Visible-Light-Mediated Synthesis of Amides from Aldehydes and Amines via in Situ Acid Chloride Formation
An efficient visible-light photocatalysis-based one-pot amide synthesis method was developed; visible-light irradiation of a mixture of an aldehyde, tert-butyl hydrogen peroxide, and N-chlorosuccinimide using a Ru(bpy)3Cl2 photocatalyst afforded an acid chloride, which subsequently reacted with amine to yield the corresponding amide. The reaction was used to synthesize moclobemide and a D3 receptor intermediate.
Iqbal, Naeem,Cho, Eun Jin
p. 1905 - 1911
(2016/03/15)
Chloroform as a Carbon Monoxide Precursor: In or Ex Situ Generation of CO for Pd-Catalyzed Aminocarbonylations
Conditions for the rapid hydrolysis of chloroform to carbon monoxide (CO) using heterogeneous CsOH·H2O are described. CO and 13CO can be generated cleanly and rapidly under mild conditions and can be captured either in or ex situ in palladium-catalyzed aminocarbonylation reactions. Utilizing only 1-3 equiv of CO allows for the aminocarbonylation of aryl, vinyl, and benzyl halides with a wide variety of primary and secondary amines giving amide products in good to excellent yields. (Chemical Equation Presented).
Gockel, Samuel N.,Hull, Kami L.
supporting information
p. 3236 - 3239
(2015/07/15)
Direct amide synthesis from equimolar amounts of carboxylic acid and amine catalyzed by mesoporous silica SBA-15
Direct amide synthesis from equimolar amounts of carboxylic acid and amine using mesoporous silica as a versatile heterogeneous catalyst is reported.
Tamura, Mizuki,Murase, Daisuke,Komura, Kenichi
supporting information
p. 769 - 776
(2015/03/14)
Mesoporous niobium oxide spheres as an effective catalyst for the transamidation of primary amides with amines
Mesoporous niobium oxide spheres (MNOS), conveniently prepared by a novel antisolvent precipitation approach, have been shown to be an effective catalyst for the transamidation of primary amides with amines. This novel transamidation can be efficiently carried out under solvent-free conditions and is applicable to a wide range of primary amides and amines to provide N-alkyl amides in good to excellent yields. The catalyst is highly stable and reusable. The application of this transamidation reaction has been demonstrated in the synthesis of antidepressant drug moclobemide and other druglike compounds.
Ghosh, Subhash Chandra,Li, Cheng Chao,Zeng, Hua Chun,Ngiam, Joyce S. Y.,Seayad, Abdul M.,Chen, Anqi
p. 475 - 484
(2014/05/20)
Nucleophilic Ring Opening of 2-Oxazolines with Amines: A Convenient Synthesis for Unsymmetrically Substituted Ethylenediamines
The reaction of 2-alkyl-2-oxazolines with alkyl- and arylamines was investigated.The acid-catalyzed nucleophilic ring opening of the 2-oxazolines yields N-(2-aminoethyl)carboxamides in good to excellent yields with secondary amines and hindered primary amines.The N-(2-aminoethyl)carboxamides were hydrolyzed under acidic or basic conditions to selectively yield unsymmetrically substituted ethylenediamines.
Fazio, Michael J.
p. 4889 - 4893
(2007/10/02)
Basicity, lipophilicity, and lack of receptor interaction of N-aminoalkylbenzamides and N-aminoalkyl-o-anisamides as model compounds of dopamine antagonists
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Anker,Testa,Van de Waterbeemd,et al.
p. 542 - 556
(2007/10/02)
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