83020-34-2

Upstream product

• 513-35-9 2-methyl-but-2-ene 
• 3433-21-4 α-Cyano-α,N-diphenylnitrone 
• 536-74-3 phenylacetylene 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 108-05-4 vinyl acetate 
• 4553-59-7 2-anilino-2-phenylacetonitrile 
• 23269-74-1 1-[1-(phenyl)vinyl]-1H-benzo[d][1,2,3]triazole 
• 1749-19-5 N-(1-phenylethylidene)aniline 
• 7677-24-9 trimethylsilyl cyanide 
• 758640-21-0 N-Benzylaniline 
• 109-77-3 malononitrile 
• 623-49-4 ethyl cyanoformate 
• 32918-05-1 4-hydroxy-3-(2-nitro-1-phenylethyl)-2H-chromen-2-one 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Nitrile compound catalytic synthesis method and application thereof

The invention relates to the technical field of chemical catalytic synthesis, and particularly discloses a nitrile compound catalytic synthesis method and application thereof. According to the nitrile compound catalytic synthesis method, an alpha-aminonitrile or alpha-imino nitrile compound can be synthesized through selective reaction. The nitrile compound catalytic synthesis method has the advantages of simple and easily available raw materials, wide substrate applicability, mild conditions, high yield and the like, the yield is superior to that of a traditional chemical synthesis method, and the nitrile compound catalytic synthesis method is suitable for industrial production. The problems that an existing synthesis method of alpha-aminonitrile and alpha-imino nitrile compounds is not high in yield and does not meet the requirement of green chemistry are solved. Moreover, compared with a traditional chemical synthesis method, a heme system is more efficient and green in use, a substrate is simple and easy to obtain, a tedious catalysis step is not needed, a low-toxicity cyano donor is used, the substrate is wide in applicability, the requirement of green chemistry is met, and the heme system has a wide market prospect.

Nitromethane as a surrogate cyanating agent: 7-: N, N-dimethylamino-4-hydroxycoumarin-catalyzed, metal-free synthesis of α-iminonitriles

An efficient, metal/alkali-cyanide free approach for the synthesis of α-iminonitriles via kinetically controlled, base-mediated and 1,3-diketone-catalyzed reaction is reported. The preparation of target compounds was realized by condensation of substituted anilines and aldehydes in nitromethane as a surrogate cyanating agent and as a solvent. This strategy was further improved by replacing aldehydes and nitromethane with β-nitrostyrene and ethanol, respectively, rendering the methodology greener. The catalytic role played by 1,3-diketones such as 7-N,N-dimethylamino-4-hydroxycoumarin in this three-component reaction was investigated, and a plausible mechanism was proposed based on control experiments.

Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N -Arylenamines

A new method was developed for the synthesis of quinoxalines. This method employs N-arylenamines and TMSN3 as the starting materials and implements two oxidative C-N bond-forming processes in a tandem pattern by using (diacetoxyiodo)benzene as the common oxidant. The present reaction conditions are mild and simple and thus are useful in practical synthesis. (Chemical Equation Presented).

Ambient benzotriazole ring opening through intermolecular radical addition to vinyltriazole

Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode.

Dialkylaminoacetonitrile Derivatives as Amide Synthons. A One-Pot Preparation of Heteroaryl Amides via a Strategy of Sequential SNAr Substitution and Oxidation

Dialkylamino acetonitrile derivatives were utilized as alternative to cyanohydrin synthons for preparation of the corresponding heteroaryl dialkyl amides via a strategy of sequential base-mediated coupling and oxidation. The most advantageous oxidant, NiO2-H2O, can readily oxidize 2-substituted aminoacetonitriles to the corresponding amides under both basic and neutral conditions by forming cyanohydrins in situ.

DDQ-mediated formation of carbon-carbon bonds: Oxidation of imines

The reaction of imines with alkynes and alkenes, in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), to give quinoline derivatives is described. The mechanism of the annulation is discussed, and evidence supporting a non-concerted pathway, at least when the alkene is butyl vinyl ether, is reported. Preliminary information is also given about solid adducts of imines with DDQ, which do not seem to be involved in the reaction path leading to quinolines, and should account for the dependence of product yields on the position of substituents on the starting imines.

Novel Photocycloadditions of Electron-Deficient Nitrones to 2-Methyl-2-butene

In order to decrease the ground state reactivity and increase their potential for cycloadditions, cyano- and methoxycarbonyl-substituted nitrones 1a and 1b, respectively, were prepared and irradiated in the presence of electron-rich alkenes such as 2 to afford the corresponding oxazolidines in which the oxygen atom becomes attached to the least substituted terminus of the olefin and nitrogen attaches the more highly substituted counterpart.While the oxazolidines 12a and 12b obtained from 1b, via the intermediacy of oxaziridine(s) 15 and subsequent N-O bond scission, are isolated and characterized, the oxazolidine(s) 18 formed by cycl ization of 1a are more labile and may undergo ionization to the stabilized oxazolinium ion 19 followed by nucleophilic attack by cyanide ion with accompanying ring opening to afford 6.A sequential diradical mechanism is proposed to rationalize the formation of the observed photoproducts 5 and 6.

PHOTOINDUCED CYCLOADDITIONS OF ELECTRON DEFICIENT NITRONES TO ALKENES

Oxaziridines are proposed as intermediates in the photoinduced cycloadditions of electron deficient nitrones to dipolarophiles.