22745-35-3Relevant academic research and scientific papers
Reductive Alkylation of α-Keto Imines Catalyzed by PTSA/FeCl3: Synthesis of Indoles and 2,3′-Biindoles
Naidu, P. Seetham,Kolita, Sinki,Sharma, Meenakshi,Bhuyan, Pulak J.
, p. 6381 - 6390 (2015/06/30)
A simple and efficient method for the synthesis of highly functionalized indoles and biindoles was developed. In the reaction protocol, three components were used in one pot and products were obtained in high yield in an easy workup procedure. The reactio
α-Carbonylimine to α-Carbonylamide: An efficient oxidative amidation approach
Padala, Anil K.,Mupparapu, Nagaraju,Singh, Deepika,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
, p. 3577 - 3586 (2015/06/08)
Abstract Our interest in generating amide bonds by employing the activated C=N system has led to the development of an efficient oxidative amidation reaction between 2-oxoaldehyde and weak nucleophilic amines (anilines, benzamides and sulfonamides). Mechanistic studies support the involvement of α-carbonylimine (-CO-C=N-) based compounds or intermediates as a central feature of the reaction, in which an adjacent CO moiety enhances the electrophilicity of the C=N system, which favors attack of the oxidant (TBHP or SeO2), thereby resulting in the generation of the desired products in good yields. The direct oxidative coupling of 2-oxoaldehydes and weak nucleophilic amines has been accomplished through either MgSO4-TBHP-pyridine/CuBr, or SeO2·pyridine promoted methods. In the current study, SeO2·pyridine emerged as a versatile reagent with which to promote initial α-carbonylimine formation between 2-oxoaldehyde and weak nucleophilic amine, and subsequent oxidation to the corresponding α-carbonylamide. The reported methodology constitutes one of the few reports of the synthesis of α-ketoamides from anilines, perhaps the second report for the generation of α-ketoimides, and the first report of the generation of 2-oxoamides with sulfonamides.
