International Research Journal of Innovations in Chemistry (IRJIC) Vol. 01, Issue 02, 05-07 (2014)
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International Research Journal of Innovations in Chemistry
(IRJIC)
AN INTERNATIONAL PEER REVIEWED MONTHLY JOURNAL
Published by
International Union for Scientific Education and Research
(IUSER)
ISSN : 2348-3199
Available online at www.iuserinfo.com
Original Article:
Synthesis and Characterization of Some New Derivatives of Schiff’s Bases
*Mangesh Kadu
*Department of Applied Chemistry, Anuradha Engineering College,Chikhli – 443201 (India)
A B S T R A C T:
The
present work deals with the synthesis and characterization of some new
derivatives of Schiff’s bases. In this synthesis p-nitro aniline was reflux with
substituted aldehydes in presence of 2-3 drops of conc. sulphuric acid in ethanol. The
characterization and structural determination was done by elemental analysis, chemical
reactions and spectral data.
A R T I C L E I N F O:
Article history:
Received 15 August 2014
Accepted 23 August 2014
Available online 01 October
2014
………………………………
Keywords:
p-nitro aniline
Substituted aldehydes
*Corresponding Author. Department of Applied Chemistry, Anuradha Engineering College, Chikhli-443201 (MS),India Tel.: +91 9822948035,
E-Mail Addresses [email protected] (Mangesh Kadu), Available Online at www.iuserinfo.com,
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1. Introduction:
Schiff’s bases have been synthesized by the
condensation
of
aniline
with
substituted
benzaldehyde which shown to have anticancer
activities [1]. Benzaldehyde-2 hydroxxy aniline was
prepared by the condensation of o-aninophenol with
substituted benzaldehyde in ethanol in presence of
2,3 drops of conc. H2SO4 [2]. Benzioxazoles were
prepared by the cyclization of ortho N-diacetyl
derivative of o-amionphenol at lower temperature by
treating aminophenol with carboxylic acid or its
derivative [3]. It was suggested this azomethine
linkage might be responsible for biological activities
5
Mangesh Kadu
of Sciff’s bases [4]. Some oxime derivatives having
ethoxy group have been reported to possess
antiinflammattory activities [5]. Some 2-oxothiazine
hydrazones from 3-methoxy, allyloxy benzaldehyde
are endowed with anti-HIV activities [6]. Some new
2-thiophenylidine substituted aniline was prepared by
known method [7]. Some new azo Schiff’s bases
have been synthesized by the reacting of 5-pmethoxyphenylazo salicyldehyde with primary
aromatic amines [8]. The substituted phenolic azo
Schiff bases, i.e., 2-hydroxy-5-(4-nitrophenylazo)
benzaldehyde with substituted aniline [9]. Some
Schiff’s bases of 2-amino-3-(N-Tolyl carboxamido)-
International Research Journal of Innovations in Chemistry (IRJIC) Vol. 01, Issue 02, 05-07 (2014)
4,5,6,7-tetrahydro
benzo(b)
thiophenes
were
synthesized and tested for antibacterial activities [10],
a-pyrano chalcones and related compounds were
synthesized from 3-acetyl umbelliferone and tested
for anti-inflammatory activities [11]. Antimicrobial
activities
of
1-(2-benzoyl-6-hydroxy-3methylbenzofuron-5-yl)-3-aryl propenones were
studied [12-13]. Schiff’s bases were synthesized from
fluorinated chalcones [14] and 2-methoxy-4, 6dimethoxy-methoxy acetophenones and tested for
antimicrobial activities [15].
2. Experimental:
Synthesis of schiff’s bases (Ia-i):
Com
poun
d
Ia
Ib
Ic
Id
Ie
If
Ig
Ih
Ii
P.aeru
ginosa
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S.
aureus
C.
E.
P.
