Mechanistic insight into thermal 1,3- and 1,5-sulfonyl migrations of N-arenesulfonylphenothiazines and N-arenesulfonylphenoxazines

Wang, Jiandong; Son, Kwon-Il; Xu, Jiaxi

doi:10.1007/s00706-016-1661-6

Cited by 11 publications

(2 citation statements)

References 49 publications

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“…Sulfonamide synthesis using secondary amineslike Nmethyl aniline or diphenyl aniline (scheme 9) was synthesized by [56] The aim of the study was to explore the hemolytic cleavage and intermolecular radical-radical coupling reaction mechanism of 1,3and 1,5-sulfonyl migration of N-arenesulfonyl phenothiazines and N-arenesulfonylphenoxazines. Excellent yield (97%) was achieved using pyridine as a base in chlorinated solvent by portion wise adding of benzenesulfonyl chloride.…”

Section: Scheme 8; Synthesis Of Sulfonamides Using 1-phenyl Sulfonyl mentioning

confidence: 99%

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

et al. 2020

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This review spotlights on sulfonamides from different sides, including history, structure-activity relationship, chemistry, methods of classification and up to date ways for their synthesis. Moreover, the review includes a discussion of the varied pharmacological effects of sulfonamides. Sulfonamides have a good range of pharmacological activities like oral diuretics (furosemide, indapamide, chlorthalidone, thiazides); anticancer (E7070), carbonic anhydrase (CA) inhibitors (CAIs) (acetazolamide, dichlorophenamide, dorzolamide and brinzolamide), antiepileptics (zonisamide and sulthiame), for rheumatoid arthritis (Sulfasalazine) antiviral (Darunavir) anti-inflammatory (celecoxib), antibacterial (Sulfadizine), as ophthamologicals (Dorzolamide) anticonvulsant (Zonisamide) cycloxygenase 2 (COX2) inhibitors (valdecoxib). These days, novel pills are launched, like apricoxib and pazopanib, which additionally include this organization. The sulfonamides competitively inhibit vitamin Bc synthesis in microorganisms and subsequently inhibit multiplication of bacteria but donot actively kill them. They need been used against most gram-positive and lots of gram-negative bacteria, also as some fungi.

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Section: Scheme 8; Synthesis Of Sulfonamides Using 1-phenyl Sulfonyl mentioning

confidence: 99%

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

et al. 2020

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“…In addition, 1,n- N - to N - and 1,n- N - to O -migrations of the sulfonyl group through N–S bond cleavage of sulfonamide have been described . Although HX-promoted, base-promoted, Lewis acid-catalyzed, and Lewis base-catalyzed sulfonyl migrations have been demonstrated, thermally induced migrations of sulfonyl groups have been scarcely investigated . Additionally, a closer look at these 1,n-migrations of the arylsulfonyl group reveals that most reports are limited to single-component reactions involving alkyne cyclization .…”

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confidence: 99%