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  carbocyclic analogue  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.
cÂŁH ;
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
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