72811-88-2

Upstream product

• 935-02-4 3-Phenyl-2-propynonitrile 
• 62-53-3 aniline 
• 17196-74-6 (Z)-3-amino-3-phenylacrylonitrile 
• 142-04-1 aniline hydrochloride 
• 614-16-4 Benzoylacetonitrile 
• 33665-93-9 2,2-dioxo-6-phenyl-2,3-dihydro-2λ⁶-[1,2,3]oxathiazin-4-one 
• 72827-13-5 4-Chloro-6-phenyl-[1,2,3]oxathiazine 2,2-dioxide 
• 72827-20-4 (E)-3-phenyl-3-(phenylamino)acrylonitrile 

Downstream Products

• 1088711-65-2 C₁₅H₁₄N₂ 

Relevant academic research and scientific papers

Preparation method of beta-amino acrylonitrile compounds

The invention discloses a preparation method of beta-amino acrylonitrile compounds. Beta-aminocyanoacrylate represented by formula I reacts in a solvent under the action of a catalyst to obtain the beta-aminoacrylonitrile compounds represented by formula II; and in the formulas, R is a C1-C12 alkyl group, a halogenated C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C2-C12 alkenyl group, a C2-C12 alkynyl group, an aryl group, a substituted aryl group, a benzyl group or a substituted benzyl group, and R is hydrogen, halogen, a hydroxyl group, an amino group, a cyano group, a nitro group,a C1-C12 alkyl group or a halogenated C1-C12 alkyl group. The method has the characteristics of good stereoselectivity, high yield, simplicity preparation of the raw material beta-aminocyanoacrylate,and great practical value.

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.

Asymmetric reduction of imines with trichlorosilane, catalyzed by sigamide, an amino acid-derived formamide: Scope and limitations

(Chemical Equation Presented) Enantioselective reduction of ketimines 6-10 with trichlorosilane can be catalyzed by the N-methyl valine-derived Lewis-basic formamide (S)-23 (Sigamide) with high enantioselectivity (≤97% ee) and low catalyst loading (1-5 mol %) at room temperature in toluene. The reaction is efficient with ketimines derived from aromatic amines (aniline and anisidine) and aromatic, heteroaromatic, conjugated, and even nonaromatic ketones 1-5, in which the steric difference between the alkyl groups R1 and R 2 is sufficient. Simple nitrogen heteroaromatics (8a,b,d) exhibit low enantioselectivities due to the competing coordination of the reagent but increased steric hindrance in the vicinity of the nitrogen (8c,e) results in a considerable improvement. Cyclic imines 32d-d exhibited low to modest enantioselectivities.

Dynamic kinetic resolution in the asymmetrie synthesis of β-amino acids by organocatalytic reduction of enamines with trichlorosilane

A new methodology based on the organocatalytic asymmetric hydrosilylation of enamines that allows a direct access to a range of β3 and β2.3-amino acid derivatives was presented. The results show a successful reduction of aromatic substrates, a sterically more hindered ortho-substituted derivatives, and the thiophenyl analogue exhibiting lower reactivity. Fast enamine-imine equilibration is crucial as imines are chiral but racemic, while α-alkyl β-amino acids can be accessed by the symmetrical Mannich reaction. The α-alkyl derivatives have relative and absolute configuration due to their reduction with LiAlH4 into a known amino alcohols. Predominant formation of the anti isomer in 3o is consistent with conformation of the imine intermediate in the catalytic reduction.

E/Z Photoisomerization of 3-Amino-3-phenylprop-2-enenitriles

The E/Z photoisomerization of 3-phenyl-3-(N-substituted amino)- and 3-phenyl-3-(N,N-disubstituted amino)-prop-2-enenitriles was investigated by means of u.v. and 13C n.m.r. spectroscopy.Informative results on the mechanism of the reaction produced by direct irradiation of 3-anilino-3-phenylprop-2-enenitrile were obtained from the different effects of quenchers and heavy atoms.Neither the heavy atoms nor the quenchers had any effect on direct photoisomerisation, which involves only the singlet state, by-passing the triplet state.