53440-57-6

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 5328, 1992 DOI: 10.1021/jo00046a012

Upstream product

• 54075-06-8 2-benzoyl-benzenesulfonyl chloride 
• 71-43-2 benzene 
• 18712-15-7 3-ethoxy-benzo[d]isothiazole 1,1-dioxide 
• 591-51-5 phenyllithium 
• 1709-51-9 N,N-diphenylbenzenesulfonamide 
• 100-47-0 benzonitrile 
• 81-07-2 saccharin 
• 7446-70-0 aluminium trichloride 
• 7664-41-7 ammonia 
• 57683-71-3 methyl 2-(aminosulfonyl)benzoate 
• 109-72-8 n-butyllithium 
• 136481-64-6 N-tert-butyl-2-(α-hydroxybenzyl)benzenesulphonamide 
• 7664-93-9 sulfuric acid 
• 2512-24-5 N-tert-butylbenzenesulfonamide 

Downstream Products

• 61798-57-0 (1,1-dioxo-4-methyl-5-phenyl-1H-1λ⁶-benzo[f]thiazepin-3-yl)-diethyl-amine 
• 124401-11-2 7b-phenyl-7bH-oxazirino<2,3-b><1,2>benzisothiazole 3,3-dioxide 
• 53983-81-6 2,3-Dihydro-3,3-diphenyl-1,2-benzisothiazole 1,1-dioxide 
• 61766-87-8 2-((Z)-3-Diethylamino-2-methyl-1-phenyl-propenyl)-benzenesulfonamide 
• 1269473-37-1 1,9b-diphenyl-1,2-dihydrobenzo[d]pyrrolo[1,2-b]isothiazol-3-one 5,5-dioxide 
• 1093168-66-1 rac-9b-phenyl-1,2-dihydrobenzo[d]pyrrolo[1,2-b]isothiazol-3-one 5,5-dioxide 

Relevant academic research and scientific papers

The Preparation of 3-Substituted 1,2-Benzisothiazole 1,1-Dioxides from Lithiated Intermediates or Grignard Reagents and Methyl 2-(Aminosulfonyl)benzoate

A polylithiated β-ketoester, β-diketone, or β-ketoamide was condensed-cyclized with lithiated methyl 2-(Aminosulfonyl)benzoate, to afford new 3-substituted 1,2-benzisothiazole 1,1-dioxides. Some Grignard or organolithium reagents were also condensed-cyclized with methyl 2-(aminosulfonyl)benzoate to give 3-substituted 1,2-benzisothiazole 1,1-dioxides.

Energy-, time-, and labor-saving synthesis of α-ketiminophosphonates: Machine-learning-assisted simultaneous multiparameter screening for electrochemical oxidation

A highly efficient synthesis of α-ketiminophosphonates has been established for the electrochemical oxidation of α-amino phosphonates with the utilization of machine-learning-assisted simultaneous multiparameter screening. After brief experimental screening, the Bayesian optimization with the experimental data (up to 12 entries) could rapidly predict the optimal conditions for the synthesis of α-ketiminophosphonates and sulfonyl ketimines with aryl and alkyl groups. The obtained α-ketiminophosphonates could be converted into highly functionalized α-amino acid analogues with a tetrasubstituted carbon center.

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Efficient visible-light photocatalytic aerobic oxidation of cyclic sulfamides to imines

A highly efficient photocatalytic aerobic oxidation of cyclic sulfamides to synthesize cyclic N-sulfonyl imines with Ir(ppy)2(dtbpy)PF6 as photocatalyst is reported. These environmentally friendly transformations exihibit good to excellent isolated yields and good generality with respect to both five-membered and six-membered cyclic sulfamides.

Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C?H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines

The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C?H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines. (Figure presented.).

B(C6F5)3-Catalyzed Reduction of Cyclic N-Sulfonyl Ketimines

A metal-free method for reduction of cyclic N-sulfonyl ketimines catalyzed by B(C6F5)3, using commercially available methylphenylsilane as a reducing reagent under mild conditions has been developed. This reductive protoco

Nickel-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Imines

An efficient nickel-catalyzed asymmetric hydrogenation of N-tBu-sulfonyl imines was developed with excellent yields and enantioselectivities using (R,R)-QuinoxP* as a chiral ligand. The use of a much lower catalyst loading (0.0095 mol %, S/C=10500) represents the highest catalytic activity for the Ni-catalyzed asymmetric hydrogenations reported so far. Mechanistic studies suggest that a coordination equilibrium exists between the nickel salt and its complex, and that excess nickel salt promotes the formation of the active Ni-complex, and therefore improved the efficiency of the hydrogenation. The catalytic cycle was also investigated by calculations to determine the origin of the enantioselectivity. An extensive network of numerous weak attractive interactions was found to exist between the catalyst and substrate in the transition state and may also contribute to the high catalytic activity.

Asymmetric transfer hydrogenation reactions of: N -sulfonylimines by using alcohols as hydrogen sources

A palladium/zinc co-catalytic system was established and successfully utilized in the asymmetric transfer hydrogenation reactions of N-sulfonylimines with alcohols as hydrogen sources. Simple alcohols such as methanol, ethanol and benzyl alcohols are all

Pd/Zn(OTf)2 Co-Catalyzed Asymmetric Hydrogenation of Imines under Normal Pressure of Hydrogen

An efficient method for the asymmetric hydrogenation of cyclic and acyclic N-sulfonylimines co-catalyzed by Pd/Zn(OTf)2 using hydrogen gas under ambient pressure was developed. The methodology offers an easy access to generate chiral sulfonylam

Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides

A general protocol for iridium catalyzed direct C?H amidation of cyclic N-sulfonyl ketimines using sulfonyl, acyl and aryl azides as nitrogen source is reported herein. The reaction takes place at room temperature with acyl and aryl azides, while an elevated temperature needed with sulfonyl azides to furnish aminated sultams in excellent yields with complete chemo and regioselectivity, thus providing a robust and environmentally benign process to the synthesis of aminosultams. (Figure presented.).