100191-80-8

Upstream product

• 62-53-3 aniline 
• 14465-74-8 N-phenyl-N-prop-2-ynylamine 
• 107-05-1 3-chloroprop-1-ene 
• 589-09-3 N-allyl-N-phenylamine 
• 106-96-7 propargyl bromide 
• 106-95-6 allyl bromide 

Downstream Products

• 1616405-56-1 (E)-N-((1-allyl-1H-indol-3-yl)methylene)-4-methylbenzenesulfonamide 
• 1616405-48-1 N-allyl-N-((1-tosyl-1H-1,2,3-triazol-4-yl)methyl)aniline 
• 6247-00-3 N,N-diallylaniline 
• 187737-37-7 propene 
• 53146-16-0 tert-butylprop-2-enaldimine 
• 185384-38-7 2,3-dimethoxy-4-hydroxy-4-[3-(N-allyl-N-phenylamino)-1-propynyl]-2-cyclobuten-1-one 
• 50521-41-0 3,4-bis(methylene)-N-phenyl-azolidine 
• 93439-98-6 N-phenyl-N-(prop-2-yn-1-yl)cyanamide 
• 109369-02-0 N,N-diallyl-N-prop-2-ynyl-anilinium; bromide 

Relevant academic research and scientific papers

Efficient method for the synthesis of chiral pyrrolidine derivatives via ring-closing enyne metathesis reaction

(Chemical Equation Presented) A series of new pyrrolidine derivatives were prepared directly in very good yields, from the substrates containing a basic or nucleophilic N atom via ring-closing enyne metathesis reaction under mild reaction conditions. More

Copper(i)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphites

Intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphite diesters proceeded in the presence of Cu(i)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.

Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with diverse carbon pronucleophiles: Facile access to functionalized tetrahydroquinolines

Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with two types of carbon pronucleophiles (nitromethane as a sp3 carbon pronucleophile and phenylacetylenes as sp carbon pronucleophiles) proceeded to give the 2-substituted tetrahydroquinolines in good yields with 100percent atomic utilization without any additional external oxidants.

Synthesis of 2-Indolyltetrahydroquinolines by Zinc(II)-Catalyzed Intramolecular Hydroarylation-Redox Cross-Dehydrogenative Coupling of N-Propargylanilines with Indoles

An intramolecular hydroarylation-redox cross-dehydrogenative coupling (CDC) of propargylic anilines with indoles proceeded in the presence of zinc(II) catalysts to give 2-indolyltetrahydroquinolines in good to high yields. Three C-H bonds (two sp2and one sp3) are activated in one shot and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.

Synthesis of substituted 3-indolylimines and indole-3-carboxaldehydes by rhodium(II)-catalyzed annulation

An efficient Cu/Rh-catalyzed method is proposed for the synthesis of 3-indolylimines from N-propargylanilines through Rh(II)-catalyzed denitrogenative annulation of N-sulfonyl-1,2,3-triazoles. Further combined with hydrolysis or reduction, a one-pot method is developed to enable the direct incorporation of an imine, aldehyde, or amine group into an indole system from an alkyne. A variety of substituted 3-indolylimines, indole-3-carboxaldehydes, and 3-Indolylmethanamines are synthesized in good yields.

Highly selective N-Alkylation of amines promoted on silica: An efficient and recyclable surface

N-Alkylation of amines suffers from competing over alkylations. At the same time, use of strong base and other harsh conditions greatly limits providing a practical, generalized and selective procedure. Activated silica gel has been found to promote N-alkylations of amines. Here, we studied N-alkylation of amines with various types of alkyl halides, which finally constitute practical, highly selective and eco-friendly conditions for mono- or bis-alkylated amines at ambient temperature with recyclability of silica.

Competitive study of Meisenheimer rearrangement in a substrate tertiary amine with allylic and propargylic moieties

A number of allyl aryl propargyl amines 3a-3f were synthesized in 68-82% yield. These tertiary amines were then treated with one equivalent of m-chloroperoxybenzoic acid (m-CPBA) to give products 5a-5f in 79-90% yields arising out of the Meisenheimer rear

Gas-phase thermolysis of N-substituted diallyl- and allylpropargylamines

Various diallyl- and allylpropargylamines were pyrolyzed in a stirred-flow reactor at temperatures in the range of 330-500 °C, pressures of 8-16 Torr and residence times of 0·4-2·4 s using toluene as carrier gas. The reaction products were propene, allene and aldimines. The allene to propene ratio changed considerably with the third substituent on the N atom. At conversions in the range 13-55%, the consumption of the amines showed first-order kinetics. The following Arrhenius parameters [A (s-1) and Ea (kj mol-1)] were obtained from the rate coefficients: diallyl-tert-butylamine, log A = 10·32±0·12, Ea = 139±2; diallylneopentylamine, log A = 12·87±0·26, Ea = 168±3; allylpropargyl-tert-butylamine, log A = 10·23±0·18, Ea = 126±2; allylpropargyltosylamine, log A = 13·05±0.36, Ea = 197±5; and allylpropargylphenylamine, log A = 12·10± 0·35, Ea = 162±4. Polar, six-center cyclic transition states are suggested for the elimination of propene and allene, via non-concerted bond breaking-bond forming mechanisms.