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PROJECT TOPIC – MIZOROKI – HECK REACTION IN THE ARYLATION OF ANGULAR TRIAZAPHENOXAZINE AND THE RELATED MONOAZA

MIZOROKI – HECK REACTION IN THE ARYLATION OF ANGULAR TRIAZAPHENOXAZINE AND THE RELATED MONOAZA

 

NOTE: IT WOULD BE POSSIBLE THAT THIS SITE PROVIDES DETAILED MATERIAL ON THIS RESEARCH WORK

 

ABSTRACT

Mizoroki-Heck reaction in the arylation of angular triazaphenoxazine and the related monoaza analogue is reported. This was achieved by the reaction of 4,5-diamino-6-hydroxyl pyrimidine with 7-chloro-5,8-quinolinequinone (obtained by a multistage conversion of 8- hydroxy quinoline ) in the presence of anhydrous sodium acetate to yield 11–Amino-1,8,10-triazabenzo[a]phenoxazin-5-one. In a similar development, 2-aminophenol was reacted with 7-chloro-5,8-quinolinequinone to yield 1-azabenzo[a]phenoxazin-5-one. 11–Amino-1,8,10-triazabenzo[a]phenoxazin-5-one was subjected to the Mizoroki-Heck coupling reaction by refluxing for 4 hours with substituted iodo benzene (2-lodo benzoic acid, 1-iodo-4-nitrobenzene, and 4–iodo-phenol), using 1,4-Bis-(diphenylphosphino)butane-palladium(II)chloride as catalyst, 1,4-Bis-(2-hydroxy-3,5-ditert-butylbenzyl)piperazine as ligand and methanol as solvent at a temperature of 60–65oC to yield 6-(2-carboxyphenyl)-11-amino-1,8,10-triazabenzo[a]phenoxazin-5-one, 6-(4-nitrophenyl)-11–amino-1,8,10-triazabenzo[a]phenoxazin-5-one and 6-(4-hydroxyphenyl)-11–amino-1,8,10-triazabenzo[a]phenoxazin-5-one respectively. on the other hand 1-azabenzo[a]phenoxazin-5-one was subjected to Mizoroki-Heck coupling reaction by refluxing with substituted iodo benzene (2-iodo benzoic acid, 1-iodo-4-nitrobenzene, and 4–iodo-phenol), using 1,4-Bis (diphenylphosphino) butane-palladium (II) chloride as catalyst, 1,4-Bis-(2-hydroxy-3,5-ditert-butylbenzyl)piperazine as ligand and methanol as solvent at a temperature of 60–65oC to yield 6-(2-carboxyphenyl)-1-azabenzo[a]phenoxazin-5-one, 6-(4-nitrophenyl)-1-azabenzo[a]phenoxazin-5-one and 6-(4-hydroxyphenyl)-1-azabenzo[a]phenoxazin-5-one respectively. These structures were established by spectral analysis

 

MIZOROKI – HECK REACTION IN THE ARYLATION OF ANGULAR TRIAZAPHENOXAZINE AND THE RELATED MONOAZA

 

CHAPTER ONE

INTRODUCTION

There is a recent global demand and dependence on synthetic heterocyclic compounds for use as pesticides, herbicides, dyes, pigments, pharmaceuticals1,2 and semi products in the preparations of hexazocyclanes-fluorophores3 Phenoxazines derivatives are compounds of great interest because of their several successful applications as dyes and drugs. They exhibit strong biological activity and are extensively studied, the biological activities range from antidepressant4 antitumor5, anticancer6, antibacterial7, antituberculosis8, and schizophrenia agents.9 Among the several applications of phenoxazine derivatives are their uses as acidbase indicators10, biological stains11, laser dyes10 and especially as chromophoric compounds13 in host guest artificial protonic antenna systems. After the discovery of the parent phenoxazine ring 1, a lot of structural modifications were carried out to minimize undesirable effects12 and at the same time enhance it’s biological activities.

DIAGRAM SPACE OF NH-O

These molecular modifications had opened new areas of applications and yield derivatives such as 2, 3, 4, 5, 6 and 7.

 

SPACE FOR THE DIAGRAM OF NH-O COMPOUNDS

 

Compounds 2, 3, 4, 5 and 6 are described as “angular” phenoxazines due to the non-linear arrangement of the ring systems13, as a result of the fused rings at position a, c, h and j bonds of the phenoxazine. There are also systems in which two benzene rings are attached to two different positions on the parent compound. Such structures include dibenzo [a,i] phenoxazine 8; dibenzo [a,j] phenoxazine 9;dibenzo [a, h] phenoxazine 10.

 

MIZOROKI – HECK REACTION IN THE ARYLATION OF ANGULAR TRIAZAPHENOXAZINE AND THE RELATED MONOAZA

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