New-route to synthesis and QSAR study of 1,2,4-aryl substituted triazoles

Article abstract of DOI:10.1081/SCC-200025630

Several substituted 1,2,4-triazoles have been synthesized by a new route and characterized by IR, NMR, mass spectral, and x-ray diffraction studies. The computer programme PASS for the prediction of biological activities established that these compounds a

Full text of DOI:10.1081/SCC-200025630

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New Route to Synthesis and
QSAR Study of 1,2,4‐Aryl
Substituted Triazoles
M. B. Deshmukh a , A. W. Suryawanshi a , A. R.
Mali a & S. R. Dhongade Desai a
a Department of Chemistry , Shivaji University ,
Kolhapur, 416004, India
Published online: 12 Jan 2011.
To cite this article: M. B. Deshmukh , A. W. Suryawanshi , A. R. Mali & S. R.
Dhongade Desai (2004) New Route to Synthesis and QSAR Study of 1,2,4‐Aryl
Substituted Triazoles, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 34:14, 2655-2658, DOI: 10.1081/
SCC-200025630
To link to this article: http://dx.doi.org/10.1081/SCC-200025630
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SYNTHETIC COMMUNICATIONSw
Vol. 34, No. 14, pp. 2655–2658, 2004
New Route to Synthesis and QSAR Study of
1,2,4-Aryl Substituted Triazoles
*
M. B. Deshmukh, A. W. Suryawanshi, A. R. Mali, and
S. R. Dhongade Desai
Department of Chemistry, Shivaji University, Kolhapur, India
ABSTRACT
Several substituted 1,2,4-triazoles have been synthesized by a new route
and characterized by IR, NMR, mass spectral, and x-ray diffraction
studies. The computer programme PASS for the prediction of biological
activities established that these compounds are potential candidates for
the screening.
INTRODUCTION
Triazole derivatives are known for their antibacterial, fungicidal, pesti-
cidal, hypnotic, analgesic, amoeboidic, anthelmintic, insulin promoter, acute
neurological disorder treating, nucleotide metabolism regulating, and anti-
asthmatic activities. The 1,2,4-substituted triazole derivatives are
*
Correspondence: M. B. Deshmukh, Department of Chemistry, Shivaji University,
Kolhapur 416004, India; E-mail: m_deshmukh1@rediffmail.com.
2655
DOI: 10.1080/SCC-200025630
0039-7911 (Print); 1532-2432 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

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Deshmukh et al.
anti-convulsant, hypnotic, analgesic, amoeboidic, and anthelmintic.[1–8] We
report a new route to the synthesis of 1,2,4-triaryl triazoles using accessible
starting materials.
METHODOLOGY
The basic strategy in the present investigation involved the preparation of
1,3-benzoxazine (1), followed by reaction with hydrazides. Large number of
triazole derivatives (2) were prepared and their structure was confirmed
by IR, PMR, mass spectral, x-ray, and elemental analyses. These
compounds when tested for their microbial activity showed moderate to
good activity.
EXPERIMENTAL SECTION
The melting points were determined in open capillary tubes and are
uncorrected. The purity of the compounds was checked on TLC plates coated
with silica gel-G. The IR spectra were recorded on a Beckman Acculab-10
spectrophotometer (nmax in cm21), and the 1H NMR spectra were
recorded in DMSO on a Jeol-JMS D-300 spectrometer. All the chemicals
used for the syntheses were from Merck and used without purification. The
final products were purified by column chromatography. Reactions including
hazardous medium of pyridine were carried out in well-ventilated
fume-cupboard.
Scheme 1.

Synthesis and QSAR Study of 1,2,4-Aryl Substituted Triazoles
2657
Synthesis of 2-Phenyl-benzo[d][1,3]oxazin-4-one (1)
To the solution of anthranilic acid (10 g, 0.07 mol) in pyridine, the
benzoyl chloride (20.5 g, 0.15 mol) in pyridine (25 mL) was added dropwise
at room temperature with constant stirring for 0.5 hr followed by the addition
of 5% NaHCO3 solution. The separated solid was filtered and crystallized
from ethanol to get 1. Yield 12.5 g (80%), M.P. 1208C. Anal. Found: C,
75.20; H, 4.00; N, 6.20 (C14H9NO2) required: C, 75.33; H, 4.06; N, 6.27%.
IR (KBr): nmax 1690 (C55O), 1620 cm21 (–C55N) PMR (DMSO-d6): d,
6.8–7.6 (9H, m, Ar-H) ppm.
Synthesis of 2-3-2-Chloro-phenyl-5-phenyl-(1,2,4-triazole-4-yl)-
benzoic Acid (2a)
A mixture of 1 (2.23 g, 10 mmol) and 2-chloro benzoic acid hydrazide
(1.70 g, 10 mmol) in methanol (10 mL) was refluxed in an oil bath for 1 hr
and the reaction mixture was poured into ice-cold water to form desired
crystalline solid product. Then the separated solid was filtered and recrystal-
lized from methanol and purified by column chromatography using solvent
system (acetone and ethanol) to get 2a. Yield 2.25 g, (60%). M.P. 1978C.
Anal. Found: C, 67.2; H, 3.70; N, 11.2 (C21H14ClN3O2) required: C, 67.12;
H, 3.75; N, 11.18%. IR (KBr): nmax 3520–3300 (OH), 1705 cm21 (CO).
PMR (DMSO-d6): 10.8 (–COOH), 6.2–7.2 (13H, m, Ar-H) ppm.
Synthesis of 2-3-Phenyl-5-o-tolyloxymethyl-(1,2,4-triazole-4-yl)-
benzoic Acid (2b)
A mixture of 1 (3.75 g, 10 mmol) and o-tolyloxy-acetic acid hydrazide
(1.80 g, 10 mmol) in methanol (10 mL) was refluxed in an oil bath for 1 hr
and the reaction mixture was poured into ice-cold water to get the desired
product. The separated solid was filtered and recrystallized from methanol
and purified by column chromatographic method to get 2b. Yield 2.44 g
(63.50%). M.P. 1988C. Anal. Found: C, 71.70; H, 5.00; N, 11.00
(C21H14ClN3O2) required: C, 71.68; H, 4.97; N, 10.90%. IR (KBr): nmax
3520–3330 (OH), 1705 cm21 (C55O). PMR (DMSO-d6): 2.1 (3H, s, Ar-CH3),
6.2–7.2 (13H, m, Ar-H), 10.8 (1H, s, br, D2O exchangeable, COOH) ppm.
Similarly, other derivatives were synthesized; characterized, and their
structures were confirmed on the basis of their IR, PMR, and mass spectral
and elemental analyses.

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Deshmukh et al.
The structures of the synthesized compounds were subjected to computer
programme PASS to get the predictions about the probable biological activi-
ties of the compounds. The relationship between structure and very common
activities, such as GABA-A receptor antagonist activity and lipid metabolism
regulator activity has been established.
Antimicrobial Screening
Thecompounds synthesizedwerescreenedforantimicrobial activityagainst
some Gram þve and Gram 2ve pathogenic bacterial and fungal species like
E. coli, P. valgarism B. subtilis, S. aurius, A. niger, and Phytophora species.
The screening was carried out by paper disc method, and gentamycin sulphate
and diethane M-45 were used as standards for comparison.
RESULT AND DISCUSSION
The results indicated that some compounds exhibit good antimicrobial
activity against the above mentioned bacterial and fungal species, while
some compounds have moderate antimicrobial activity against both Gram
þve and Gram 2ve bacterial and fungal species.
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Received March 3, 2004