70625-63-7Relevant articles and documents
Green and efficient synthesis method for aryl acrylonitrile compound
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Paragraph 0031; 0033; 0035; 0036; 0091; 0094, (2018/07/07)
The invention discloses a green and efficient synthesis method for an aryl acrylonitrile compound represented by formula III. The method comprises the following steps: in an air atmosphere, by takingaryl acetonitrile of formula I as shown in the specification and excess methyl cyanoacetate of formula II as shown in the specification as raw materials, and Ru/C as a catalyst, enabling the components to react at 150-160 DEG C in the absence of a solvent, and separating and purifying a reaction mixture obtained after the reaction is completed, thereby obtaining an aryl acrylonitrile compound of formula III as shown in the specification. The method disclosed by the invention is not only low in production cost, but also good in environment protection, and is very applicable to industrial large-scale production.
Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to arylmethylene cyanoacetates
Soegel, Sebastian,Tokunaga, Norihito,Sasaki, Keigo,Okamoto, Kazuhiro,Hayashi, Tamio
, p. 589 - 592 (2008/04/12)
Asymmetric 1,4-addition of arylboronic acids to (￡)-methyl 2-cyano-3-arylpropenoates proceeded in the presence of a rhodium catalyst (3 mol %) coordinated with a chiral diene ligand, (R,R)-Ph-bod*, to give high yields of the corresponding methyl 3,3-diaryl-2-cyanopropanoates with high enantioselectivity (up to 99% ee). This catalytic asymmetric transformation was applied to the asymmetric synthesis of (R)-tolterodine. American Chemical Society.
Research and development of an efficient process for the construction of the 2,4,5-substituted pyridines of NK-1 receptor antagonists
Harrington, Peter J.,Johnston, Dave,Moorlag, Henk,Wong, Jim-Wah,Hodges, L. Mark,Harris, Les,McEwen, Gerald K.,Smallwood, Blair
, p. 1157 - 1166 (2012/12/23)
Roche has identified a 2,4,5-trisubstituted pyridine template for a new class of potent NK1 receptor antagonists. Previous strategies for construction of the pyridine core of these NK-1 receptor antagonists involved functionalization of a 2,5-disubstituted pyridine. We now report on construction of the pyridine core from commodity components. Shestopalov reported the synthesis of trans-4′-aryl-5′-cyano-1′,2′,3′, 4′-tetrahydro-6′-hydroxy-2′-oxo-1,3′-bipyridinium inner salts from 1-(2-amino-2-oxo-ethyl)pyridinium chloride, aromatic aldehydes, and ethyl cyanoacetate in the presence of a base. Reaction of these salts with phosphorus oxychloride affords 4-aryl-3-cyano-2,6-dichloropyridines. These are efficiently converted to nicotinamide precursors of the Roche NK-1 receptor antagonists by regioselective displacement of one chlorine by an amine, hydrogenolysis of the remaining chlorine, and nitrile hydrolysis.
