51991-49-2

Upstream product

• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 552-89-6 2-nitro-benzaldehyde 
• 773837-37-9 sodium cyanide 
• 253684-24-1 1-(2,2-dibromovinyl)-2-nitrobenzene 
• 107-14-2 chloroacetonitrile 
• 1466-88-2 2-nitrocinnamic aldehyde 
• 1885-38-7 cinnamic nitrile 
• 4360-47-8 cinnamonitrile 
• 1466-88-2 2-nitrocinnamaldehyde 
• 39909-23-4 o-Nitro-zimtaldehyd-oxim 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 75-05-8 acetonitrile 
• 4336-70-3 (cyanomethyl)triphenylphosphonium chloride 
• 39909-23-4 2-nitro-cinnam-syn-aldoxime 

Downstream Products

• 53093-52-0 C₁₈H₁₂N₄O 
• 51991-54-9 (E)-3-(2-Hydroxyamino-phenyl)-acrylonitrile 
• 58106-57-3 (E)-3-(2-aminobenzene)acrylonitrile 
• 55000-16-3 3-(2-aminophenyl)propionitrile 
• 580-22-3 2-aminoquinoline 
• 30958-68-0 2-Amino-chinolin-1-oxid 
• 72844-86-1 (E)-N-(2-(2-cyanovinyl)phenyl)acetamide 
• 51796-65-7 3-iodo-1H-indole-2-carbonitrile 

Relevant academic research and scientific papers

Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes

β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

A useful method for the conversion of olefins to nitro olefins

Triflyl nitrate is easily generated from tetra-n-butylammonium nitrate in CH2Cl2 solution and serves as an effective nitrating agent for a wide range of unsaturated substrates to form nitro olefins.

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source

The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.

Aerobic Copper-Promoted Radical-Type Cleavage of Coordinated Cyanide Anion: Nitrogen Transfer to Aldehydes to Form Nitriles

We have disclosed for the first time the copper-promoted C≡N triple bond cleavage of coordinated cyanide anion under a dioxygen atmosphere, which enables a nitrogen transfer to various aldehydes. Mechanistic study of this unprecedented transformation suggests that the single electron-transfer process could be involved in the overall course. This protocol provides a new cleavage pattern for the cyanide ion and would eventually lead to a more useful synthetic pathway to nitriles from aldehydes.

Cross-Cycloaddition of Two Different Isocyanides: Chemoselective Heterodimerization and [3+2]-Cyclization of 1,4-Diazabutatriene

A new cross-cycloaddition reaction between a wide range of isocyanides and 2-isocyanochalcones (or analogues) was developed for the expeditious synthesis of pyrrolo[3,4-b]indoles under thermal conditions. On the basis of the experimental results and DFT c

CUCN-MEDIATED ONE POT PRODUCTION OF CINNAMONITRILE DERIVATIVES

The present invention discloses a cheaper and practical protocol for the construction of a wide variety of o-cyanocin-namonitrile and their structural analogues that proceeds with good yields in a single step using CuCN as the only reagent.

Dual [Fe+Phosphine] catalysis: Application in catalytic wittig olefination

Iron hydride complexes of the general formula P2Fe(NO)CO)H are highly active catalysts for the hydrosilylation of aldehydes or ketones and phosphine oxides. Depending on the solvent, the in situ reduction of the phosphine oxide can be faster than the corresponding hydrosilylation of a carbonyl group. This unusual activity was used within the context of catalytic Wittig olefination. Picture perfect: Iron hydride complexes of the general formula P2Fe(NO)CO)H are highly active catalysts for the hydrosilylation of aldehydes or ketones and phosphine oxides. Depending on the solvent, the in situ reduction of the phosphine oxide can be faster than the corresponding hydrosilylation of a carbonyl group. This unusual activity is used within the context of catalytic Wittig olefination. EWG=Electron-withdrawing group.

Cu-catalyzed debrominative cyanation of gem-dibromoolefins: A facile access to α,β-unsaturated nitriles

An efficient catalytic route for the synthesis of α,β-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed. The method utilized inexpensive reagents such as Cu2O as a catalyst, l-proline as a ligand and NaCN as a cyanide source to afford α,β-unsaturated nitriles in high yields (62-86%). A deuterium exchange study has shown that one of the bromide atoms of gem-dibromoolefins exchanges with cyanide while the other with a deuterium atom.

Wittig Olefination Using Phosphonium Tetraphenylborate in the Absence of Additional Base

The thermal decomposition of (substituted methyl)triphenylphosphonium tetraphenylborates, which can also be generated in situ from the corresponding phosphonium halide and NaBPh4, with an aldehyde affords olefins in 22-100% yields. This Wittig olefination does not need use additional base to form phosphorus ylide, and is highly tolerant of benzoic acid.

CUCN-MEDIATED ONE POT PRODUCTION OF CINNAMONITRILE DERIVATIVES

The present invention discloses a cheaper and practical protocol for the construction of a wide variety of o-cyanocinnamonitrile and their structural analogues that proceeds with good yields in a single step using CuCN as the only reagent.