98459-41-7

Upstream product

• 108-86-1 bromobenzene 
• 105-56-6 ethyl 2-cyanoacetate 
• 74-88-4 methyl iodide 
• 591-50-4 iodobenzene 
• 1572-99-2 ethyl 2-cyanopropionate 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 6293-66-9 diphenyliodonium p-toluenesulfonate 
• 66003-76-7 Diphenyliodonium triflate 
• 4553-07-5 ethyl phenylcyanoacetate 

Downstream Products

• 1823-91-2 1-phenylethyl cyanide 
• 49683-74-1 3-amino-2-methyl-2-phenyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

Oscillating Emission of [2]Rotaxane Driven by Chemical Fuel

A molecular shuttle consisting of a dibenzo-24-crown-8 macrocycle and an axle with two degenerate peripheral triazolium stations, a central dibenzyl ammonium station, and two anthracenes stoppers was exposed to 2-cyano-2-phenylpropanoic acid as a chemical fuel. Protonation/deprotonation of the amine reversibly switches the rotaxane from a static and little emissive to a dynamic fluorescent shuttling device, the latter exhibiting rapid motion (15 kHz at 25 °C). Four fuel cycles were run.

Tert-Butoxide-Mediated Arylation of 2-Substituted Cyanoacetates with Diaryliodonium Salts

A transition metal-free direct arylation of 2-substituted cyanoacetates with diaryliodonium salts was developed. With this approach, a wide range of α-tolunitrile derivatives has been synthesized in good to excellent yields of 45-92%. Furthermore, the practicability of this approach is further manifested in the synthesis of a related bioactive agent of glutarimide.

AMINOESTER DERIVATIVES

The invention relates to novel compounds which are both phosphodiesterase 4 (PDE4) enzyme inhibitors and muscarinic M3 receptor antagonists, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

Thiazole formation through a modified Gewald reaction

The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.

Cu(I)-catalyzed decarboxylative aldol-type and Mannich-type reactions for asymmetric construction of contiguous trisubstituted and quaternary stereocenters

The catalytic asymmetric decarboxylative aldol-type reaction between aldehydes and cyanocarboxylic acids and Mannich-type reaction between aldimines and cyanocarboxylic acids were developed. α,α,β-Trisubstituted- β-hydroxy nitriles bearing contiguous all-carbon quaternary and trisubstituted stereocenters were produced with moderate enantio- and diastereoselectivity in the presence of 10 mol % CuOAc-TANIAPHOS (or DTBM-SEGPHOS) complex in the aldol-type reaction. α,α,β- Trisubstituted-β-amino nitriles containing contiguous all-carbon quaternary and trisubstituted stereocenters were produced with moderate to high enantio- and diastereoselectivity using 5 mol % CuOAc-(R)-DTBM-SEGPHOS complex in the Mannich-type reaction. These reactions proceed through Cu(I)-catalyzed decarboxylative nucleophile generation, followed by the addition of the resulting chiral Cu-ketenimide to aldehydes or imines. Because the reactions proceed under very mild conditions at nearly neutral pH, the reactions are applicable to a wide range of substrate combinations, including both aromatic and aliphatic substrates. Finally, α,α,β-trisubstituted-β- amino nitriles were converted to β2,2,3-amino acid derivatives through simple acidic hydrolysis without any racemization and epimerization.

Nucleophile generation via decarboxylation: Asymmetric construction of contiguous trisubstituted and quaternary stereocenters through a Cu(I)-catalyzed decarboxylative mannich-type reaction

(Chemical Equation Presented) The first catalytic asymmetric decarboxylative Mannich-type reaction between aldimines and cyanocarboxylic acids was developed. α,α,β-Trisubstituted β-amino nitriles containing contiguous trisubstituted and all-carbon quatern

Palladium-catalyzed one-pot synthesis of 2-alkyl-2-arylcyanoacetates

(Chemical Equation Presented) A one-pot procedure for the synthesis of 2-alkyl-2-arylcyanoacetates based on a Pd(OAc)2/DPPF (DPPF = 1,1′-diphenylphosphino ferreocene)-catalyzed enolate arylation followed by in situ alkylation has been developed. This procedure tolerates a diverse range of aryl and heteroaryl bromides, and provides a rapid entry to a variety of 2-alkyl-2-arylcyanoacetates in good to excellent yield.

Copper-Promoted Reaction of Aryl Iodides with Activated Methine Compounds

The reaction of aryl iodides with an activated methine compound, diethyl acetamidomalonate, can efficiently proceed in the presence of CuI and NaH in DMSO to give diethyl acetamido(aryl)malonates, which may be useful precursors for α-arylglycines, in good

PREPARATION AND SOME REACTIONS OF 4- AND 5-ARYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES

Efficient preparations of 4- and 5-phenyl-4,5-dihydropyridazin-3(2H)-ones have been developed, the main reactions of these compounds have been studied, and the synthetic routes have been used to give analogues with substituents in the phenyl rings.In the best synthesis of the 4-phenyldihyropyridazinone (72 percent overall yield) the product was obtained from phenylacetic acid by three simple stages.This approach was applied in preparations of the 2- and 4-hydroxyphenyl compounds and, in conjunction with a recent method for amine protection, the 4-aminophenyl analogue.A four stage synthesis starting from benzaldehyde gave the 5-phenyldihydropyridazinone in 47 percent overall yield; hydroxybenzaldehydes were similarly converted into 5-(allyloxyphenyl)dihydropyridazinones.Oxidation to phenylpyridazinones occured more readily with the 4- and 5-phenyldihydropyridazinones than with the 6-phenyl isomer.The 4- and 5-dihydropyridazinones were smoothly reduced to tetrahydropyridazinones by hydrogenation over platinum but were uneffected by palladium in the presence of hydrazine or cyclohexene.