127808-49-5

Upstream product

• 536-74-3 phenylacetylene 
• 14267-92-6 1-chloro-4-pentyne 
• 4440-01-1 lithium phenylacetylide 
• 24463-87-4 (5-chloropent-1-ynyl)benzene 
• 725736-60-7 5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid 5-phenyl-pent-4-ynyl ester 
• 154188-75-7 2-(5-phenylpent-4-yn-1-yl)isoindoline-1,3-dione 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 5003-71-4 3-bromopropylamine hydrochloride 

Downstream Products

• 53031-80-4 (E)-3-phenylmethylene-2-piperidinone 
• 141807-68-3 C₁₁H₁₁⁽²⁾H₂N 
• 258881-90-2 C₁₁H₁₃N 
• 1233536-62-3 C₁₄H₁₇N₃O₂ 

Relevant academic research and scientific papers

A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions

The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.

Facile one-pot synthesis of 2,3-dihydro-1H-indolizinium derivatives by rhodium(iii)-catalyzed intramolecular oxidative annulation via C-H activation: application to ficuseptine synthesis

Various substituted indolizidinium, quinolizinium and pyrido[1,2-a]azepinium salts synthesized from benzaldehydes (or α,β-unsaturated aldehydes) and alkyne-amines catalyzed by rhodium complexes via C-H activation are demonstrated. The reaction was carried

The acid-mediated intramolecular 1,3-dipolar cycloaddition of derived 2-nitro-1,1-ethenediamines for the synthesis of novel fused bicyclic isoxazoles

The discovery of a novel synthesis of new fused bicyclic isoxazoles, for example, N-methyl-3-phenyl-5,6-dihydro-4H-isoxazolo[3,4-c]azepin-8-amine (2a), N-methyl-3-phenyl-4,5-dihydroisoxazolo[3,4-c]pyridin-7-amine (2b) and N-methyl-3-phenyl-4H-pyrrolo[3,4-

Et2Zn-catalyzed intramolecular hydroamination of alkynyl sulfonamides and the related tandem cyclization/addition reaction

(Chemical Equation Presented) Intramolecular hydroamination of alkynyl amides was effected by a catalytic amount of Et2Zn (20 mol %) to form indole derivatives, and a tandem cyclization/nucleophilic addition procedure involving reaction of the indole zinc salt intermediate with acid chlorides or halides was developed to provide an efficient approach to C3-substituted indole derivatives when an excess of Et2Zn (120 mol %) was used.

Synthesis of a bioprobe for elucidation of target molecule of spongean anti-malarial peroxides

The reactants of an anti-malarial peroxide having a 6-carbomethoxymethyl-3- methoxy-1,2-dioxane moiety treated with FeSO4 were analyzed. For mechanistic study of the anti-malarial peroxide, two biotinylated probes to elucidate the target molecu

Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoalkynes

This contribution reports the efficient and regiospecific Cp'2LnCH(SiMe3)2 (Ln = La, Nd, Sm, Lu; Cp' = η5-Me5C5)- and Me2SiCp''2LnCH(SiMe3)2 (Ln = Nd, Sm; Cp'' = η5-Me4C5)-catalyzed hydroamination/cyclization of aliphatic and aromatic aminoalkynes of the formula RC≡C(CH2)(n)NH2 to yield the corresponding cyclic imines RCH2C=N(CH2)(n-1)CH2, where R, n, N(t) h-1 (°C) = Ph, 3, 77 (21°C); Ph, 3, 2830 (60°C); Me, 3, 96 (21°C); CH2=CMeCH2, 3, 20 (21°C); H, 3, 580 (21°C); Ph, 4, 4 (21°C); Ph, 4, 328 (60°C); Ph, 5, 0.11 (60°C); and SiMe3, 3, >7600 (21°C), and of aliphatic secondary amino-alkynes of the formula RC≡C(CH2)3NHR1 to generate the corresponding cyclic enamines RCH=CNR1(CH2)2CH2 where R, R1, N(t) h-1 (°C) = SiMe3, CH2=CHCH2, 56 (21°C); H, CH2=CHCH2, 27 (21°C); SiMe3, CH2=CH(CH2)3, 129 (21°C); and H, CH2=CH(CH2)3, 47 (21°C). Kinetic and mechanistic evidence is presented arguing that the turnover-limiting step is an intramolecular alkyne insertion into the Ln-N bond followed by rapid protonolysis of the resulting Ln-C bond. The use of larger metal ionic radius Cp'2LnCH(SiMe3)2 and more open Me2SiCp''2LnCH(SiMe3)2 complexes as the precatalysts results in a decrease in the rate of hydroamination/cyclization, arguing that the steric demands in the -C≡C- insertive transition state are relaxed compared to those of the analogous aminoolefin hydroamination/cyclization.

Synthesis of substituted α-methylene lactams by rhodium catalysed carbonylation of acetylenic amines

Reactions of γ- and β-aminoalkynes, (2) and (5) with hydrogen and carbon monoxide in the presence of rhodium catalysts give substituted α-methylene-2-piperidinones (7) and 2-pyrrolidinones (11).