One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine
Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).
Golub, Tatiana,Dou, Gui-Yuan,Zeng, Cheng-Chu,Becker, James Y.
p. 7961 - 7964
(2019/10/11)
Nitrile Additions to C,N-Diacylimines. Formation of 4-Amidooxazoles
Nitriles are shown to react with C,N-diacylimines 2, generated in situ from 1 or 4 in the presence of Lewis acids, to produce 4-amidooxazoles 5 and 6 in good to excellent yield.Diamides are sometimes also produced.The reaction was followed by NMR spectros
Fischer, Bilha,Hassner, Alfred
p. 5225 - 5229
(2007/10/02)
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