Synthesis and characterization of 3-(1-hydroxy naphthalene-2-yl)-5-(furan- 2-yl)-1-substituted pyrazolines

Article abstract of DOI:10.13005/ojc/300150

2-acetyl-1-naphthol 2 is prepared by Modified Nenchi's method which on treatment with furfuraldehyde and KOH gives 1-(1-hydroxy naphthalen-2-yl)-3- (furan-2-yl) prop-2-ene-1-ones 3 in excellent yield. The chalcone 3 when subjected to hydrazine/phenyl hydrazine/semicarbazide/2,4 dinitro phenyl hydrazine/isonicotinic acid hydrazide in DMF solvent gives 3-(1-hydroxy naphthalene-2-yl)-5-(furan-2-yl)-1-substituted pyrazolines 4, 5, 6, 7 and 8 in 35-45% yield. The structural assignments to the compounds 4, 5, 6, 7 and 8 are based on their elemental analysis and spectral data.

Full text of DOI:10.13005/ojc/300150

ISSN: 0970-020 X
CODEN: OJCHEG
2014, Vol. 30, No. (1):
Pg. 361-363
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Synthesis and Characterization of 3-(1-hydroxy naphthalene-
2-yl)-5-(furan-2-yl)-1-substituted pyrazolines
S.E. BHANDARkAR
Department of Chemistry, Govt. Vidarbha Institute of Science and Humanities, Amravati, India.
*Correspondign author E-mail: subodhvmv@gmail.com
http://dx.doi.org/10.13005/ojc/300150
(Received: December 20, 2013; Accepted: January 10, 2014)
ABSTRACT
2-acetyl-1-naphthol 2 is prepared by Modified Nenchi’s method which on treatment with
furfuraldehyde and KOH gives 1-(1-hydroxy naphthalen-2-yl)-3-(furan-2-yl) prop-2-ene-1-ones 3 in
excellent yield. The chalcone 3 when subjected to hydrazine / phenyl hydrazine/ semicarbazide
/ 2,4 dinitro phenyl hydrazine / isonicotinic acid hydrazide in DMF solvent gives 3-(1-hydroxy
naphthalene-2-yl)-5-(furan-2-yl)-1-substituted pyrazolines 4, 5, 6, 7 and 8 in 35-45% yield. The
structural assignments to the compounds 4, 5, 6, 7 and 8 are based on their elemental analysis and
spectral data.
key words: Synthesis, Characterization, Pyrazolines.
INTRODUCTION
It has been observed that substituted
flavanones are the best starting compounds for
the preparation of 4-aroyl derivatives of pyrazoline.
Present work deals with the synthesis of some new
pyrazolines and their characterization by spectral
analysis ( IR, 1H NMR )
The literature survey reveals that pyrazoline
derivatives have been studied extensively because of
their ready accessibility, diverse chemical reactivity,
broad spectrum of biological activity1-9 and variety
of Industrial applications10-12. Pyrazolines with
sulphonamidoaryl substituent at 3-position show
cerebroprotective13, antidepressant activity14, anti-
implantation activity15, hypoglycemic activity16. Due
to this vital biological roll of pyrazoline derivatives, it
was thought of interest to synthesize titled pyrazoline
derivatives . Thus we present herein the synthesis
of the titled compounds.
EXPERIMENTAL
All the melting points were taken in silicon oil
bath with open capillary tubes and are uncorrected.
1
H NMR spectra were recorded on a Brucker
AC300 FNMR spectrometer(300MHz), using TMS
as an internal standard. IR spectra were recorded
on a Nicolet-Impact 400 FT-IR spectrometer. Thin

