17196-74-6

Upstream product

• 3755-96-2 (2Z)-3-bromo-3-phenylprop-2-enenitrile 
• 60-29-7 diethyl ether 
• 100-47-0 benzonitrile 
• 75-05-8 acetonitrile 
• 614-16-4 Benzoylacetonitrile 
• 33440-88-9 silver phenylacetylide 
• 73789-56-7 N-isocyaniminotriphenylphosphorane 
• 536-74-3 phenylacetylene 
• 140-29-4 phenylacetonitrile 
• 99749-00-5 lithioacetonitrile 
• 14904-36-0 cis-trans-3--cinnamonitril 
• 14904-42-8 cis-trans-3-Trimethylsilylamino-cinnamonitril 

Downstream Products

• 21628-33-1 6-amino-3-cyano-2,4-diphenylpyridine 
• 7758-73-8 5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one 
• 4847-47-6 β-(phenylamino)-cinnamic acid nitrile 
• 861318-51-6 4-chloromethyl-2,6-diphenyl-1,4-dihydro-pyridine-3,5-dicarbonitrile 
• 100784-53-0 6-hydroxy-2,4-diphenyl-nicotinonitrile 
• 846549-50-6 5-cyano-2,6-diphenyl-nicotinic acid ethyl ester 
• 55249-89-3 3-cyano-2,4,6-triphenylpyridine 
• 13491-70-8 phenylhydrazonobenzoylacetonitrile 
• 42412-19-1 3-phenyl-3-phenylhydrazono-propionitrile 
• 4369-55-5 3-phenyl-isoxazol-5-ylamine 
• 52028-95-2 β-amino-cinnamic acid amide 

Relevant academic research and scientific papers

Cu-catalyzed ring opening reaction of 2H-azirines with terminal alkynes: An easy access to 3-alkynylated pyrroles

A highly efficient Cu-catalyzed ring expansion reaction of 2H-azirines with terminal alkynes has been developed. This transformation provides a powerful method for the synthesis of 3-alkynyl polysubstituted pyrroles under mild conditions in good yields. The direct transformation process, specific selectivity, and good tolerance to a variety of substituents make it an alternative approach to the reported protocols.

Tandem Thorpe Reaction/Palladium Catalyzed Asymmetric Allylic Alkylation: Access to Chiral β-enaminonitriles with Excellent Enantioselectivity

A new type of nucleophile, a 3-imino nitrile carbanion generated in situ by Thorpe reaction of acetonitrile with a base, was developed successfully and applied in a Pd-catalyzed asymmetric allylic alkylation with mono-substituted allyl reagents under Pd/S

Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines

A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp2)-H functionalization of alkenes, offering 26 enynes in 62-92% yield with excellent functional group tolerance.

Green synthesis method of nicotinic acid ester compounds based on non-metallic conditions

The invention discloses a green synthesis method based on nicotinic acid ester compounds under non-metallic conditions, and belongs to the technical field of organic synthesis. The method comprises the following steps of (III) replacing cyclopropanol and (II) substituted enamine ester as a raw material, taking tetramethyl piperidine nitrogen oxide as an oxidizing agent, 110 - 130 °C, stirring and reacting in an organic solvent to synthesize a (I) nicotinate compound. The invention provides a green synthesis method based on nicotinic acid ester compounds under non-metallic conditions, wherein cyclopropanols and enamine esters are taken as raw materials, and a polysubstituted nicotinate is synthesized through a strategy of oxidative dehydrogenation of ketene cyclization.

Cobaloxime Catalysis for Enamine Phosphorylation with Hydrogen Evolution

Direct phosphorylation of enamine and enamide with hydrogen evolution was realized via cobaloxime catalysis under visible-light irradiation. Control experiments and spectroscopic studies demonstrated a reductive quenching pathway of cobaloxime catalyst to produce phosphinoyl radical, which underwent cross-coupling with various enamines (and enamides) to give diverse β-phosphinoyl products in good to excellent yields. More interestingly, Z/E mixture of acyclic enamines could convert into single Z-products with good reactivity.

Silver-promoted regio- and stereoselective aminocyanation of alkynes for the synthesis of β-aminoacrylonitriles using N-isocyanoiminotriphenylphosphorane

The silver-promoted intermolecular aminocyanation of alkynes for the synthesis of (Z)-β-aminoacrylonitriles is reported, using N-isocyanoiminotriphenylphosphorane (NIITP) as both the nitrile and amine source. The transformation proceeds in moderate to good yields, and in a regio- and stereoselective manner, using a wide range of acetylenes.

Multi-component synthesis of 3-substituted indoles and their cyclisation to α-carbolines: Via I2-promoted intramolecular C2 oxidative amination/aromatisation at room temperature

Condensation of indoles, aldehydes and pyrazol-5-amine in the presence of ceric ammonium nitrate gives 3-substituted indoles. These then cyclise to α-carbolines at room temperature through I2-promoted intramolecular C2 amination and aromatisation in open air. A plausible mechanism is proposed based on some controlled experiments.

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.

In situ click chemistry generation of cyclooxygenase-2 inhibitors

Cyclooxygenase-2 isozyme is a promising anti-inflammatory drug target, and overexpression of this enzyme is also associated with several cancers and neurodegenerative diseases. The amino-acid sequence and structural similarity between inducible cyclooxygenase-2 and housekeeping cyclooxygenase-1 isoforms present a significant challenge to design selective cyclooxygenase-2 inhibitors. Herein, we describe the use of the cyclooxygenase-2 active site as a reaction vessel for the in situ generation of its own highly specific inhibitors. Multi-component competitive-binding studies confirmed that the cyclooxygenase-2 isozyme can judiciously select most appropriate chemical building blocks from a pool of chemicals to build its own highly potent inhibitor. Herein, with the use of kinetic target-guided synthesis, also termed as in situ click chemistry, we describe the discovery of two highly potent and selective cyclooxygenase-2 isozyme inhibitors. The in vivo anti-inflammatory activity of these two novel small molecules is significantly higher than that of widely used selective cyclooxygenase-2 inhibitors.

Acid-promoted rapid solvent-free access to substituted 1,4-dihydropyridines from β-ketothioamides

β-Ketothioamides (KTAs) have been used as building blocks with aldehydes and β-enaminonitriles for synthesis of 1,4-dihydropyridines in the presence of AcOH under solvent-free conditions within 5 min. This new strategy exhibits remarkable features such as high chemoselectivity, mild reaction conditions, easily available substrates, and good yields.