Literature DB >> 24490591

Metal-free oxidative amidation of 2-oxoaldehydes: a facile access to α-ketoamides.

Nagaraju Mupparapu1, Shahnawaz Khan, Satyanarayana Battula, Manoj Kushwaha, Ajai Prakash Gupta, Qazi Naveed Ahmed, Ram A Vishwakarma.   

Abstract

A novel and efficient method for the synthesis of α-ketoamides, employing a dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions is presented. Furthermore, mechanistic studies supported an iminium ion-based intermediate as a central feature of reaction wherein C1-oxygen atom of α-ketoamides is finally derived from DMSO.

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Year:  2014        PMID： 24490591     DOI： 10.1021/ol5000204

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

2.  Accessing Grignard Reluctant Aldehyde in 2-Oxoaldehyde by Organocuprates to Give [1,2] Addition and Oxidative Coupling Reactions.

Authors:  Satyanarayana Battula; Aman A Desai; Jigar Y Soni; Dhruv P Mehta
Journal:  ACS Omega       Date:  2022-02-01

3.  Oxidative amidation of benzaldehyde using a quinone/DMSO system as the oxidizing agent.

Authors:  Itzel Mejía-Farfán; Manuel Solís-Hernández; Pedro Navarro-Santos; Claudia A Contreras-Celedón; Carlos Jesus Cortés-García; Luis Chacón-García
Journal:  RSC Adv       Date:  2019-06-10       Impact factor: 4.036

4.  PdII-Catalyzed Oxidative Aldehyde-sp2C-H Functionalization and Cyclization Using NHC with Mild Oxidant DMSO for the Selective Synthesis of Esters, Sugar-Based Analogues, and β-Hydroxy Chromanones: An 18O-Labeling Study.

Authors:  Satinath Sarkar; Radha M Laha; Rajendra N Mitra; Dilip K Maiti
Journal:  ACS Omega       Date:  2016-11-21

5.  Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp3)-H amidination.

Authors:  Dianke Xie; Wei He; Jiang Xiao; Yao Wu; Yongjia Guo; Qiang Liu; Cancheng Guo
Journal:  RSC Adv       Date:  2019-03-04       Impact factor: 4.036
  5 in total

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