Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom