WORLD JOURNAL OF PHARMACY AND PHARMACEUTICAL SCIENCES
Dutta et al.
World Journal of Pharmacy and Pharmaceutical Sciences
SJIF Impact Factor 2.786
Volume 4, Issue 01, 1591-1597.
Research Article
ISSN 2278 – 4357
SYNTHESIS AND CHARACTERIZATION OF SOME BROMO
SUBSTITUTED CHALCONE BY THE GREEN SYNTHESIS WAY
(GRINDING METHOD) AND AURONES 2-BENZYLIDINE-1BENZOFURAN-3-ONE BY CYCLIZATION METHOD.
Miss Kavita P. Kakade*, Miss Sarita P.Kakade and Miss. Shubhangi Y. Deshmukh
Bar. R.D .I.K & N.K.D College of Badnera, GVISH Amravati , Vidhybharti Mahavidyalaya
Amravati.
Article Received on
17 Nov 2014,
Revised on 09 Dec 2014,
Accepted on 30 Dec 2014
ABSTRACT
The presented aurones were synthesized by cyclization of chalcones
which are prepaired from 2- hydroxy 5- bromo acetophenone and
different aldehydes a series of bromo substituted aurones were
*Correspondence for
synthesized and characterized through NMR, IR, and elemental
Author
analysis. The synthetic methods used proved successful synthesis of
Miss Kavita P. Kakade
the desired compound.Grinding technique is used to follow the green
Bar. R.D .I.K & N.K.D
College Of Badnera,
synthesis way for the synthesis of chalcone.
GVISH Amravati ,
Vidhybharti
Mahavidyalaya, Amravati.
KEYWORDS: Chalcones, Aurones, Green Synthesis (Grinding
Technique).
INTRODUCTION
kavitakakade40@gmail.co
Aurones are the important type of flavanoid, responsible for the bright yellow colour of
m
flower[1] Previous studies have shown that aurones exhibit anti-cancer activity as well as a
kavitakakade40@gmail.co
variety of other pharmacological activities, including anti-inflammatory[6-10] and anti-viral
m
properties. More specifically, these studies indicate that aurones show potential in inhibiting
cyclooxygenase-2 activity (COX-2), which plays an integral part of inflammation and its
associated diseases, such as cancer.[2-5] Furthermore, structure-activity studies have shown
that halogen substituentsincrease anti-cancer activities of flavonoidderivatives. Therefore, the
evaluation of the “A” ring halogen substituted aurone is of great importance.
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EXPERIMENTAL SECTION
SYNTHESIS OF CHALCONE
The chalcones were synthesized by using 5-bromo 2- hydroxy acetophenone with some
aldehydes (anisaldehyde, furfuraldehyde, bezaldehyde, cinnamaldehyde, salysilaldehyde )
under alkaline condition. The chalcones were obtained yellow to brown in colour their
synthesis were confirm by melting point method and from spectral interpretation. This is the
general claisen Schmidt reaction
[23]
but I use the reaction by grinding was carried out in a
mortar and pestle at room temperature. During the grinding,sudden change in color took
place, indicating the progress of reaction. The full conversion of the reaction mixture to a
solid mass indicates the completion of reaction.
General procedure
A mixture of 5-bromo 2- hydroxy acetophenone (4 mmol), aryl aldehyde (4.1 mmol) and
ammonium bromide and ammonium persulphate moist with few drops of water
[25]
is ground
at room temperature for 25 minutes in a mortar and pestle. The reaction mixture is allowed to
stand for 25 min. Then Ice-cold water (30 ml) was added to the reaction mixture and acidified
with conc. HCl. The product was collected by vacuum filtration and then recrystallized from
ethanol. The same procedure of grinding was apply by using anhydrous bariun hydroxide and
then result of two procedure was compaired.
RESULTS AND DISCUSSION
Chalcone of Benzaldehyde with ketone (C1)
OH
OH
Ba(OH)2
OR
+
O
NH4-Br( NH4)2S2O8
Br
CHO
Br
O
CH3
Chalcone of cinnamaldehyde with ketone(C2)
OH
OH
O
+
CHO
Br
Ba(OH)2
OR
NH4-Br( NH4)2S2O8
Br
O
CH3
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Chalcones of furfuraldehyde with ketone (C3)
OH
OH
Ba(OH)2
O
OR
+
CHO
O
NH4-Br( NH4)2S2O8
Br
Br
O
O
CH3
chalcone of salisylaldehyde with ketone (C4)
OH
OH
OH
OH
Ba(OH)2
O
+
OR
NH4-Br( NH4)2S2O8
CHO
Br
Br
O
CH3
Chalcone of anisaldehyde with ketone (C5)
OH
O.CH3
O.CH3
OH
O
+
Ba(OH)2
H
OR
NH4-Br( NH4)2S2O8
Br
3HC
Br
O
O
The time duration for the formation of chalcone taken by both reagent was near about
same but the yield obtained from barium hydroxide was superior than the ammonium
bromide and ammonium persulphate.
