Republic of Iraq
Ministry of Higher Education
and Scientific Research
University of Thi-Qar
College of Science
SYNTHESIS AND CHARACTRAZATION OF
SOME NEW γ-LACTAM COMPOUNDS
A Thesis
Submitted to the council of the College of Science
University of Thi-Qar
In Partial Fulfillment of the Requirements
for the Master Degree of Science in Chemistry
By
Sahib Awadh Gatea Al-Jayyashee
B.Sc.Chemistry(1998)
Supervised by
Prof.Dr
Mahmood Shakir Magtoof Al-Tamemay
2015 A.D
1436 A.H
Summary
This study is concerned with the synthesis and characterization of mono-γlactams 3(a-d ) and
bis-γ-lactams 3(e-h ) , as shown in table 2 . These
compounds were prepared by reacting Phenylsuccinic anhydride
appropriate Schiff
chloroform
with the
bases (imines) 2(a-h) , as shown in table 1 by using
solvent and
heated
at temperature
(51-61˚C) in moderate
yields(70-92)% .And explained spectrum proton nuclear magnetic resonance
(1H-NMR) and nuclear magnetic resonance spectrum carbon 13 (13C-NMR)
appearance isomers of cis and trans clear where it was clear from the three
protons of the ring pyrrolidine-2-one . The general reaction of the synthesis of
mono-(E),(Z)-Gamma- Lactams 3(a-d ) and bis-(E),(Z)-Gamma-Lactams 3(e-h)
, is shown below :
The general reaction of the synthesis of Mono-E,Z-Gamma-Lactams 3(a-d)
I
The general reaction of the synthesis of Bis-E,Z-Gamma-Lactams 3(e-h)
The structures of these γ- lactams were established on the basis of the spectral
data : UV , IR , 1H-NMR ,
13
C-NMR , DEPT
NMR , Mass .
II
13
C-NMR , HSQC 1H-13C-
Table 1 : The chemical structures of prepared imines Compounds 2(a-h)
symbol
Name
Chemical Structure
2a
N-(2-chlorobenzylidene) 4chloroaniline
2b
N-(2-bromobenzylidene)-4chloroaniline
2c
2d
N-(2-bromobenzylidene)-4methylaniline
N-(2-fluorobenzylidene)-4methylaniline
III
2e
2f
N1,N4-bis(2-chlorobenzylidene)
benzene-1,4-diamine
N1,N4-bis(2-fluorobenzylidene)
benzene-1,4-diamine
2g
N1,N5-bis(2-chlorobenzylidene)
naphthalene-1,5-diamine
2h
N1,N5-bis(4-methoxybenzylidene)
naphthalene-1,5-diamine
IV
Table 2 :The chemical structures of the prepared γ- lactams Compounds 3(a-h)
symbol
3a
3b
Molecular
Formula
( Molecular
Weight)
Chemical Structure
C23H17Cl2NO3
(425)
C23H17BrClNO
3
(469)
3c
C24H20BrNO3
(449)
3d
C24H20FNO3
(389)
V
Three dimension structure
3e
C40H30Cl2N2O
6
(704)
3f
C40H30F2NO6
(672)
3g
C44H32Cl2N2O
6
(754)
3h
C46H38N2O8
(746)
VI