32852-95-2Relevant academic research and scientific papers
HIGHLY REGIOSELECTIVE AROMATIC SUBSTITUTION ON A DIARYLOXIDETRICARBONYLCHROMIUM COMPLEX
Boutonnet, Jean-Charles,Rose-Munch, Francoise,Rose, Eric
, p. 3989 - 3992 (1985)
Ortho-substituted diaryloxide tricarbonylchromium (0) complexes PhOAr-Cr(CO)3, treated with carbanions Nu(-), give, after acid quenching, paradisubstituted complexes NuAr-Cr(CO)3 via a 1,3-hydride migration followed by elimination of phenol: the overall sequence of the reaction consists in a regioselective meta substitution of the phenoxy group by the nucleophile.
Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides
Chen, Ying,Xu, Lanting,Jiang, Yongwen,Ma, Dawei
supporting information, p. 7082 - 7086 (2021/02/26)
α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.
Method for synthesizing arylpropionic acid-like nonsteroidal antiinflammatory agent
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Paragraph 0037-0040, (2017/10/27)
The invention discloses a method for synthesizing an arylpropionic acid-like nonsteroidal antiinflammatory agent. The method comprises that an aryl acetonitrile compound as a substrate, an amine borane complex and N, N-dimethylformamide as a solvent undergo a methylation reaction under basic conditions to produce an aryl propionitrile compound, and the aryl propionitrile compound is hydrolyzed under strong basic conditions to form the arylpropionic acid-like nonsteroidal antiinflammatory agent. The method creatively uses the amine borane complex and N, N-dimethylformamide as methylation reagents so that bis-methylation and large toxicity caused by the traditional methylation reagents such as methyl iodide and dimethyl sulfate are avoided. The method is simple and is easy to operate. The arylpropionic acid-like nonsteroidal antiinflammatory agent has a high yield and high purity. Compared with the existing method using a metal catalyst system, the method utilizes anon-metallic system so that the use of transition metals is avoided. The method provides a novel approach for preventing metal residues in synthetic drugs.
Molecular Orbital and Experimental Studies on the Photoinduced Decarboxylation of Pyrethroid Model Esters
Katagi, Toshiyuki,Mikami, Nobuyoshi,Matsuda, Tadashi,Miyamoto, Junshi
, p. 779 - 782 (2007/10/02)
A series of pyrethroid model esters with various substituents in the acid or alcohol moiety have been irradiated by u. v.-radiation (λ > 220 nm).The main reaction is decarboxylation, as evidenced by gas chromatographic (g. c.) and mass spectrometric (m. s.) analyses.In the photoinduced decarboxylation reaction, the substituent effect on the main transition, which occurs via carbonyl excitation, and on the reactivity of a radical intermediate have been examined by semiempirical molecular-orbital calculations (MNDO and CNDO/S).It has been found tha the change of benzyl carbon-oxygen bond strength in the excited states is one of the important factors in determining the yield of the decarboxylated product.
Alpha-thio-alpha-aryl-substituted alkanonitrile and process for preparing alpha-aryl-substituted alkanonitrile therefrom
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, (2008/06/13)
An alpha-thio-alpha-aryl-substituted alkanonitrile of the general formula STR1 wherein Ar represents an aromatic group, R represents a hydrogen atom or an alkyl group, R1 represents an alkyl group or an aromatic group, and Y represents an oxygen atom or a carbonyl group. The above compound can be prepared by reacting an alpha-aryl-substituted-alpha-thio-acetonitrile of the general formula STR2 wherein Ar, Y and R1 are as defined above, with an alkylating agent in the presence of a strong base. This compound is useful as an intermediate for producing an alpha-aryl-substituted alkane-carboxylic acid of the general formula STR3 wherein Ar, Y and R1 are as defined above.
