76883-63-1

Upstream product

• 99-03-6 1-(3-aminophenyl)ethanone 
• 98-09-9 benzenesulfonyl chloride 
• 95-14-7 1,2,3-Benzotriazole 
• 4106-18-7 1-(phenylsulfonyl)-1H-benzo[d][1,2,3]triazole 
• 121-89-1 3-Nitroacetophenone 

Downstream Products

• 137690-31-4 N-{3-[3-(2-hydroxy-phenyl)-acryloyl]-phenyl}-benzenesulfonamide 
• 137690-42-7 N-{3-[3-(3-chloro-phenyl)-acryloyl]-phenyl}-benzenesulfonamide 
• 137690-32-5 N-{3-[3-(3-hydroxy-phenyl)-acryloyl]-phenyl}-benzenesulfonamide 
• 137690-29-0 N-{3-[3-(3-methoxy-phenyl)-acryloyl]-phenyl}-benzenesulfonamide 
• 137690-36-9 N-{3-[3-(2-nitro-phenyl)-acryloyl]-phenyl}-benzenesulfonamide 
• 137690-39-2 N-{3-[3-(4-amino-phenyl)-acryloyl]-phenyl}-benzenesulfonamide 
• 844679-46-5 N-(3-acetylphenyl)-N-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor

Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.

Solvent hydrogen bonding and structural effects on nucleophilic aromatic substitution reactions. Part-2: Reaction of benzenesulphonyl chloride with anilines in propan-2-ol/2-methylpropan-2-ol mixtures

Substitution reactions of fourteen para- and meta-substituted anilines with benzenesulphonyl chloride in different mole fractions of propan-2-ol in 2-methylpropan-2-ol have been investigated conductometrically. The second order rate constants correlates satisfactorily with pKa values of the anilines and also with the Hammett's substituent constant. The para-substituted anilines shows a satisfactory correlation with Charton's LDR equation. The results of these correlations indicate the formation of an electron deficient transition state. The rate data correlate satisfactorily with macroscopic solvent parameters such as relative permittivity, εr and polarity, ETN. Multiple correlation analysis of the rate data via Kamlet-Taft's solvatochromic parameters reveals that the solvent dipolarityfpolarizability plays a dominant role in governing the reactivity.

Solvent hydrogen bonding and structural effects on nucleophilic substitution reactions: Part 3. Reaction of benzenesulfonyl chloride with anilines in benzene/ propan-2-ol mixtures

Substitution reactions of 13 para- and meta-substituted anilines with benzene-sulfonyl chloride in varying mole fractions of benzene in propan-2-ol have been investigated conductometrically, The second-order rate constants correlate well with pKa values of anilines and with the Hammett's equation. The negative Hammett reaction constant indicates the formation of an electron-deficient transition state. The rate data correlate satisfactorily with macroscopic solvent parameters such as relative permittivity, εr, and polarity, ETN. Correlation of rate data with Kamlet-Taft solvatochromic parameters (α, β, π*) suggests that both the specific and nonspecific solute-solvent interactions influence the reactivity.

Solvent hydrogen bonding and structural effects on nucleophilic substitution reactions. Part-1: Reaction of benzenesulphonyl chloride with anilines in benzene/2-methylpropan-2-ol-mixtures

Substitution reactions of eleven para- and meta-substitutcd anilines with benzencsulphonyl chloride in different mole fractions of benzene in 2-methylpropan-2-ol have been investigated conductometrically. The second order rate constants don't correlate either with pK values of the anilines or with the Hammett's and its modified equations. The para-substituted anilines shows a satisfactory correlation with Charton's LDR equation and the results indicate the formation of an electron deficient transition state. The rate data correlate satisfactorily with macroscopic solvent parameters such as relative permittivity, εr, and polarity, ETN. Multiple correlation analysis of the rate data via Kamlet-Taft's solvatochromic parameters reveals that the solvent hydrogen bond donor property plays a dominant role in governing the reactivity.

Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase

α,γ-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the γ position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.