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Syntheses of Diaryl Sulfone. IV

Takao Takubo, Tomonori Tadaoka, TOSHI SAWAI

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Abstract

As a part of work on the synthesis of chemotherapeutics, diaryl sulfones were prepared. Compounds of bis (4-aminophenyl) sulfone system included bis (4-nicotinamidophenyl), bis [4-(2-hydroxy-1-naphthylazo) phenyl], bis (2-aminobenzothiazol-6-yl), bis (4-maleylamidophenyl), bis (4-succinylamidophenyl), and bis (4-phthalylamidophenyl) sulfones. Those of bis [4-hydrazinophenyl) sulfone series included bis (4-furfurylidenehydrazinophenyl), bis [4-(3-methoxy-4-hydroxybenzylidenehydrazino) phenyl], bis [4-piperonylidenehydrazinophenyl], bis (4-cinnamylidenehydrazinophenyl), and bis [4-(4-dimethylaminobenzylidenehydrazino) phenyl] sulfones. 2-Lepidyl 4-nitrophenyl sulfone and bis (2-hydroxy-3, 5-dichlorophenyl) sulfoxide were also prepared. This latter was assumed to have been formed by the steric hindrance of hydroxyl group in the ortho position, oxidation to the sulfone not having been effected.

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As a part of work on the synthesis of chemotherapeutics, diaryl sulfones were prepared. Compounds of bis (4-aminophenyl) sulfone system included bis (4-nicotinamidophenyl), bis [4-(2-hydroxy-1-naphthylazo) phenyl], bis (2-aminobenzothiazol-6-yl), bis (4-maleylamidophenyl), bis (4-succinylamidophenyl), and bis (4-phthalylamidophenyl) sulfones. Those of bis [4-hydrazinophenyl) sulfone series included bis (4-furfurylidenehydrazinophenyl), bis [4-(3-methoxy-4-hydroxybenzylidenehydrazino) phenyl], bis [4-piperonylidenehydrazinophenyl], bis (4-cinnamylidenehydrazinophenyl), and bis [4-(4-dimethylaminobenzylidenehydrazino) phenyl] sulfones. 2-Lepidyl 4-nitrophenyl sulfone and bis (2-hydroxy-3, 5-dichlorophenyl) sulfoxide were also prepared. This latter was assumed to have been formed by the steric hindrance of hydroxyl group in the ortho position, oxidation to the sulfone not having been effected.

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Available abstract

As a part of work on the synthesis of chemotherapeutics, diaryl sulfones were prepared. Compounds of bis (4-aminophenyl) sulfone system included bis (4-nicotinamidophenyl), bis [4-(2-hydroxy-1-naphthylazo) phenyl], bis (2-aminobenzothiazol-6-yl), bis (4-maleylamidophenyl), bis (4-succinylamidophenyl), and bis (4-phthalylamidophenyl) sulfones. Those of bis [4-hydrazinophenyl) sulfone series included bis (4-furfurylidenehydrazinophenyl), bis [4-(3-methoxy-4-hydroxybenzylidenehydrazino) phenyl], bis [4-piperonylidenehydrazinophenyl], bis (4-cinnamylidenehydrazinophenyl), and bis [4-(4-dimethylaminobenzylidenehydrazino) phenyl] sulfones. 2-Lepidyl 4-nitrophenyl sulfone and bis (2-hydroxy-3, 5-dichlorophenyl) sulfoxide were also prepared. This latter was assumed to have been formed by the steric hindrance of hydroxyl group in the ortho position, oxidation to the sulfone not having been effected.

Key concepts: Sulfone, Sulfoxide, Chemistry, Steric effects, Medicinal chemistry, Organic chemistry

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