Synthesis of pyrrolyl and pyrazolyl sulfonamides

Padmavathi, V.; Swapna, M.; Reddy, S.; Padmaja, A.

doi:10.1007/s10593-013-1186-4

Cited by 3 publications

(2 citation statements)

References 17 publications

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“…Sharpless dihydroxylation of vinyl sulfones proceeds with subsequent elimination of sulfinate, and gives enantiomerically pure α‐hydroxy aldehydes, which can be further transformed, e.g., into enantiomerically and diastereomerically pure piperidines such as 16 . Styrylsulfonamides have also been used for the synthesis of pyrrole‐ and pyrazolesulfonamides (e.g., 17 ) by reaction with tosylmethyl isocyanide (Tosmic) or diazomethane, respectively (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Styrylsulfonates and ‐Sulfonamides through Pd‐Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts

2016

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Arene diazonium salts undergo Matsuda-Heck reactions with vinylsulfonates and -sulfonamides to give styrylsulfonic acid derivatives in high to excellent yields and with high to excellent selectivities. By quantifying the evolution of nitrogen over time in a gas-meter apparatus, the reactivities of ethylvinylsulfonate and the benchmark olefin methyl acrylate were compared for an electron-rich and an -deficient arene diazonium salt. Tertiary sulfonamides react in Matsuda-Heck couplings with high conversions, but require long reaction

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Section: Introductionmentioning

confidence: 99%

Styrylsulfonates and ‐Sulfonamides through Pd‐Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts

2016

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“…This transformation, which was originally developed by van Leusen et al, [63] has been widely used for the synthesis of pyrroles and other heterocycles, [64][65] but only few examples for its application to α,β-unsaturated sulfonyl compounds have been described in the literature. Padmavathi and co-workers reported the syn-thesis of pyrrole-3-sulfones [66] and pyrrole-3-sulfonamides [67] along this route.…”

Section: Resultsmentioning

confidence: 99%

Ruthenium‐Catalyzed Sulfoalkenylation of Acetanilides and Dual‐Use of the Catalyst Directing Group

Sand

Schmidt

2021

Eur J Org Chem

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In contrast to vinylsulfonates and vinylsulfones, vinylsulfonamides are unreactive in Pd‐catalyzed oxidative Heck‐coupling reactions with acetanilides. This limitation has been resolved by using a C−H‐activation protocol based on Ru−Cu−Ag‐catalysis. Overall, the Ru−Cu−Ag‐catalyzed conditions turned out to be more reliable and showed better reproducibility than the Pd‐catalyzed C−H‐activation. The coupling products thus obtained are functionalized styrenyl sulfones and –sulfonamides which can be used as starting materials for the synthesis of sulfonyl pyrroles and sulfonyl pyrrolo[2,3‐c]quinolines.

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