ABSTRACT
Synthesis of twelve O-arylated diazabenzo[a]phenoxazine-5-one and its carbocyclic analogue is reported in 46 – 99 % yields. The intermediates were prepared by anhydrous base catalyzed reaction of 2,3-dichloro-1,4- naphthoquinone with 4,5-diamino-6-hydroxyl-2-mercaptopyrimidine and 2- aminophenol. The O-arylation process occurred smoothly in non-polar solvent, toluene with the inexpensive base, KPO, at 110C. The intermediates were combined with a variety of electron-deficient, electrically neutral and electron-rich phenols in the presence of a catalyst combination of Pd(OAc)» and electron rich, bulky alkyldiary/phosphine ligand in which the alkyl groups are tert-butyl (t-Buxphos), to furnish the arylated compounds. Bulky yet basic nature of the phosphine ligand is thought to be responsible for these transformations. The highest yields were obtained when the intermediates coupled with electron rich phenols, with the carbocyclicanalogue giving better yields. IR, ‘H NMR and ‘C NMR spectra data, confirmed the structures of all the synthesized compounds. The effect of the synthesized compounds on bacteria and fungi growth was studied. The studied compounds were found to be potent antibacterial and antifungal agents as they showed significant biological activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Candida albicans. In addition, they may be useful as dyes in industries since they absorb in the UV- visible region.
1.0 INTRODUCTION
CHAPTER ONE
1.1 BACKGROUND OF STUDY:
Angular phenoxazines are defined as the polynuclear phenoxazines that have non-linear arrangement ring system’. Angular phenoxazines and its aza analogues constitute important classes of organic compounds because of their wide range of commercial uses. They are used as dyes 1 and drugs. They exhibit
strong biological activities rangmg from antidepressant,
ant1. tumour4,
anticancer, antibacterial, and antituberculosis’ and schizophrenia agents’. Among the several industrial applications of angular phenoxazine derivatives are their use as acid-base indicator’, biological stains”, laser dyes” and chromophoric compounds’.
The report of the basic structure of the parent phenoxazine I prompted the synthesis of several hundreds of derivatives, not only to improve their usefulness but also to open up new area of applications.
c£H ;
1
These structural modifications have given rise to benzo[a]phenoxazine 2,
benzo[c]phenoxazines 3, benzo[b]phenoxazine 4, benzou]phenoxazine 5,
benzo[i]phenoxazine 6 and benzo[h]phenoxazine 7″ among others. These are all
carbocyclic phenoxazines.
Structures 4 and 6 are linear phenoxazines while structures 2, 3, and 5 are angular phenoxazines.
Phenoxazine compounds that have two benzo groups attached to phenoxazine nucleus are called dibenzophenoxazines. These include compounds8, 9, and 10.
This material content is developed to serve as a GUIDE for students to conduct academic research
O-ARYLATION OF ANGULAR DIAZAPHENOXAZINE AND RELATED CARBOCYCLIC ANALOGUE USING BUCHWALD CATALYST
Project 4Topics Support Team Are Always (24/7) Online To Help You With Your Project
Chat Us on WhatsApp » 09132600555
DO YOU NEED CLARIFICATION? CALL OUR HELP DESK:
09132600555 (Country Code: +234)
YOU CAN REACH OUR SUPPORT TEAM VIA MAIL: [email protected]
09132600555 (Country Code: +234)