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Synthesis of α‐Substituted Succinimides from Glyoxal and Ketene N , S ‐Acetals
Author(s) -
Xu Qi,
Zheng Baihui,
Pan Ling,
Liu Qun,
Li Yifei
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900520
Subject(s) - chemistry , ketene , glyoxal , intramolecular force , enamine , imine , succinimides , nucleophile , organic chemistry , medicinal chemistry , amine gas treating , formamides , hemiaminal , ugi reaction , hydrolysis , combinatorial chemistry , formamide , catalysis , isocyanide
The reaction of ketene N , S ‐acetals with glyoxal for the efficient synthesis of α‐ketosuccinimides is described. Promoted by concentrated hydrobromide, the reaction proceeded under mild aqueous, metal‐free conditions, with broad substrate tolerance. As a result, one C−C, one C−N, and one C−O bond were formed. Mechanistic studies show that this tandem process involves enamine addition, hydrolysis and intramolecular nucleophilic addition. In the proposed mechanism, the amine released as a byproduct plays a promoter role to accelerate the construction of α‐ketosuccinimides.