362
BHANDARKAR, Orient. J. Chem., Vol. 30(1), 361-363 (2014)
Layer Chromatography on silica gel-G, was used to the mixture was refluxed for about 8 hours then cooled
check the purity of the compounds.Microanalysis of & poured in acidulated water. The solid obtained
nitrogen was obtained on Colman 29-N analyzer.
was filtered, washed, dried and recrystallized from
rectified spirit to obtain compound 2. Physical data
of the compound is given in table 1 .
Experimental Section
Procedure for the synthesis of 2-acetyl-1-
naphthol 2
2: IR (kBr) : 1650 (C=O), 3412 (-OH)
In hot glacial acetic acid (80ml), fused
NMR (CDCl3 + DMSO-d6) : δ 2.35
ZnCl2(50 gm) was added and refluxed till dissolved, (S,3H,CH3), δ 7.11-6.88 (m, 6H, Ar-H), ´ 9.83 (S,1H,-
then powdered 1-naphthol (30gm )was added and OH)
Table 1: Physical and analytical characterization data of newly synthesized compounds
S.
Comp ound Molecular
R
Melting
%
% Nitrogen
R.F.
No. No
formula
Point 0C Yield
Found Calculated Value
1
2
3
4
5
6
7
2
3
4
5
6
7
8
C12H10O2
C17H12O3
-
-
980C
72%
71%
38%
40%
45%
40%
35%
-
-
-
-
1260C
1100C
1000C
1400C
1200C
1170C
C17H14N2O2
C23H18N2O2
C18H15N3O3
C23H16N4O6
C23H17N3O3
H
C6H5
CONH2
C6H3N2O4
C5H4NCO
10.00
7.81
12.99
12.56
10.91
10.07
7.91
13.08
12.61
10.97
0.79
0.88
0.87
0.78
0.84
Synthesis of 1-(1-hydroxy naphthalen-2-yl)-3- product was filtered and recrystallized from ethanol
(furan-2-yl) prop-2-ene-1-one (3)
to obtain the compounds (3). The physical data is
2-acetyl-1-naphthol ( 0.01mole ) and given in Table 1
furfuraldehyde (0.02 mole) were added in ethanol
solvent (20ml). To this mixture KOH (10%, 10ml)
3: IR (KBr):1650 (C=O), 3412(-OH),
solution was added dropwise with constant stirring. 1155(C-O-C) NMR (CDCl3 + DMSO-d6) : δ 6.98-7.46
The reaction mixture was kept overnight. Then the (m,9H, Ar-H), δ 8.057 (d,1H =CH) , δ 8.099(d,1H
mixture was poured over crushed ice & little HCl. The =CH) δ 9.63 (S,1H,-OH)

BHANDARKAR, Orient. J. Chem., Vol. 30(1), 361-363 (2014)
363
Synthesis of 3 - (1-hydroxy naphthalen – 2 – yl )-5-
( furan-2-yl ) - 1-substituted pyrazolines (4-8)
1-(1-hydroxy naphthalen-2-yl)-3-(furan-
6: IR (KBr):1723 (C=O), 3405(-OH),
1160(C-O-C) NMR (CDCl3 + DMSO-d6) :δ 6.81-7.40
(m,6H, Ar-H), δ 8.041 (d,1H =CH) , δ 8.079(d,1H
=CH) δ 9.49 (S,1H,-OH), 6.6 (S,2H,NH2)
2-yl) prop-2-ene-1-ones (0.01mole) & hydrazine /
phenyl hydrazine/ semicarbazide / 2,4 dinitro phenyl
hydrazine / isonicotinic acid hydrazide (0.01 mole)
were added to DMF (20 ml ) and refluxed for 2 hours.
The cooled reaction mixture was diluted with water
& the semisolid so obtained was triturated with
ethanol to get a solid which was recrystallised from
ethanol–acetic acid mixture to get titled pyrazolines
in 45-51% yield .The physical data is given in Table
1
7:IR(KBr):1530,1550(NO2),3412(OH),
1155(C-O-C) NMR (CDCl3 + DMSO-d6) :δ 6.81-7.60
(m,9H, Ar-H), δ 8.045 (d,1H =CH) , δ 8.081(d,1H
=CH) δ 9.43 (S,1H,-OH)
8: IR (KBr):1611 (C=O), 3477(-OH),
1170(C-O-C) NMR(CDCl3 + DMSO-d6) :δ 6.95-7.81
(m,10H, Ar-H), δ 8.043 (d,1H =CH) , δ 8.083(d,1H
=CH) δ 9.50 (S,1H,-OH)
4:IR (KBr):3000 (N-H), 3402(-OH), 1151(C-
O-C) NMR (CDCl3 + DMSO-d6) : δ 6.90-7.80
(m,6H,
ACkNOWLEDGEMENTS
Ar-H), δ 8.051 (d,1H =CH), δ 8.091(d,1H =CH) δ
9.62 (S,1H,-OH)
The author is thankful to the Director,
Govt.Vidarbha Institute of Science and Humanities,
Amravati.
5: IR (KBr):1600 (C=C), 3410(-OH),
1148(C-O-C) NMR (CDCl3 + DMSO-d6) :δ 6.89-7.90
(m,11H, Ar-H), δ 8.049 (d,1H =CH) , δ 8.081(d,1H
=CH) δ 9.53 (S,1H,-OH)
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