), ꢁ3.07 (s, 1H, CH3,Triazolinone), ꢁ3.71 (s, 1H,
OCH3), ꢁ 3.96 (t, 2H, CH2, J=4.4Hz), ꢁ 4.32 (t, 2H, CH2,
J=4.4Hz), ꢁ7.44 (d, 2H, Ar-H J= 8.1 Hz). ꢁ7.99 (d, 2H, Ar-H J=
8.1 Hz). Anal. Calcd. for C13H17N3O5S (327.14): C, 47.70; H,
5.19; N, 12.84%; Found: C, 47.35; H, 4.81; N, 12.50%.
Dimethyl-1-[2-(2-aryl-5-methyl-3-oxo-1,2,4-triazol-4-yl)-
ethyl]-1H-1,2,3-triazol-4,5-dicarboxylates (7a-g). To the
solution of azido compounds 6a-g (0.001 mol) in dry
acetone (25 ml) was added dimethylacetylenedicarboxylate
DMAD (0.15 g, 0.001 mol) and the mixture was heated at

Nov-Dec 2007
A Simple and Efficient Synthesis of Novel N,N'-Bis (1H-pyrrol-1-yl)-1-[2-(2-aryl-5- methyl-
3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-dicarboxamides
1369
reflux for 5 hr. The solvent was removed under reduced
pressure and the residue obtained was recrystallised from
ethanol.
Ar-H, J= 8.3 Hz). Anal. Calcd. for C18H20N6O6 (416.12): C,
51.92; H, 4.80; N, 20.19%; Found: C, 51.86; H, 4.75; N,
20.13%.
Dimethyl-1-[2-(2-phenyl-5-methyl-3-oxo-1,2,4-triazol-4-yl)-
ethyl]-1H-1,2,3-triazol-4,5-dicarboxylate (7a). Yield 81%; mp.
155-157°C; ir 1738 (ꢀC=O ester), 1720 (ꢀC=O), 1701 (ꢀC=O triazole);
1 H-NMR (CDCl3): ꢁ 2.36 (s, 3H, CH3), ꢁ 3.85 (s, 3H, OCH3), ꢁ
3.97 (s, 3H, OCH3), ꢁ 4.22(t, 2H, CH2, J=4.5Hz), ꢁ 4.98 (t, 2H,
CH2, J=4.5Hz), ꢁ7.20-ꢁ7.77 (m, 5H, Ar-H). Anal. Calcd. for
C17H18N6O5 (386.12): C, 52.84; H, 4.66; N, 21.76%; Found: C,
52.48; H, 4.16; N, 21.42%.
Dimethyl-1-[2-(2-(4-bromo)phenyl-5-methyl-3-oxo-1,2,4-tria-
zol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarboxylate (7b). Yield
85%. mp. 149-151°C; ir 1744(br, ꢀC=O ester), 1700 (ꢀC=O triazole);
1 H-NMR(CDCl3): ꢁ 2.25(s, 3H, CH3), ꢁ 3.84 (s, 3H, OCH3), ꢁ
3.93(s, 3H, OCH3), ꢁ 4.20(t, 2H, CH2, J=4.5Hz), ꢁ 4.89 (t, 2H, CH2,
J=4.5Hz), ꢁ7.29 (d, 2H, Ar-H, J= 8.4 Hz). ꢁ7.82 (d, 2H, Ar-H, J=
8.4 Hz). Anal. Calcd. for C17H17BrN6O5 (465.12): C, 43.96; H,
3.66; N, 18.10%; Found: C, 43.49; H, 3.3; N, 17.77%.
Dimethyl-1-[2-(2-(3-chloro)phenyl-5-methyl-3-oxo-1,2,4-
triazol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarboxylate (7c).
Yield 73%. mp. 126-128°C; ir 1740 (br, ꢀC=O ester), 1707 (ꢀC=O
triazole); 1 H-NMR(CDCl3): ꢁ 2.31(s 3H, , CH3), ꢁ 3.88 (s, 3H,
OCH3), ꢁ 3.97(s, 3H, OCH3), ꢁ 4.22(t, 2H, CH2, J=4.5Hz), ꢁ
4.79 (t, 2H, CH2, J=4.5Hz), ꢁ7.39 - 7.76 (m, 4H, Ar-H). Anal.