Synthesis of Aurones from chalcones: about 3.35 gm (0.01 M) of chalcones , 2.35 gm of
(0.01M) mercuric chloride , 20 ml of DMSO in round bottom flask. Reflux the reaction
mixture for 3 hours, then reaction mixture was hydrolysed by using acidified ice cold water ,
filter the crude product and wash it 3-4 times by distilled water, dried, and crystallized by
ethanol, solid product was obtained i.e aurone .
Auone of Anisaldehyde (A1)
OH
O
OCH3
DMSO,Hg(OAc)2
Br
Br
O
O
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OCH3
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auone of benzaldehyde (A2)
OH
O
DMSO,Hg(OAc)2
Br
Br
O
O
Aurone of cinnamaldehyde (A3)
OH
O
DMSO,Hg(OAc)2
Br
Br
O
O
Aurone of furfuraldehyde (A4)
OH
O
DMSO,Hg(OAc)2
Br
O
Br
O
O
O
Aurone of salisylaladehyde(A5)
OH
OH
O
DMSO,Hg(OAc)2
Br
Br
O
O
OH
Instrumentation
Table 1: Physical data of chalcones (melting point & colour)
Sr.NO
Symbol
1
C1
2
C2
3
C3
4
C4
5
C5
Name of compound
5-bromo2-hydroxy(1,3)diphenyl-2 propen-1
one
5-bromo2-hydroxy(1,5)diphenyl-2 ,4 -butadien1 one
5-bromo2-hydroxy-3furan 1-phenyl -2 propen1 one
5-bromo2-hydroxy 4 hydroxy (1,3)diphenyl-2
propen-1 one
5-bromo2-hydroxy 4- methoxy (1,3)diphenyl-2
propen-1 one
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Melting point
Colour
810c
Brown
800c
yellow
790c
Yellowish
brown
Greenish
yellow
1290c
820c
Golden yellow
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Table 2: Physical data of substituted benzofuran i.e. aurone ( melting point & colour )
Sr.no
Symbol
1
A1
2
A2
3
A3
4
A4
5
A5
Melting
point
Name
5- bromo 4- methoxy 2-Benzylidene-1-benzofuran3-one
5- bromo 2-Benzylidene-1-benzofuran-3-one
5- bromo(1,3)butadiene- 3-Benzylidene-1benzofuran-3-one
5- bromo 2-furane -1-benzofuran-3-one
5- bromo 4-hydroxy -2-Benzylidene-1-benzofuran-3one
Colour
89 oc
Greenish yellow
95 oc
Greenish yellow
o
88 c
Golden yellow
102 oc
yellow
85 oc
Yellowish brown
Infra-red spectroscopy
Table 3: The IR spectral analysis of compound showed the presence of following
absorption bands
V
Name of
(C=O)cm-1
compound
Cyclic
Sr.
no
V(c-oc)cm1
V(c=c)
cm1
aliphatic
V(-Br) cm1
Para
substituted
1
A-1
1692
1302
1636
694
2
A-2
1681
1274
1640
700
3
A-3
1694
1216
1636
684
4
A-4
1690
1019
1641
628
5
A- 5
1636
1306
1670
664
Any
special
substituent
V –OCH3
2835
V(c=c) cm1
Aromatic
-
1596
1636
conjugated
diene
1208 furan
ring –O3236 (-OH)
1562
1556
1579
1598
Table 4: The H1 NMR spectral analysis of compound showed the presence of following
absorption bands
Sr.
no
Name of
compound
(δ ppm)
No.of potons
assingment
1
A-1
3.33,7.6
7.84, 3.8 ,8.36 ,8.37
2
A-2
7.13, 3.24, 8.17
3H ,1H
1H,1H
1H,1H
1H
1H, 1H, 1H,
3
A-3
7.16, 2.5, 8.14
1H, 1H, 1H,
Ar-H, C=C-H, Br-Ar-H
4
A-4
1H, 1H, 1H, 1H
5
A- 5
6.64, 3.3260 8.21, 8.07
5.80, 7.44, 3.32
8.210
Ar-H Ar-H, , Ar-H, Br-Ar-H
Ar-O-H, Ar-H, C=C-H
, Br-Ar-H
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1H, 1H, 1H, 1H
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Ar-O-CH3, Ar-H
Ar-H, C=C-H, Br-Ar-H, Br-Ar-H
Ar-H, C=C-H, Br-Ar-H
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As the aurones are responsible for the bright yellow colour of flower thus attempt has been
made to see the effect on the flower of white colour is they show colour change . for this
Catharanthus roseus plant was selected but no significant change of colour was obtained .
CONCLUSION
The compound i.e substituted benzofuran was succesfuly synthesized by the green synthesis
way , the yield obtained was good their puriety and conformation was checked by melting
point and from spectral data .
ACKNOWLEDGEMENTS
I hearby very thankful to my friend Mr. swapnil k. warkhade who help me for this work.
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