Dr vibha bhagat PHD synopsis

1. STUDIES OF OXAZOLE , BENZIMIDAZOLE, OXADIAZOLE AND
RELATED COMPOUNDS
THESIS SUBMITTED TO THE UNIVERSITY OF MUMBAI
FOR THE DEGREE OF DOCTOR OF PHILOSOPHY
FACULTY OF SCIENCE (ORGANIC CHEMISTRY)
PATKAR COLLEGE
2008

2.  SYNOPSIS
 OF THE THESIS TO BE SUBMITTED TO
 THE UNIVERSITY OF MUMBAI
 FOR THE DEGREE OF DOCTOR OF PHYLOSOPHY IN THE FACULTY
OF SCIENCE (ORGANIC CHEMISTRY)

 NAME OF THE STUDENT : VIBHA JAGDEVPRASAD PANDEY
 TITLE OF THESIS :“STUDIES IN
OXAZOLE, IMIDAZOLE, BENZIMIDAZOLE AND RELATED
COMPOUNDS”.
 NAME AND DESIGNATION : Dr.UDAY C. MASHELKAR M.Sc. Ph.D.
 THE OF GUIDING TEACHER PRINCIPAL, PATKAR
COLLEGE, GOREGAON (W)
 PLACE OF RESEARCH : ORGANIC RESAERCH LABORTORY.
PATKAR COLLEGE, GOREGOAN (W).
 NUMBER AND DATE OF : 17 / 6th DECEMBER 2005
 REGISTRATION
 DATE OF SUBMISSION OF : 20th DECEMBER 2007

4.  Compounds based on coumarin and chromone ring system
are one of the most extensively investigated and
commercially significant groups of organic compounds. In
recent years coumarin containing crown ethers and
macrocyclic systems has been exploited in the area of metal
ion sensors1 and number of these product shows marked
physiological impact2. In addition coumarins are also of
considerable biological and medicinal interest. It is found
that coumarin plays important role in enzymatic oxidation3
and shows antioxidative, perioxidative effect4.


5.  Nitrogen containing heterocycles being another important group of
heterocycles5, these compounds are widely distributed in nature. These
compounds playing a vital role in the metabolic activity of all living
cells e.g. the pyrimidine and purine bases of the genetic materials; the
essential amino acids; the vitamins and coenzymes. Imidazole and
benzimidazole are the important group of compounds6.
Benzimidazoles are known to have varied biological activity and among
them 2- substituted benzimidazolees are found to be more potent.7
 Owing to the importance of these systems in
pharmacological, commercial, analytical and industrial applications;
it’s significant to design and synthesize novel heterocycles of these
classes. Keeping this in mind, we targeted to synthesize coumarin with
benzimidazole, benzisooxazole, oxazole and oxodiazole as substitution
at four position of coumarin. At the same time these substitutions were
attached with chromone ring. As wide application of chromone and
coumarin were seen in the host-guest chemistry and metal ions
sensors8. We synthesized some of the coumarin and chromone based
podands and their complexes with transition metal ions. Podands are
linear multidentate legands. These podands are similar to salen and
smdpt9.

 The synthetic strategy employed for the purpose is summarized below.

6.  Chromone aldehyde and coumarin aldehydes were prepared as per the
literature10, from phenols by Pechmann condensation and Vilsmeier-Hack
reaction11.
 These aldehydes were condensed with hydrazides of isooxazole 2-acetic acid
esters, and subsequent cyclization in acidic medium gives the desired
oxadiazole derivatives.
 Another synthetic route employed the alkylation of imidazole with
chloroethylacetate their hydrazide formation.
 Furthermore the podands were prepared from Ethylenediamine and o-
phynelenediamine (OPDA) to yield salen and smdpt type of compound.
Complexes of these ligands with transition metal ions were studied.
 This work is presented through five chapters.

7.  Chapter one is introductory in nature dealing with
coumarins, imidazoles, isooxazoles and oxadiazoles, their general
method of synthesis, characterization and reactions that lead to
modified and highly functionalized compounds, their applications in
various fields of interest.
 Chapter two and three deals with theoretical and experimental
part of synthesis leading to coumarin and chromone derivatives with
imidazole, oxazole, oxadiazole.
 Chapter four is about the tweezers and ligands synthesis of
benzimidazole, oxazole and chromene.
 Chapter five is regarding the application part of synthesized molecule
i.e. complexation studies of the ligands with transition metals and their
biological activity.

8. O
OH OH
R
R
O O
(1)
N
O N
H
R R
O O O O (3)
(2)
Scheme-1

9. N N N
N N N H
H O N NH
2
R R O R O
O O O O O O
(3)
N
N
N
N N H
N N N
R O
O O R O
O O
R,
(4)
R,
Scheme-2

10. O
O O R
O R O
R
O O
(3)
+ N N
O
OH O O N O
N
H
O
(5)
R,
Scheme-3

11. O
OH
N
O
N N N
O O
N N N
H H H
N N N
O O O
(6) (7) (8)
Scheme-4

12. N N
N
N N
N
H
N O
N N O
O O
O HN
(6) O NH2
N N
N N
R
R N O
N N
O N O
O HN
N
O
O
(9) O
O
Scheme-5

13. O O O
OH O NH2
NH
N N
O N
O O
R
N N
O
O O
O
O N
N N O
H
O N
R O
(10)
Scheme-6

14. OH
HO O O AcO O O
HO
O
HO O O
HO O O
O
O
O O O O O
O O O
O O O O O O O
O
O
(13) (14)
(11) (12)
OH OH O
O
O
HO HO
HO
(15)
O O
O
HO
(16)
Scheme-7

15. O
O
N O O
NH O
+ O
O O O
NH N
O
[(11), (2), (14), (16)] O O O
(17)
O O O
O
N
NH O O O
O
+ O N
NH O
O
[(11), (2), (14), (16)]
(18)
Scheme- 8

16. REFERENCES:
 Valeur B. Habib Jivan J.L. J. Photoch. Photobio. A 116, 127,(1998).
 Miyake. Joshi. J. Agri. Food. Chem. 48(8), 3151, (1999).
 Swain C. G., Thripathy P. C., Ind. J. Plant. Physiology. I4(3), (1999), 157.
 Liu Z. Q., Yu. W., Chem. Phy. Lipids, 103(1,2), 125 (1999).
 Grimmet. M. R, “Comprehensive Heterocyclic
Chemistry”, Potts.K.T.(Ed), Katrizky. A.R. & Rees. K. W.(Gen.Eds.), Pergamon
Press, Oxford, Vol.5, Chapter 4, 457, (1984).
 Preston P. N. Chem. Rev., 74, 279, (1974).
 Preston P. N (ED) “Benzimidazoles and Congeneric Tricyclic
Compounds”, (Wiley Interscience, New York) Part2, Chapter 10, 531 (1980).
 a) Willem. Verboom David N. Reinhoudt, Chem. Soc. Perkin. Tran 2. 135 (1995).
b) Tyagi et.al. I.J.C. vol.78, 251 (2001).
 Ind. Ac. Sci. A. 567 (1938).
 Sethna. Sm, Shah R.C. J. Chem. Soc. 228., (1938).
 Horning, E. C. in Organic synthesis, Vol. III, Wiley, New York, 281(1955).

17. Thanks
 vibhagreat2007@gmail.com
 Tel 9322191450