81860-68-6

Upstream product

• 59354-24-4 chloroacetonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 14482-11-2 (E)-p-methoxycinnamonitrile 
• 107-14-2 chloroacetonitrile 

Downstream Products

• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 98421-22-8 5-<2-<<2-(4-methoxyphenyl)-2-hydroxy-1-cyanoethyl>amino>ethyl>-8-methoxycarbostyril 
• 344256-01-5 5-(4-Methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile 
• 94592-40-2 5-<2-<<2-(4-methoxyphenyl)ethyl>amino>ethyl>-8-methoxycarbostyril 
• 94592-41-3 8-methoxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>-n-propylamino>ethyl>carbostyril 
• 94592-39-9 5-<2-<<2-(4-methoxyphenyl)-2-hydroxyethyl>amino>ethyl>-8-methoxycarbostyril 
• 94592-43-5 8-hydroxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>amino>ethyl>carbostyril hydrobromide 
• 94592-42-4 8-hydroxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>-n-propylamino>ethyl>carbostyril 
• 104-01-8 4-Methoxyphenylacetic acid 
• 81860-76-6 2-(4-methoxyphenyl)-1-(piperidin-1-yl)ethan-1-one 
• 73377-97-6 (2R,3S)-3-(4-Methoxy-phenyl)-1,2,3,4-tetrahydro-quinoxaline-2-carbonitrile 
• 73384-19-7 (2S,3R)-3-(4-Methoxy-phenyl)-6,7-dimethyl-1,2,3,4-tetrahydro-quinoxaline-2-carbonitrile 

Relevant academic research and scientific papers

BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles

Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.

Concerning the reactivity of dioxiranes. Observations from experiments and theory

The challenging hypothesis of a biphilic (i.e., electrophilic vs nucleophilic) character for dioxirane reactivity, which envisages that electron-poor alkenes are attacked by dioxiranes in a nucleophilic fashion, could not be sustained experimentally. Rate data, which estimate Hammett rho values for the epoxidation of 3- or 4-substituted cinnamonitriles X·Ph-CH=CH-CN, unequivocally allow one to establish that dioxiranes epoxidize electrophilically even alkenes carrying electron-withdrawing-groups. The greater propensity of methyl(trifluoromethyl) dioxirane TFDO (1b) to act as an electrophilic oxidant with respect to dimethyldioxirane DDO (1a) parallels the cathode reduction potentials for the two dioxiranes, as measured by cyclic voltammetry. A simple FMO approach for alkene epoxidation is helpful to conceive a likely rationale for the greater oxidizing power of TFDO as compared to DDO.

REACTION OF 4-SUBSTITUTED BENZALDEHYDES AND ACETOPHENONES WITH CHLOROACETONITRILE

Under conditions of phase-transfer catalysis or in homogeneous solution of potassium tert-butoxide the title compounds give stereoisomeric mixtures of substituted 2,3-epoxy nitriles III and IV.Alkaline hydrolysis of epoxy nitriles IV afforded the corresponding 2-arylpropanals in low yields.On treatment with methanol and potassium carbonate, epoxy nitriles III and IV were converted into epoxy esters in good yields.

Dopamine Receptor Agonist Activity of Some 5-(2-Aminoethyl)carbostyril Derivatives

The potency of β-adrenoreceptor agonists, e.g.,isoproterenol, is strikingly increased by substitution of the meta catecholic hydroxyl group with the NH group of a carbostyril system.To explore the possibility that comparable potency enhacement might occur