Iron-catalyzed synthesis of arylsulfinates through radical coupling reaction
A novel strategy for installation of a sulfonyl fragment into arenes has been accomplished via an iron-catalyzed radical coupling reaction. Arene radicals derived from diaryliodoniums via single electron transfer reaction combine with sulfoxylate anion radicals readily generated from commercially available rongalite (HOCH2SO2Na·2H2O) to afford arylsulfinates efficiently at room temperature. In this protocol, a broad range of functional groups are tolerated to give products in good yields.
Zhang, Weixi,Luo, Meiming
p. 2980 - 2983
(2016/02/19)
Copper-mediated S-N formation via an oxygen-activated radical process: A new synthesis method for sulfonamides
Copper-mediated direct S-N formation using readily available starting materials via an oxygen-activated radical process has been developed. This method provides a novel and direct approach for synthesis of sulfonamides under air conditions. the Partner Organisations 2014.
Discovery of a novel sulfonamide-pyrazolopiperidine series as potent and Efficacious γ-Secretase Inhibitors
Discovery of a series of pyrazolopiperidine sulfonamide based γ-secretase inhibitors and its SAR evolution is described. Significant increases in APP potency on the pyrazolopiperidine scaffold over the original N-bicyclic sulfonamide scaffold were achieved and this potency increase translated in an improved in vivo efficacy.
Ye, Xiaocong M.,Konradi, Andrei W.,Smith, Jenifer,Xu, Ying-Zi,Dressen, Darren,Garofalo, Albert W.,Marugg, Jennifer,Sham, Hing L.,Truong, Anh P.,Jagodzinski, Jacek,Pleiss, Michael,Zhang, Hongbin,Goldbach, Erich,Sauer, John-Michael,Brigham, Elizabeth,Bova, Michael,Basi, Guriqbal S.
scheme or table
p. 2195 - 2199
(2010/07/05)
Piperidinolysis of 4-Nitrophenyl X-Substituted benzenesulfonates and related compounds: Effect of changing leaving group and electrophilic center
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Um, Ik-Hwan,Akhtar, Kalsoom
experimental part
p. 234 - 237
(2010/08/06)
N-CYCLIC SULFONAMIDO INHIBITORS OF GAMMA SECRETASE
The invention provides N-cyclic sulfonamido compounds for use in treating or preventing cognitive disorders, such as Alzheimer’s Disease. Compounds of particular interest are defined by Formula (I), wherein R4, R5, R6, Rs
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Page/Page column 50
(2010/02/14)
Effect of Amine Nature on Reaction Rate and Mechanism in Nucleophilic Substitution Reactions of 2,4-Dinitrophenyl X-Substituted Benzenesulfonates with Alicyclic Secondary Amines
Second-order rate constants have been measured for reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with a series of alicyclic secondary amines. The reaction proceeds through S-O and C-O bond fission pathways competitively. The S-O bond fission occurs more dominantly as the amine basicity increases and the substituent X in the sulfonyl moiety becomes more strongly electron withdrawing, indicating that the regioselectivity is governed by the amine basicity as well as the electronic nature of the substituent X. The S-O bond fission proceeds through an addition intermediate with a change in the rate-determining step at pKa° = 9.1. The secondary amines are more reactive than primary amines of similar basicity for the S-O bond fission. The k1 value has been determined to be larger for reactions with secondary amines than with primary amines of similar basicity, which fully accounts for their higher reactivity. The second-order rate constants for the S-O bond fission result in linear Yukawa-Tsuno plots while those for the C-O bond fission exhibit poor correlation with the electronic nature of the substituent X. The distance effect and the nature of reaction mechanism have been suggested to be responsible for the poor correlation for the C-O bond fission pathway.
Arenesulfonylheterocycles (I): Synthesis and reactions of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with amines
The direct sulfonylation of 4,5-dichloropyridazin-3-ones with some benzenesulfonyl chlorides in the presence of base in tetrahydrofuran gave only the corresponding N-sulfonylated product. The reaction of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with some aliphatic amines under neutral conditions afforded 5-alkylamino-2-benzenesulfonyl-4-chloropyridazin-3-ones and/or the corresponding N-alkyl-benzenesulfonamides.
Kweon, Deok-Heon,Kim, Ho-Kyun,Kim, Jeum-Jong,Chung, Hyun A.,Woo, Song Lee,Kim, Sung-Kyu,Yoon, Yong-Jin
p. 203 - 211
(2007/10/03)
Nitrosations of hydrazine derivatives, XII: - Thermolysis of arenesulfonyltriazenes to arenesulfonamides
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Hanefeld,Hartmann
p. 837 - 838
(2007/10/02)
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