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The Pharma Innovation Journal 2014; 3(10): 05-09
ISSN: 2277- 7695
TPI 2014; 3(10): 05-09
© 2013 TPI
www.thepharmajournal.com
Received: 27-09-2014
Accepted: 08-10-2014
Deepak Swarnkar
Department of Chemistry,
Paher University, Udaipur
( Rajasthan) 313001, India.
Rakshit A meta
Department of Chemistry, Paher
University, Udaipur ( Rajasthan)
313001, India.
Ritu Vyas
Department of Enginnering,
Paher University, Udaipur
( Rajasthan) 313001, India.
Correspondence:
Deepak Swarnkar
Department of Chemistry,
PAHER University, Udaipur
(Rajasthan) 313001, India.
Microwave assisted synthesis of some pyrazole
derivatives and their antibacterial and antifungal
activity
Deepak Swarnkar, Rakshit Ameta, Ritu Vyas
Abstract
In the present investigation, microwave assisted synthesis of 3-(4-substituted phenyl)-1-phenylprop-2-en-
1-ones (Chalcones) (1a-c) were synthesized by base catalyzed aldol condensation of p-substituted
benzaldehyde with acetophenone in the presence of piperidine.
3-(4-substituted phenyl)-1-phenylprop-2-en-1-one (Chalcones) (1a-c) was carried out with hydrazine
hydrate, phenyl hydrazine, isoniazid, nicotinic hydrazide or thiosemicarbezide in ethanol containing a
few drops of glacial acetic acid under microwave irradiation giving 3-(4-substituted phenyl)-5-phenyl-
2,3-dihydro-1H-pyrazole (2a-c), 3-(4-substituted phenyl)-2-5-diphenyl-2,3-dihydro-1H-pyrazole (3a-c),
[5-(4-substituted phenyl)-3-phenyl-2,5-dihydro-1H-pyrazole-1-yl](pyridine-4-yl)methanone (4a-c), [5-
(4-substituted phenyl)-3-phenyl-2,5-dihydro-1H-pyrazole-1-yl](pyridine-3-yl)methanone (5a-c), 5-(4-
substituted phenyl)-3-phenyl-2,5-dihydro-1H-pyrazole-1-carbothioamide (6a-c) derivatives. The
structures of the synthesized compounds were assigned on the basis of elemental analysis, IR and
1
H
NMR spectral data. The synthesized compounds have been screened for their antibacterial and antifungal
activities.
Keywords: 3-(4-Substituted phenyl)-1-phenylprop-2-en-1-one, Antibacterial, Antifungal activities,
Microwave irradiation.
1. Introduction
Microwave assisted organic synthesis has opened up some new opportunities. Microwave
assisted synthesis is an eco-friendly method, where reactions occurs more rapidly, safely with
higher chemical yields compared to the conventional methods of synthesis.
The pyrazole unit is one of the core structures in a number of drugs. More recently extensive
studies have been focused on pyrazole derivatives exhibiting anti-inflammatory
1
, anti-cancer
2
,
anti-malarial
[3]
, antihyperglycemic
[4]
, analgesic
[5]
, anticonvulsant
[6]
, antidepressant
7
,
antiulcer
[8]
, antidiabetic
[9]
, cytotoxic
[10]
, antitubercular
[11]
, antibacterial
[12]
, antifungal
[13]
,
herbicidal and insecticidal
[14-16]
.
A synthesis of α,β-unsaturated ketones were achieved by microwave- assisted base catalysed
aldol condensation of acetophenone with p-substituted benzaldehyde. Chalcones undergo a
cyclization reaction with corresponding hydrazines giving pyrazole derivatives.
2. Materials and Methods
The melting points were determined in open capillary tube and are uncorrected. The IR spectra
were recorded on Perkin-Elmer 157 spectrometer using KBr pellets. The
1
H NMR spectra
were scanned on a DRX-300 MHz spectrometer (300 MHz) in CDCl3/DMSO-d6 using TMS
as internal standard and chemical shifts are expressed in δ ppm. Purity of synthesized
compounds was checked by TLC using silica gel-G. Spots were exposed in an iodine chamber.
General procedure for preparation of chalcone (1a-c)
A convenient route for the synthesis of α,β-unsaturated ketones (Chalcone) was achieved by
the reaction of p-substituted benzaldehyde (0.005 mol) with acetophenone (0.005 mol) in the
presence of piperidine, under microwave irradiation at 5 sec intervals. The specific reaction
time was kept 2 min and then the reaction mixture was cooled in crushed ice. Progress of the
reaction was monitored by TLC method. The solid thus obtained was filtered, washed with
water, dried and purified by recrystallization from ethanol.