609769-63-3

Usage

Uses

Used in Chemical Synthesis:
N-benzyl-N-(p-toluenesulfonyl)-2-phenylethynylamine is used as a building block for the design and synthesis of a wide range of chemical transformations. Its strong polarization and reactivity make it a valuable component in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
N-benzyl-N-(p-toluenesulfonyl)-2-phenylethynylamine is used as a precursor for the generation of highly reactive keteniminium ions. These ions are crucial intermediates in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, N-benzyl-N-(p-toluenesulfonyl)-2-phenylethynylamine serves as a useful reagent. Its unique structure and reactivity enable the selective formation of chiral molecules with specific stereochemistry, which is essential for the development of enantiomerically pure drugs and other biologically active compounds.
Used in Material Science:
N-benzyl-N-(p-toluenesulfonyl)-2-phenylethynylamine can also be employed in the development of novel materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with tailored characteristics, such as improved conductivity, mechanical strength, or optical properties.

Upstream product

• 591-50-4 iodobenzene 
• 205885-39-8 N-benzyl-N-ethynyl-4-methyl-benzenesulfonamide 
• 7436-90-0 2,2-dibromostyrene 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 100-46-9 benzylamine 
• 6607-46-1 (1,2-dibromovinyl)benzene 
• 536-74-3 phenylacetylene 
• 1483-82-5 phenylethynyl chloride 
• 58723-96-9 (Z)-1,2-dichloro-2-phenylethylene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 312329-82-1 N-(2,2-dichlorovinyl)-N-benzyl-4-methyl-benzenesulfonamide 
• 312329-77-4 N-benzyl-N-formyl-4-methyl-benzenesulfonamide 

Downstream Products

• 97306-02-0 N-benzyl-N-(2,2-diphenylethenyl)toluene-p-sulphonamide 
• 1187370-53-1 (E)-N-benzyl-N'-(2-iodophenyl)-2-phenyl-N-tosylacetimidamide 
• 1258303-42-2 C₂₂H₂₁NO₂S 
• 1092383-18-0 N-benzyl-2-oxo-2-phenyl-N-p-toluenesulfonylacetamide 
• 1351220-30-8 (R)-ethyl 4-(N-benzyl-4-methylphenylsulfonamido)-3-phenyl-2-(trifluoromethyl)-2H-oxete-2-carboxylate 
• 1351220-33-1 diethyl 2-(2-(N-benzyl-4-methylphenylsulfonamido)-2-oxo-1-phenylethylidene)malonate 
• 1356545-27-1 3,5-dimethoxybenzoic acid (E)-1-[benzyl-(toluene-4-sulfonyl)amino]-2-phenylvinyl ester 
• 1375415-34-1 (E)-N-benzyl-N-(1-fluoro-2-phenylvinyl)-4-methylbenzenesulfonamide 
• 534591-08-7 (R,E)-3-(1-iodo-2-phenylvinyl)-4-phenyloxazolidin-2-one 
• 1422721-66-1 (E)-N-benzyl-N-(1-iodo-2-phenylvinyl)-4-methylbenzenesulfonamide 
• 1433278-68-2 N-benzyl-3-(1,3-dithian-2-ylidene)-2-phenyl-N-tosylpropanamide 
• 1629962-32-8 (E)-N-benzyl-N-(1-bromo-2-iodo-2-phenylvinyl)-4-methylbenzenesulfonamide 
• 1617518-96-3 (Z)-N-benzyl-N-[2-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-4-methylbenzenesulfonamide 
• 1645293-05-5 C₂₈H₁₉N₅O₂S 

Relevant academic research and scientific papers

Synthesis of Sulfonamide-Based Ynamides and Ynamines in Water

Ynamides, though relatively more stable than ynamines, are still moisture-sensitive and prone to hydration especially under acidic and heating conditions. Here we report an environmentally benign, robust protocol to synthesize sulfonamide-based ynamides and arylynamines via Sonogashira coupling reactions in water, using a readily available quaternary ammonium salt as the surfactant.

Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis

Arene dearomatization is a straightforward method for converting an aromatic feedstock into functionalized carbocycles. Enantioselective dearomatizations of chemically inert arenes, however, are quite limited and underexplored relative to those of phenols and indoles. We developed a method for diazo-free generation of silver-carbene species from an ynamide and applied it to the dearomatization of nonactivated arenes. Transiently generated norcaradiene could be trapped by intermolecular [4 + 2] cycloaddition, synthesizing polycycles with five consecutive stereogenic centers. This protocol constitutes the first highly enantioselective reaction based on the diazo-free generation of silver-carbene species. Mechanistic investigations revealed a dearomatization followed by two different classes of pericyclic reactions, as well as the origin of the chemo- and enantioselectivity.