Calcd. for C17H17ClN6O5 (420.57): C, 48.57; H, 4.04; N,
20.00%; Found: C, 48.22; H, 3.67; N, 19.74%.
1-[2-(2-aryl-5-methyl-3-oxo-1,2,4-triazol-4-yl)ethyl]-1H-
1,2,3-triazol-4,5-dicarbohydrazides (8a-g). To a solution of
compounds (7a-g) (0.001 mol) in 10 ml of ethanol, hydrazine
hydrate (99-100%, 0.001 mol) was added and the reaction
mixture refluxed for 5 hours. The white solid separated on
cooling was filtered, washed with water and recrystallised from
ethanol/DMF.
1-[2-(2-Phenyl-5-methyl-3-oxo-1,2,4-triazol-4-yl)ethyl]-1H-
1,2,3-triazol-4,5-dicarbohydrazide (8a). Yield 61%; mp. 167-
169°C; ir 3382, 3289(ꢀNH) 1700 (ꢀC=O triazole) 1667 (ꢀC=O); 1 H-
NMR(DMSO): ꢁ 2.28(s, 3H, CH3), ꢁ 4.18(t, 2H, CH2, J=4.5Hz),
ꢁ 5.08 (t, 2H, CH2, J=4.5Hz), ꢁ7.20-ꢁ7.66 (m, 5H, Ar-H), ꢁ
12.10(br, 2H, NH D2O exchanged). Anal. Calcd. for
C15H18N10O3 (386.12): C, 46.63; H, 4.66; N, 36.26%; Found: C,
46.27; H, 4.31; N, 35.85%.
1-[2-(2-(4-Bromo)phenyl-5-methyl-3-oxo-1,2,4-triazol-4-yl)-
ethyl]-1H-1,2,3-triazol-4,5-dicarbohydrazide (8b). Yield 65%.
mp. 184-186°C; ir 3381, 3270 (ꢀNH) 1701(ꢀC=O triazole) 1657
(ꢀC=O); 1 H-NMR (DMSO): ꢁ 2.20 (s, 3H, CH3), ꢁ 4.20 (t, 2H, CH2,
J=4.5Hz), ꢁ 5.08 (t, 2H, CH2, J=4.5Hz), ꢁ 7.12(d, 2H, Ar-H, J=
8.2 Hz), ꢁ 7.67 (d, 2H, Ar-H, J= 8.2 Hz), ꢁ 12.10 (br, 2H, NH D2O
exchanged). Anal. Calcd. for C15H17BrN10O3 (465.12): C, 38.70;
H, 3.65; N, 30.10%; Found: C, 38.33; H, 3.29; N, 29.75%.
1-[2-(2-(3-Chloro)phenyl-5-methyl-3-oxo-1,2,4-triazol-4-yl)-
ethyl]-1H-1,2,3-triazol-4,5-dicarbohydrazide (8c). Yield 60%.
mp. 144-146°C; ir 3391, 3277 (ꢀNH) 1707 (ꢀC=O triazole) 1659
Dimethyl-1-[2-(2-(4-chloro)phenyl-5-methyl-3-oxo-1,2,4-
triazol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarboxylate (7d).
Yield 80%. mp. 138-140°C; ir 1744(br, ꢀC=O ester), 1700 (ꢀC=O
triazole); 1 H-NMR (CDCl3):ꢁ 2.25(s, 3H, CH3,Triazolinone,), ꢁ
3.82 (s, 3H, OCH3), ꢁ 3.93(s, 3H, OCH3), ꢁ 4.18(t, 2H, CH2,
J=4.5Hz), ꢁ 4.89 (t, 2H, CH2, J=4.5Hz), ꢁ7.19 (d, 2H, Ar-H, J=
8.4 Hz). ꢁ7.80 (d, 2H, Ar-H, J= 8.4 Hz). Anal. Calcd. for
C17H17ClN6O5 (420.57): C, 48.57; H, 4.04; N, 20.00%; Found:
C, 48.20; H, 3.75; N, 19.74%.
