683246-91-5

Upstream product

• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 7436-90-0 2,2-dibromostyrene 
• 536-74-3 phenylacetylene 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 5558-62-3 2-ethyl-2-phenyl-4-pentenenitrile 
• 5558-71-4 2,2-diphenyl-pent-4-enenitrile 
• 1005500-91-3 (E)-2-phenyl-1-[(2-propenyl)(p-tolylsulfonyl)amino]ethenyl diphenyldithiophosphinate 
• 1026133-73-2 N-[(Z)-2-phenyl-1-hexenyl]-N-2-propenyl-p-toluenesulfonamide 
• 1026133-74-3 N-[(Z)-1-deuterio-2-phenyl-1-hexenyl]-N-2-propenyl-p-toluenesulfonamide 
• 1026133-69-6 N-[(E)-2-phenyl-2-(trimethylsilyl)ethenyl]-N-2-propenyl-p-toluenesulfonamide 
• 1219156-12-3 C₁₈H₁₇NO₂S 
• 1259403-81-0 C₁₉H₂₁NO₃S 
• 1259403-82-1 C₂₀H₂₃NO₃S 
• 1259403-83-2 C₂₁H₂₅NO₃S 
• 1309861-81-1 C₂₄H₃₀N₂O₂S 
• 847740-67-4 N¹-benzyl-N²-(4-methylbenzenesulfonyl)-2-phenylacetamidine 
• 1375415-51-2 (E)-N-allyl-N-(1-fluoro-2-phenylvinyl)-4-methylbenzenesulfonamide 
• 1379536-53-4 N-allyl-N-(5-butyl-1-phenylpyrazolo[5,1-a]isoquinolin-2-yl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes

The gold-catalyzed reaction between benzofuroxans, functioning as nitrene transfer reagents, and N-allylynamides leads to 3-azabicyclo[3.1.0]hexan-2-imines. This highly selective annulation proceeds smoothly under mild conditions (5 mol % Ph3PAuNTf2, PhCl, 60 °C) and exhibits high functional group tolerance (21 examples, ≤96% yields). The obtained cyclopropanated products represent a useful synthetic platform with an easily modulated substitution pattern as illustrated by their postmodifications. Intramolecular cyclopropanation of gold α-imino carbene intermediates is suggested as a key step of the catalytic cycle.

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.

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.

Copper(I)-Catalyzed Enyne Oxidation/Cyclopropanation: Divergent and Enantioselective Synthesis of Cyclopropanes

An efficient copper(I)-catalyzed enyne oxidation/cyclopropanation for the modular synthesis of cyclopropane derivatives is described, which represents the first non-noble metal-catalyzed enynes oxidation/cyclopropanation by the in situ generated α-oxo copper carbenes. This protocol allows the assembly of valuable cyclopropane-γ-lactams in generally good to excellent yields with excellent diastereoselectivity. More significantly, the enantioselective version of enyne oxidation/cyclopropanation has been disclosed with chiral copper catalysts.

Stereoselective construction of fused cyclopropane from ynamide and its application to synthesis of small drug candidate molecules

Herein, we report the development of an asymmetric intramolecular cyclopropanation reaction under silver catalysis. The strategy is based on diazo-free silver–carbene generation, providing γ-lactam fused cyclopropane in an enantioenriched form. The ring s

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.

Stereoselective Synthesis of Pyrido- and Pyrrolo[1,2-c][1,3]oxazin-1-ones via a Nucleophilic Addition-Cyclization Process of N,O-Acetal with Ynamides

An efficient asymmetric approach to access functionalized pyrido- and pyrrolo[1,2-c][1,3]oxazin-1-ones has been developed through a nucleophilic addition-cyclization process of N,O-acetal with ynamides. A number of substituted ynamides 8a-8o and 3-silyloxypyrrolidine or piperidine N,O-acetals 6a, 7 were amenable to this transformation, and the desired products 9a-9o, 10a-10m were obtained with excellent regioselectivities and outstanding diastereoselectivities. Moreover, chiral ynamides 14a-14f could also experience this addition-cyclization process to afford products 15a-15f in excellent yields.

Gold(III)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines

We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the gram scale, tolerates electron-rich and electron-deficient anthranils as well as a diverse set of functionalized ynamides (aryl- and alkyl-substituted terminal).

Tf2NH-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with Dioxazoles: A Metal-Free Approach to Polysubstituted 4-Aminooxazoles

An unprecedented Tf2NH-catalyzed formal [3 + 2] cycloaddition of ynamides with dioxazoles was developed to construct various polysubstituted 4-aminooxazoles. This approach features a metal-free catalytic bimolecular assembly of oxazole motifs, a low-cost catalyst, exceptionally mild reaction conditions, a very short reaction time, a broad substrate scope, and high efficiency. This metal-free protocol may find applications in pharmaceutical-oriented synthesis.