Synthesis of New Pyrazoline - Phenoxathiin Derivatives

Baghdad Science Journal

doi:10.21123/bsj.10.2.405-419

Abstract

Phenoxathiin was prepared by the reaction of diphenyl ether with sulfur in the presence of anhydrous aluminum chloride. This work comprised the synthesis of new phenoxathiin derivatives containing heterocyclic moieties. These heterocyclic compounds were synthesized in three groups. The first group was made up of 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) obtained from the reaction of 2-acetylphenoxathiin with different aromatic aldehyde in the presence of sodium hydroxide. The other two groups involved compounds produced from the reaction of (3a-3j) with hydrazine hydrate in acetic acid to get 2-(1-acetyl pyrazolin-3-yl) phenoxathiin derivatives (4a-4j), and phenyl hydrazine in the presence of piperidine to afford 2-(1-phenyl pyrazolin-3-yl) phenoxathiin derivatives (5a-5j). All these compounds of two groups above were substituted in position (5) in pyrazoline ring with different aryl groups according to aromatic aldehyde used in the preparation of the first group series compounds.

Highlights

Phenoxathiin is given as the preferred name by Patterson and Capell[1-3].Most widely method of preparation of phenoxathiinhas been used alkyl phenoxathiinoxides by Ferrario[4-10]and dioxides of cycloalkylphenoxathiins and their halogen derivatives have been recommended as modifiers in plastic materials, intermediates antioxidants and as rubber and gum inhibitors[11-13]
Oxypropen-1-yl) phenoxathiin(3a)(0.313g, 0.001 mol) in acetic acid (96%, 1 ml) hydrazine hydrate (0.4 ml, 0.008 mol) was added and the mixture was refluxed for 5 hrs., the product separated and out on cooling was crystallized from (3:1) to give (4a), the following compounds were prepared in this manner
Table (5) represent the physical data of compounds(5a-5j).Characteristic bands ofFT-IRspectra of compounds (5a-5j) are listed in Table (6).Results and Discussion: Phenoxathiin reacted with acetyl chloride in dry carbon disulfide in presence of anhydrous aluminum chloride to get 2-acetyl phenoxathiinthroughFriedel Crafts acylation method

Summary

Introduction

Phenoxathiin is given as the preferred name by Patterson and Capell[1-3]. Most widely method of preparation of phenoxathiinhas been used alkyl phenoxathiinoxides by Ferrario[4-. Alkylated phenoxathiin has excellent oxidative stability and excellent anti-wear properties, so they are beneficial as lubricant additives, lubricant base stocks, or intermediates to lubricant base stock to improve viscosity and wear properties [15]. In biological field, they are used in many drugs as bacteriostatic, fungicides, anthelmintic, insecticides and antiviral agents such as distemper virus, influenza virus, hepatitis virus, neurotropic virus and especially influenza and herpetic viruses [16]. The phenoxathiin and its derivatives are used subunits to prepared different compounds exampledihydroazulenes(DHAS)[17]. Organometallic derivatives of phenoxathiin have been prepared with different elements such as lithium and silicon [21-31]

Materials and Methods

Part Two

Part Three

Discussion

Findings

A Comparison of the Directive