1
(ꢀC=O); H-NMR (DMSO):ꢁ 2.20(s ,3H, CH3), ꢁ 4.20 (t, 2H,
CH2, J=4.5Hz), ꢁ 5.06 (t, 2H, CH2, J=4.5Hz), ꢁ 7.29 -7.67 (m,
4H, Ar-H) ꢁ 12.02 (br, 2H, NH D2O exchanged). Anal. Calcd.
for C15H17ClN10O3 (420.57): C, 42.85; H, 4.04; N, 33.33%;
Found: C, 42.49; H, 3.68; N, 32.88%.
1-[2-(2-(4-Chloro)phenyl-5-methyl-3-oxo-1,2,4-triazol-4-yl)-
ethyl]-1H-1,2,3-triazol-4,5-dicarbohydrazide (8d). Yield 67%.
mp. 157-159°C; ir 3391, 3273 (ꢀNH) 1704(ꢀC=O triazole) 1667
Dimethyl-1-[2-(2-(3-methyl)phenyl-5-methyl-3-oxo-1,2,4-
triazol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarboxylate (7e).
Yield 76% mp. 133-135°C; ir 1740 (ꢀC=O ester), 1718 (ꢀC=O),
1700 (ꢀC=O triazole); 1 H-NMR (CDCl3): ꢁ 1.91 (s, 3H, CH3), ꢁ
2.30 (s, 3H, CH3,Triazolinone,), ꢁ 3.92 (s, 3H, OCH3), ꢁ 4.03(s,
3H, OCH3), ꢁ 4.22(t, 2H, CH2, J=4.5Hz), ꢁ 5.00 (t, 2H, CH2,
J=4.5Hz), ꢁ7.31- ꢁ7.69 (m, 4H, Ar-H). Anal. Calcd. for
C18H20N6O5 (400.13): C, 54.00; H, 5.00; N, 21.00%; Found: C,
53.93; H, 4.95; N, 20.94%.
1
(ꢀC=O); H-NMR (DMSO): ꢁ 2.22(s, 3H, CH3), ꢁ 4.23 (t, 2H,
CH2, J=4.5Hz), ꢁ 5.08 (t, 2H, CH2, J=4.5Hz), ꢁ 7.29 (d, 2H, Ar-
H, J= 8.2 Hz), ꢁ 7.78 (d, 2H, Ar-H, J= 8.2 Hz), ꢁ 12.10 (br, 2H,
NH D2O exchanged). Anal. Calcd. for C15H17ClN10O3 (420.57):
C, 42.85; H, 4.04; N, 33.33%; Found: C, 42.37; H, 3.69; N,
32.80%.
1-[2-(2-(3-Methyl)phenyl-5-methyl-3-oxo-1,2,4-triazol-4-
yl)ethyl]-1H-1,2,3-triazol-4,5-dicarbohydrazide (8e). Yield
68%. mp. 173-175°C; ir 3383, 3280 (ꢀNH) 1702 (ꢀC=O triazole)
1660 (ꢀC=O); 1 H-NMR (DMSO): ꢁ 2.23(s, 3H, CH3), ꢁ 2.32(s,
3H, CH3), ꢁ 4.11(t, 2H, CH2, J=4.5Hz), ꢁ 4.98 (t, 2H, CH2,
J=4.5Hz), ꢁ 7.21 - 7.69 (m, 4H, Ar-H), ꢁ 11.98 (br, 2H, NH D2O
exchanged). Anal. Calcd. for C16H20N10O3(400.13): C, 48.00; H,
5.00; N, 35.00%; Found: C, 47.65; H, 4.75; N, 34.70%.
1-[2-(2-(4-Methyl)phenyl-5-methyl-3-oxo-1,2,4-triazol-4-yl)-
ethyl]-1H-1,2,3-triazol-4,5-dicarbohydrazide (8f). Yield 62%.
mp. 169-171°C; ir 3389, 3280 (ꢀNH) 1700 (ꢀC=O triazole) 1667
Dimethyl-1-[2-(2-(4-methyl)phenyl-5-methyl-3-oxo-1,2,4-
triazol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarboxylate (7f).
