The aim of the present work is synthesis of new phenoxathiin derivatives. The 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) obtained from the reaction 2-acetylphenoxathiin with different aromatic aldehyde in the presence of sodium hydroxide. The reaction of 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) with hydroxylamine hydrochloride in ethanolic sodium hydroxide solution to get 2-(isoxazolin-3-yl) phenoxathiin derivatives (4a-4j) which substituted at position (5) in isoxazoline ring with different aryl groups according to aromatic aldehyde used in the preparation of (3a-3j). All the synthesized compounds were characterized by different identification techniques to confirm structure which has been obtained.

This work includes two steps of synthesis, the first one is the synthesis of indole which was prepared according to literature of the reaction of phenyl hydrazine with acetaldehyde in glacial acetic acid afforded phenyl hydrazone of acetaldehyde , this product was fused with zinc chloride to give the indole.Reaction of cyclohexanone with phenyl hydrazine using the same procedure for the preparing giving 1,2,3,4-Tetrahydrocarbazole.Second step involved synthesis of a series of (17) of mannich bases derivatives of indole and 1,2,3,4-Tetrahydrocarbazle. Mannich reaction involves the condensation of aldehyde usually formaldehyde with different secondary amine and with compound containing an activated hydrogen.The reaction illustrated by the following equation :R2NH+HCHO+RH?R2N-CH2-R+H2O These compounds were characterized by U.V , FT-IR and 1H-NMR spectra for two compounds. The secondary amines that used to prepare mannich bases are:N-methyl –N-phenyl amine, N,N-dimethyl amine, N,N- diphenyl amine, N-ethyl –N- phenyl amine, N,N-di-n-propyl amine, pyrrolidine, morpholine, N- methyl pipyridine, N,N-dibenzyl amine, N,N-di –n-butyl amine and N,N-di ethyl amine.

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.

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The aim of the present work is synthesis of new phenoxathiin derivatives. The 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) obtained from the reaction 2-acetylphenoxathiin with different aromatic aldehyde in the presence of sodium hydroxide. The reaction of 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) with hydroxylamine hydrochloride in ethanolic sodium hydroxide solution to get 2-(isoxazolin-3-yl) phenoxathiin derivatives (4a-4j) which substituted at position (5) in isoxazoline ring with different aryl groups according to aromatic aldehyde used in the preparation of (3a-3j). All the synthesized compounds were characterized by different identification techniques to confirm structure which has been obtained.