B.
frundi
coli
mirabi
megatheri
i
lis
um
7
6
8
6
5
7
8
9
8
7
6
5
5
4
5
6
7
8
5
6
5
7
5
6
5
6
7
6
6
6
7
6
6
6
6
6
8
7
8
7
7
7
6
7
8
8
8
7
8
7
7
7
8
7
Table-1: Antimicrobial activities of synthesized compounds
(Strongly active range: >12mm, moderately active range: 8-12mm,
weakly active range <8mm.)
References:
A mixture of p-nitro aniline and substituted
aldehydes in 1:1 ratio was reflux in ethanol in
containing few drops of conc. sulphuric acid for half
an hour. The reaction mixture was neutralized by
sodiumbicorbonate to obtain shift bases (Ia-i).
1.
Pobb, F.D., J Org. Chem., 26,566 (1966).
2.
Lokhande, P.D. and Ghirya B.J., J.Indian
Chem Soc., 68, 412 (1991).
3.
Masnow, T., Masaleo and K. Vulch,
Synthesis, 6,434(1982).
3. Results and discussion:
4.
3.1 Antimicrobial activities of synthesized
compoundses (Ia-i):
Shridhar, D.R., Vishwakarma, L.C. and Rao
S.B., J.Ind.Chem.Soc., 56, 84 (1979).
5.
In case of antimicrobial activity from table-2 it has
been observed that all the compound ( Ia-i) showed
moderate activities against P. aeruginosa, S. aureus ,
C. frundii, E. Coli, P. mirabilis, B. megatherium and
S. typhi.
Singh, A.K. and Rastogi S., Indian J.Chem.,
32b, 738 (1993).
6.
Jolly, V.S. and Sharma K.P., J. Ind Chem
Soc., 67412 (1990).
7.
Idrees, M.D., Siddique, M.D., Doshi, A.G.
3.2Spectral data of compound Ia
and Raut A.W., Oriental J. Chem., 17(1),
IR(KBr): (V max) 1350 cm-1(C-N stretching); 1550
cm-1(NO2 stretching); 845 cm-1(C-N); 900-860 cm1
(C-H);1585-1570 cm-1 (C-O).
143- (2001).
8.
Halve Anand, and Abha Goel, Oriental J.
Chem., 12, 87 (1996).
NMR: δ 2.47(s, 3H, -CH2); δ 6.25(s, 1H, -CH=N); δ
7.3 (d, 1H, Ar-NO2-H); δ 7.4 to8.8 (m,7H,Ar-H);
9.
Raut, A.W., Doshi, A.G. and Jadho S.T. ,
Asian J. Chem., 12(2), 619-620 (2000).
UV (λmax): 280 nm
10. Mohan, S. and Suravanan J., Asian J. Chem.
R6
R1
Vol. 15, No.1, 67-70 (2003).
R5
11. Khan, V. and Bawa S., Indian J. Chem.,
R2
CHO
R4
H2N
EtOH/Reflux
40B, 207 (2001).
Conc.H2SO4
12. Ram, B., Balram, B., Subhada, J., Rajita, B.
Substituted aniline
R3
R1
R6
and Rao K., Ind. J. Hetero. Chem., 40B, 120
R5
(2001).
Substituted aldehyde
R2
C
H
R3
Scheme 1: Synthesis of Ia-f
7
Mangesh Kadu
N
Schiffs base
IIa-f
R4
13. Ratna Kumari, V., Sarada, J., Rajita, B. and
Rao K., Ind. J. Hetero. Chem., 13(1), 89
(2003).
S.
typhi
9
8
5
6
6
6
8
7
7
International Research Journal of Innovations in Chemistry (IRJIC) Vol. 01, Issue 02, 05-07 (2014)
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14. Nandela, Rama Rao, Asoam J. Chem.,
16(1), 525 (2004).
15. Alam, Sayed and Azizul, Islam, Acta
Ciencia Indica, XXIV C (2), 83 (2003).
***
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Mangesh Kadu