Yield 73%. mp. 141-143°C; ir 1740 (ꢀC=O ester), 1718 (ꢀC=O),
1700 (ꢀC=O triazole); 1 H-NMR (CDCl3): ꢁ 1.89 (s, 3H, CH3), ꢁ
2.36 (s, 3H, CH3,Triazolinone), ꢁ 3.88 (s, 3H, OCH3), ꢁ 3.99(s,
3H, OCH3), ꢁ 4.20(t, 2H, CH2, J=4.5Hz), ꢁ 5.02 (t, 2H, CH2,
J=4.5Hz), ꢁ7.23 (d, 2H, Ar-H, J= 8.4 Hz). ꢁ7.77 (d, 2H, Ar-H,
J= 8.4 Hz). Anal. Calcd. for C18H20N6O5 (400.13): C, 54.00; H,
5.00; N, 21.00%; Found: C, 53.93; H, 4.95; N, 20.94%.
1
(ꢀC=O); H-NMR (DMSO): ꢁ 2.18(s, 3H, CH3), ꢁ 2.28(s, 3H,
Dimethyl-1-[2-(2-(4-methoxy)phenyl-5-methyl-3-oxo-1,2,4-
triazol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarboxylate (7g).
Yield 73%. mp. 120-122°C; ir 1740 (ꢀC=O ester), 1718 (ꢀC=O),
CH3), ꢁ 4.18(t, 2H, CH2, J=4.5Hz), ꢁ 5.08 (t, 2H, CH2, J=4.5Hz),
ꢁ7.19 (d, 2H, Ar-H, J= 8.4 Hz), ꢁ7.80 (d, 2H, Ar-H, J= 8.4 Hz),
ꢁ 12.02(br, 2H, NH D2O exchanged). Anal. Calcd. for
C16H20N10O3 (400.13): C, 48.00; H, 5.00; N, 35.00%; Found: C,
47.64; H, 4.73; N, 34.75%.
1700 (ꢀC=O triazole); 1H-NMR (CDCl3):
ꢁ 2.32 (s, 3H,
CH3,Triazolinone), ꢁ 3.71(s, 3H, OCH3), ꢁ 3.88 (s, 3H, OCH3), ꢁ
3.99(s, 3H, OCH3), ꢁ 4.20(t, 2H, CH2, J=4.5Hz), ꢁ 5.02 (t, 2H,
CH2, J=4.5Hz), ꢁ7.23 (d, 2H, Ar-H, J= 8.3 Hz). ꢁ7.70 (d, 2H,
1-[2-(2-(4-Methoxy)phenyl-5-methyl-3-oxo-1,2,4-triazol-4-
yl)ethyl]-1H-1,2,3-triazol-4,5-dicarbohydrazide (8g). Yield

1370
P. R. Latthe, V. A. Sunagar and B. V. Badami
Vol 44
65%. mp. 191-193°C; ir 3389, 3280 (ꢀNH) 1700 (ꢀC=O triazole)
1667 (ꢀC=O); 1 H-NMR (DMSO): ꢁ 2.18(s, 3H, CH3), ꢁ 2.28(s,
3H, CH3), ꢁ 4.10(t, 2H, CH2, J=4.5Hz), ꢁ 4.99 (t, 2H, CH2,
J=4.5Hz), ꢁ7.31 (d, 2H, Ar-H, J= 8.4 Hz), ꢁ7.87 (d, 2H, Ar-H,
J= 8.4 Hz), ꢁ 11.96(br, 2H, NH D2O exchanged). Anal. Calcd.
for C16H20N10O4 (416.12): C, 46.15; H, 4.80; N, 33.65%; Found:
C, 45.80; H, 4.44; N, 33.29%.
N,N'-Bis(1H-pyrrol-1-yl)-1-[2-(2-aryl-5-methyl-3-oxo-2,4-
dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-
dicarboxamides (9a-g). To a suspension of compounds (8a-g)
(0.001 mol) in ethanol (15 ml) was added acetonyl acetone
(0.002 mol) and glacial acetic acid (0.5 ml) and the reaction
mixture was heated on a boiling water bath for 6 hrs. The
solution was concentrated to half of its volume and poured into
crushed ice. The separated solid was collected by filtration,
washed with water, dried and crystallized from benzene-pet
ether as white compound.