Direct oxidation ofN-ynylsulfonamides intoN-sulfonyloxoacetamides with DMSO as a nucleophilic oxidant

N-Arylethynylsulfonamides are oxidized intoN-sulfonyl-2-aryloxoacetamides directly and efficiently with dimethyl sulfoxide (DMSO) as both an oxidant and solvent with microwave assistance. DFT calculations indicate that DMSO nucleophilically attacks the ethylic triple bond and transfers its oxygen atom to the triple bond to form zwitterionic anionicN-sulfonyliminiums to trigger the reaction. Then it nucleophilically attacks the generated iminium intermediates to accomplish the oxidationviathe second oxygen atom transfer. The current method provides a straightforward and efficient strategy to transform variousN-arylethynylsulfonamides intoN-sulfonyl-2-aryloxoacetamides, sulfonyl oxoacetimides, without any other electrophilic activators or oxidants.

Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: Highly regioselective synthesis of 2,4,6-triaminopyrimidines

Triflic acid (10 mol%) catalyzes the highly regioselective [2 + 2 + 2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed density functional theory calculations verified a particular role of H+, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition.

Nickel-catalyzed regioselective hydroamination of ynamides with secondary amines

The first Ni(OTf)2-catalyzed hydroamination of ynamides 2 was developed by reacting with secondary amines (1 and 4). This protocol features excellent regioselectivity, a broad substrate scope of secondary aryl amines, and good functional group tolerance for ynamides. Using this method, a variety of substituted ethene-1,1- diamine compounds were prepared in moderate to excellent yields with high regioselectivities.

Metal-Free Hydrophosphoryloxylation of Ynamides: Rapid Access to Enol Phosphates

We herein report a metal-free hydrophosphoryloxylation of ynamides with phosphoric acids, which provides an expeditious route to access useful enol phosphates. The advantages of this protocol include exclusive selectivity, short reaction time, high efficiency, and broad substrate scope. Additionally, the products can serve as good partners in Suzuki-Miyaura cross-coupling.

TMSOTf-mediated approach to 1,3-oxazin-2-one skeleton through one-pot successive reduction-[4 + 2] cyclization process of imides with ynamides

A one-pot approach to access functionalized 1,3-oxazin-2-one skeleton has been developed through successive reduction and subsequent [4 + 2] cyclization process of N-Boc lactams with ynamides by TMSOTf. As a result, a number of five to seven membered ring fused bicyclic [1,2-c][1,3]oxazin-1-ones 12a-m and tricyclic derivatives 13a-f were obtained in moderate to excellent yields with excellent regioselectivities. Moreover, linear N-Boc amides 9a-e were also amenable to this transformation, and the desired 3,4-dihydro-1,3-oxazin-2-ones 14a-m were readily achieved in moderate yields with excellent regioselectivities.

Synthesis of dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline through Cu(OTf)2-catalyzed reactions of N-acyliminium ions with ynamides

An efficient approach to access functionalized dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline skeletons has been developed through the addition-cyclization process of ynamides 8 with N-acyliminium ions generated from N,O-acetals 6,7. The reactions were conducted under the catalysis of Cu(OTf)2, and a number of functionalized dihydro-[1,3]oxazino[4,3-a] isoindoles 9a-9y and tetrahydroisoquinolines 10a-10g, 11a-11p were generated in 48–98% yields. When chiral ynamides 8n-8u were used, optically pure products 11a-11p could be obtained with good to excellent yields and diastereoselectivities.

Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)2-Catalyzed Reactions of Ynamides with t-Butyl Carbamates/Carbonates

A highly regioselective approach to access amide enol carbamates and carbonates 5a-5c′, 7a-7h, and 9 was developed through Cu(OTf)2-catalyzed reactions of ynamides 4 with t-butyl carbamates 2 and 8 and t-butyl carbonates 6. Moreover, this strategy was successfully applied to generate amide enol carbamates 11a-11s and 14a-14f from imides 10 and 13 with ynamides through an N-Boc cleavage-addition ring-opening process. A range of substituents was amenable to this transformation, and the desired amide enol carbamates and carbonates were obtained in moderate to good yields.

Synthesis of a 3,4-Dihydro-1,3-oxazin-2-ones Skeleton via an Intermolecular [4 + 2] Process of N-Acyliminium Ions with Ynamides/Terminal Alkynes

An approach to access functionalized 3,4-dihydro-1,3-oxazin-2-ones has been developed by reacting semicyclic N,O-acetals 5 and 6 with ynamides 7 or terminal alkynes 8 in a one-pot fashion. The reaction went through a formal [4 + 2] cycloaddition process to generate a number of functionalized 3,4-dihydro-1,3-oxazin-2-ones 9a-9ak and 10a-10bc in yields of 34-97%. In addition, the utility of this transformation was demonstrated by the synthesis of (±)-sedamine 13.