155059-95-3

Upstream product

• 123-75-1 pyrrolidine 
• 994-89-8 tributylethynyltin 
• 100-52-7 benzaldehyde 
• 75-20-7 calcium carbide 
• 1066-54-2 trimethylsilylacetylene 
• 14630-40-1 Bis(trimethylsilyl)ethyne 

Downstream Products

• 1146542-86-0 C₂₆H₂₈N₂ 
• 615253-71-9 1-(1,3-diphenylprop-2-yn-1-yl)pyrrolidine 

Relevant academic research and scientific papers

Altering Copper-Catalyzed A3 Couplings by Mechanochemistry: One-Pot Synthesis of 1,4-Diamino-2-butynes from Aldehydes, Amines, and Calcium Carbide

The ability of mechanochemistry to alter established chemical selectivity is demonstrated. A copper(I)-catalyzed mechanochemical aldehyde/alkyne/amine coupling using calcium carbide as the acetylene source provides selective access to 1,4-diamino-2-butynes, which contrasts classical approaches that provide propargylamine-type products. Solventless milling conditions were found to be essential to unmask A3 coupling products with new compositions.

Ag2CO3-catalyzed efficient synthesis of internal or terminal propargylicamines and chalcones via A3-coupling under solvent-free condition

Several simple, fast and practical protocols have been developed to synthesize internal or terminal propargylamines and chalcones via A3-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag2CO3 under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated. Furthermore, plausible mechanisms for the synthesis of different products have been proposed.

Synthesis of propargylamines: Via the A3 multicomponent reaction and their biological evaluation as potential anticancer agents

Propargylamines have gained importance in the area of anticancer research. We synthesized 1-substituted propargylic tertiary amines using the A3-coupling as the key step. Both, solution and solid-phase protocols, were used to provide a library of 1-substituted propargylic tertiary amines with interesting structural diversity. The triple negative breast cancer subtype is the most aggressive and it lacks effective therapeutic options, while pancreatic cancer is one of the neoplasms with worse prognosis and limited therapeutic possibilities. The development of tumor-selective drugs has always been a major challenge in cancer treatment. From our library, two propargylamines displayed a high degree of cytotoxic selectivity. These levels of selectivity give a very interesting perspective for further development of 1-substituted propargylic tertiary amines as new potential chemotherapeutic antitumor agents.

Phase-Vanishing Method with Acetylene Evolution and Its Utilization in Several Organic Syntheses

A novel quadraphasic phase-vanishing system in which acetylene is evolved from calcium carbide and directly applied in situ to the Sonogashira coupling reaction was developed. This method, which provides a safe, convenient, and one-pot means to utilize gaseous reagents without special equipment, was also applied to a Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and a three-component aldehyde-alkyne-amine (A3) coupling reaction with excellent results. (Figure Presented).

PROCESS FOR PRODUCING AN AMINOPROPYNE OR ENAMINONE

There is provided a process for producing an aminopropyne or an enaminone comprising the step of reacting a metal acetylide, an amine and a carbonyl-containing compound in the presence of a transition metal catalyst. There is also provided a process for producing an aminopropyne comprising the step of reacting a metal acetylide, an amine and a halide-containing compound in the presence of a transition metal catalyst at a reaction temperature of 50°C to 150°C. There are also provided processes to further synthesize the aminopropyne produced to obtain a butyneamine, another aminopropyne or a triazol.

Acetylide Ion (C22-) as a synthon to link electrophiles and nucleophiles: A simple method for enaminone synthesis

Friendly competition: A three-component reaction system composed of calcium carbide, an aryl aldehyde, and an amine gave enaminones or propargylamines (see picture) in a predictable manner through competitive pathways. The system enables the cost-efficient synthesis of a variety of enaminones from readily accessible small molecules and demonstrates the versatility of the acetylide ion, which can be used to bridge electrophiles and nucleophiles. Copyright

Synthesis of functional acetylene derivatives from calcium carbide

AHA Erlebnis: CaC2, used to produce acetylene until several decades ago, is re-emerging as a cheap, sustainable resource synthesized from coal and lignocellulosic biomass. We report efficient catalytic protocols for the synthesis of functional acetylene derivatives from CaC2 through aldehyde, alkyne, and amine (AAA) as well as alkyne, haloalkane, and amine (AHA) couplings, and in addition demonstrate its use in click and Sonogashira chemistry, showing that calcium carbide is a sustainable and cost-efficient carbon source.

Copper(I) halide catalyzed three-component coupling reaction of aldehyde, pyrrolidine and stannyl- and silylacetylene

An efficient three-component coupling reaction of aldehyde, pyrrolidine and tributylstannylacetylene or triphenylsilylacety-lene to generate propargylamines has been developed by using copper(I) halides as promoters. Georg Thieme Verlag Stuttgart.

Copper(I)-Catalyzed Amination of Propargyl Esters. Selective Synthesis of Propargylamines, 1-Alken-3-ylamines, and (Z)-Allylamines

Copper(I)-catalyzed aminations of propargyl phosphates and acetates proceed under mild reaction conditions to give the corresponding propargylamines which are precursors of 1-alken-3-ylamines and (Z)-allylamines.