N,N'-Bis(1H-pyrrol-1-yl)-1-[2-(2-(3-methyl)phenyl-5-methyl-
3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-tria-
zole-4,5-dicarboxamides (9e). Yield 68%. mp. 223-225°C; ir
3284(ꢀNH) 1702 (ꢀC=O triazole) 1670(ꢀC=O); 1 H-NMR (DMSO):ꢁ
2.01-2.09 (s, 12H, CH3), 2.21(s, 3H, CH3), 2.37(s, 3H, CH3,
Triazolinone), ꢁ 4.11 (t, 2H, CH2, J=4.4Hz), ꢁ 5.20 (t, 2H, CH2,
J=4.4Hz), 5.71 (s, 2H, Pyrrole ring CH), 5.75 (s, 2H, Pyrrole
ring CH), ꢁ 7.28 -7.67 (m, 4H, Ar-H), ꢁ 11.35(br, 1H, NH D2O
exchanged) ꢁ 12.59(br, 1H, NH D2O exchanged). Anal. Calcd.
for C28H32N10O3 (556.25): C, 60.42; H, 5.79; N, 25.16%; Found:
C, 59.77; H, 5.43; N, 24.85%.
N,N'-Bis(1H-pyrrol-1-yl)-1-[2-(2-(4-methyl)phenyl-5-
methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-
1,2,3-triazole-4,5-dicarboxamides (9f). Yield 65%. mp. 184-
1
186°C; ir 3280 (ꢀNH) 1700 (ꢀC=O triazole) 1672 (ꢀC=O); H-NMR
(DMSO): ꢁ 2.01(s, 6H, CH3), 2.10 (s, 6H, CH3), 2.25(s, 3H,
CH3), 2.37(s, 3H, CH3, Triazolinone), ꢁ 4.21 (t, 2H, CH2,
J=4.4Hz), ꢁ 5.22 (t, 2H, CH2, J=4.4Hz), 5.70 (s, 2H, Pyrrole ring
CH), 5.75 (s, 2H, Pyrrole ring CH), ꢁ 7.11 (d, 2H, Ar-H, J= 7.8
Hz), ꢁ 7.67 (d, 2H, Ar-H, J= 7.8 Hz), ꢁ 11.26(br, 1H, NH D2O
exchanged) ꢁ 12.80(br, 1H, NH D2O exchanged). Anal. Calcd.
for C28H32N10O3 (556.25): C, 60.42; H, 5.79; N, 25.16%; Found:
C, 60.14; H, 5.44; N, 24.85%.
N,N'-Bis(1H-pyrrol-1-yl)-1-[2-(2-phenyl-5-methyl-3-oxo-2,
4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-
dicarboxamides (9a). Yield 69%; mp. 228-230°C; ir 3289 (ꢀNH
)
1705 (ꢀC=O triazole) 1672 (ꢀC=O); 1 H-NMR (DMSO): ꢁ 2.08 (s,
6H, CH3), 2.15 (s, 6H, CH3), 2.47(s, 3H, CH3, Triazolinone), ꢁ
4.18 (t, 2H, CH2, J=4.4Hz), ꢁ 5.08 (t, 2H, CH2, J=4.4Hz), 5.72
(s, 2H, Pyrrole ring CH), 5.76 (s, 2H, Pyrrole ring CH), ꢁ7.11-
ꢁ7.66 (m, 5H, Ar-H), ꢁ 11.26(br, 1H, NH D2O exchanged) ꢁ
12.80(br, 1H, NH D2O exchanged). Anal. Calcd. for
C27H30N10O3 (542.24): C, 59.77; H, 5.57; N, 25.81%; Found: C,
59.40; H, 5.21; N, 25.44%.
N,N'-Bis(1H-pyrrol-1-yl)-1-[2-(2-(4-methoxy)phenyl-5-
methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-
1,2,3-triazole-4,5-dicarboxamides (9g). Yield 70%. mp. 211-
1
213°C; ir 3277 (ꢀNH) 1705 (ꢀC=O triazole) 1668 (ꢀC=O); H-NMR
(DMSO):ꢁ 2.11(s, 6H, CH3), 2.19 (s, 6H, CH3), 2.37(s, 3H,
CH3,Triazolinone), 3.73(s, 3H, OCH3), ꢁ 4.19 (t, 2H, CH2,
J=4.4Hz), ꢁ 5.22 (t, 2H, CH2, J=4.4Hz), 5.69 (s, 2H, Pyrrole ring
CH), 5.75 (s, 2H, Pyrrole ring CH), ꢁ 7.31 (d, 2H, Ar-H, J= 8.2
Hz), ꢁ 7.86(d, 2H, Ar-H, J= 8.2 Hz), ꢁ 11.20 (br, 1H, NH D2O
exchanged) ꢁ 12.67(br, 1H, NH D2O exchanged). Anal. Calcd.
for C28H32N10O4 (572.24): C, 58.74; H, 5.62; N, 24.46%; Found:
C, 58.38; H, 5.26; N, 24.10%.
