Journal of Basic and Applied Engineering Research
Print ISSN: 2350-0077; Online ISSN: 2350-0255; Volume 1, Number 13; October-December 2014 pp. 70-73
© Krishi Sanskriti Publications
http://www.krishisanskriti.org/jbaer.html
Greener and Efficient Synthesis of Some Novel
Substituted Azetidinones with 4-Amino Pyridine
via γ-Ferrite as a Heterogenous Catalyst
*
Ritu Yadav
1
, Kalpana Avasthi
2
and Takallum Khan
3
1,2,3
Green-Synthetic Organic Laboratory, Department of Chemistry,
Dr. Hari Singh Gour central University, SAGAR (M.P.) 470003, INDIA
E-mail:
1
rituyadav1971@yahoo.co.in,
2
kalpana.avasthi@gmail.com
Abstract—A new series of (3-chloro-2-oxo-4-substituted-Aryl-N-
pyridine-4-yl-azetidinone) β –lactams (3a-3j) were synthesized via
heterogenous catalysed reaction between 4 amino- pyridine and
substituted aromatic benzaldehyde as a starting material by
conventional in two steps. The structure of all the synthesized
compounds were confirmed by chemical and spectral analysis such
as IR,1H NMR,13C NMR and FAB-Mass.
1. INTRODUCTION
Organic synthesis promoted by a solid heterogeneous catalyst
have attracted wide spread interest and are advantageous
because of operational simplicity, high selectivity, and clean
separation of the product. Metal oxides has been recognized as
a remarkably useful green heterogeneous catalyst to promote a
wide range of organic reactions.
1
Herein we report a rapid and
green approach to achieve highly substituted Azetidinones
with pyridine in excellent yields in the presence of catalytic
amount of γ-ferrite (Fe2O3) under controlled.
Pyridine derivatives of different heterocyclic nucleus have
shown very important pharmacological properties like
antifungal
2-4
,antitubercular
5
, antibacterial
6
, antimicrobial
7
,
insecticidal
8
etc. Furthermore, different moieties of
thiadiazole
9-10
, thiazolidinone
11-12
, and azetidinone
13-14
have
also been reported to exhibit potent antifungal activities by
several scientists. In the light of these observations,
compounds of series.I were synthesized incorporating
azetidinone moieties at 4-position of pyridine nucleus with a
hope to develop better antifungal agents
15
. These compounds
have been screened for their antifungal activity. 2-Azetidines
have been extensively investigated by the organic chemists
due to their close association with various types of biological
activities
16
Azetidineones also have great importance because
of the use of β-lactam derivatives as antibacterial agents.
2. MATERIALS AND METHODS
All Melting points were taken in open glass capillaries and are
uncorrected. Progress of the reaction was monitored by TLC
on pre-coated Silica gel-aluminium plates (Type 60 F254,
Merck, Darmstadt, Germany) in MeOH:CHCl3 system (1:9).
The spot was visualized by exposing exposure to UV-light
(254 nm) or dry plate in iodine vapours. The IR spectra were
recorder on shimadzu FT-IR 8300 ( ν max in cm1)
Spectrophotometer using (KBr disc) .
1
HNMR and
13
C-NMR
spectra were measured on a JEOL DELTA-300 were
spectrometer in DMSO-d6 at 300 MHz using TMS as an
internal standard. Chemical shifts reported on δ scales. The
FAB mass spectra were recorded on a JEOL SX-102 mass
spectrometer. Elemental analyses were performed on a Carlo
Erba-1108 analyser. The analytical data of all the compounds
were highly satisfactory. For column chromatographic
purification of the products, Merck silica Gel 60 (230-400
Mesh) was used. All chemicals were purchased from Sigma-
Aldrich and the reagent grade chemicals were purchased from
commercial sources and further purified before use.
2.1 General procedure for synthesis of Schiff bases
compound ( 2a-2j)
4-Amino-pyridine (0.05 mol) was dissolved in 5 ml of ethanol
in a 250 ml conical flask and was stirred at room temperature
for 15 min to get a clear solution. To this solution, equimolar
quantity (0.05 mol) of each substituted aryl aldehydes (in
Ethanol) were added in presence of heterogenous catalyst γ-
ferrite (Fe2O3) (in catalytic amount (0.01 mole%) and
reaction mixture was refluxed with stirring up to 6–8 h at
70°C on magnetic stirrer. The reaction progress was monitored
by TLC using mobile phase as chloroform: methanol (6:4).On
completion of reaction, then allowed to cool. The product was
purified over a column chromatography. The purified product
was recrystallized from methanol at room temperature to give
compound (2a-2j : Characterisation data of compounds (2a-2j)
are presented below :