683246-83-5

Upstream product

• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 111409-79-1 1-bromo-2-(triisopropylsilyl)acetylene 
• 160481-43-6 (iodoethynyl)triisopropylsilane 
• 89343-06-6 tris-iso-propylsilyl acetylene 
• 100-46-9 benzylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 205885-39-8 N-benzyl-N-ethynyl-4-methyl-benzenesulfonamide 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 

Relevant academic research and scientific papers

Regioselective iodoamination of terminal ynamides for the synthesis of α-amino-β,β-diiodo-enamides

A mild and efficient methodology involving the I2/TBHP-mediated intermolecular iodoamination of ynamides with amines for the synthesis of α-amino-β,β-diiodo-enamides was developed. This reaction provides the first intermolecular iodoamination o

Copper-Catalyzed Synthesis of Terminal vs. Fluorine-Substituted N-Allenamides via Addition of Diazo Compounds to Terminal Ynamides

A copper-mediated coupling reaction between ynamides and diazo-compounds to produce N-allenamides is reported for the first time. This method enables facile and rapid access to terminal N-allenamides by using commercially available TMS-diazomethane with w

Metal-free C8-H functionalization of quinolineN-oxides with ynamides

The metal-free C8-H functionalization of quinolineN-oxides with ynamides is unveiled for the first time by the intramolecular Friedel-Crafts-type reaction of quinolyl enolonium intermediates generated from Br?nsted acid-catalyzed addition of quinolineN-ox

Direct Synthesis of CF2H-Substituted 2-Amidofurans via Copper-Catalyzed Addition of Difluorinated Diazoacetone to Ynamides

The significance of molecules containing difluoromethyl groups is driven by their potential applications in pharmaceutical and agrochemical science. Methods for the incorporation of lightly fluorinated groups such as CF2H have been less well developed. He

Gold-Catalyzed Oxidations of 1,3-Diynamides with C(1) versus C(3) Regioselectivity: Catalyst-Dependent Oxidative Cyclizations in the C(3) Oxidation

This work reports two distinct paths in catalytic oxidations of 1,3-diynamides with 8-methylquinoline oxide. A typical C(1) regioselectivity was observed for aryl-substituted 1,3-diyn-1-amides, whereas an unexpected C(3) regioselectivty occurred for 5-hydroxy1,3-diyn-1-amides. We focused on the C(3) oxidations of 5-hydroxy1,3-diyn-1-amides because we observed two oxidative cyclizations of the same substrates to yield 2-aminomethylenefuran-3(2H)-ones and 2-amino-4H-pyran-4-ones using AuCl3 and a cationic gold catalyst, respectively. Density functional theory calculations were performed to rationalize the C(3) regioselectivity on 5-hydroxy1,3-diyn-1-amides.

A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water

Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.

Highly Selective Syn Addition of 1,3-Diones to Internal Ynamides Catalyzed by Zinc Iodide

1,3-Diones are already established as nucleophiles to perform additions to ynamides; the highly selective hydroalkoxylation of internal ynamides is now described. Several catalytic systems have been compared to perform this transformation, including transition-metal-based catalysts and Lewis acids. ZnI2 was found to be both very active and highly selective providing only E adducts through a syn addition. Investigation of the scope and limitations showed that this catalyst was compatible with various functional groups. In addition to seventeen examples of ynamide hydroalkoxylation, one example of ynamide hydroarylation is reported.

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.

Tf2NH-catalyzed formal [3 + 2] cycloaddition of oxadiazolones with ynamides: a simple access to aminoimidazoles

Oxadiazolones are first employed as the three-atom coupling partners in the Tf2NH-catalyzed cycloaddition with ynamides. This formal [3 + 2] cycloaddition allows a rapid synthesis of aminoimidazoles with a broad substrate scope. The approach also features a metal-free catalytic cycloaddition process, which may find applications in the synthesis of bioactive molecules. Besides, the resulting N-methyl products can further be readily converted to free N-H aminoimidazoles.

Synthesis of Highly Functionalized 4-Aminoquinolines

A diverse set of highly substituted 4-aminoquinolines was synthesized from ynamides, triflic anhydride, 2-chloropyridine, and readily accessible amides in a mild one-step procedure. Diverse products: Electrophilically activated amides easily react with sulfonyl ynamides to yield a diverse range of substituted 4-aminoquinolines. The ynamides can be easily modified by Sonogashira processes or generated from dichloroenamide precursors. Any substituent can thus be introduced at the C3 position of the quinoline. 2-ClPy=2-chloropyridine, Tf2O=triflic anhydride.