N,N'-Bis(1H-pyrrol-1-yl)-1-[2-(2-(4-bromo)phenyl-5-methyl-
3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-
4,5-dicarboxamides (9b). Yield 74%. mp. 251-253°C; ir 3270
1
(ꢀNH) 1710 (ꢀC=O triazole) 1655 (ꢀC=O); H-NMR (DMSO):ꢁ
2.13(s, 6H, CH3), 2.21 (s, 6H, CH3), 2.33(s, 3H, CH3,
Triazolinone), ꢁ 4.14 (t, 2H, CH2, J=4.4Hz), ꢁ 5.31 (t, 2H, CH2,
J=4.4Hz), 5.64 (s, 2H, Pyrrole ring CH), 5.71 (s, 2H, Pyrrole
ring CH), ꢁ 7.35 (d, 2H, Ar-H, J= 8.2 Hz), ꢁ 7.96(d, 2H, Ar-H,
J= 8.2 Hz), ꢁ 11.29 (br ,1H, NH D2O exchanged) ꢁ 12.57(br,
1H, NH D2O exchanged). Anal. Calcd. for C27H29BrN10O3
(621.24): C, 52.18; H, 4.70; N, 22.54%; Found: C, 51.75; H,
4.33; N, 22.19%.
N,N'-Bis(1H-pyrrol-1-yl)-1-[2-(2-(3-chloro)phenyl-5-methyl-
3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-tria-
zole-4,5-dicarboxamides (9c). Yield 64%. mp. 222-224°C; ir
3285(ꢀNH) 1701 (ꢀC=O triazole) 1670 (ꢀC=O); 1 H-NMR (DMSO):ꢁ
2.11 - 2.19 (s, 12H, CH3), 2.35 (s, 3H, CH3, Triazolinone), ꢁ
4.25 (t, 2H, CH2, J=4.4Hz), ꢁ 5.20 (t, 2H, CH2, J=4.4Hz), 5.72
(s, 2H, Pyrrole ring CH), 5.76 (s, 2H, Pyrrole ring CH), ꢁ 7.11 -
7.69(m, 4H, Ar-H), ꢁ 11.33 (br, 1H, NH D2O exchanged) ꢁ
12.73 (s, 1H, NH D2O exchanged). Anal. Calcd. for
C27H29ClN10O3 (576.69): C, 56.20; H, 5.04; N, 22.28%; Found:
C, 55.75; H, 4.65; N, 21.90%.
Acknowledgments. We thank Dr.G.S.Puranik, retired
Professor of Organic Chemistry and former Chairman,
Department of Chemistry, Karnatak University, Dharwad, for
encouragement and suggestions. Authors also wish to thank SIF,
Indian Institute of Science, Bangalore, Indian Institute of
Chemical Technology, Hyderabad and USIC, Karnatak
University, Dharwad, for providing spectral data.
REFERENCES
ꢀ
Author for correspondence e-mail: bbadami@rediffmail.com
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1701 (ꢀC=O triazole) 1670 (ꢀC=O); 1 H-NMR (DMSO): ꢁ 2.11(s, 6H,
CH3), 2.19 (s, 6H, CH3), 2.37(s, 3H, CH3, Triazolinone), ꢁ 4.19 (t,
2H, CH2, J=4.4Hz), ꢁ 5.22 (t, 2H, CH2, J=4.4Hz), 5.69 (s, 2H,
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C, 55.81; H, 4.66; N, 21.90%.
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Nov-Dec 2007
A Simple and Efficient Synthesis of Novel N,N'-Bis (1H-pyrrol-1-yl)-1-[2-(2-aryl-5- methyl-
3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-dicarboxamides
1371
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