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Versatile and Sustainable Synthesis of Cyclic Imides from Dicarboxylic Acids and Amines by Nb 2 O 5 as a Base‐Tolerant Heterogeneous Lewis Acid Catalyst
Author(s) -
Ali Md. Ayub,
Siddiki S. M. A. Hakim,
Kon Kenichi,
Hasegawa Junya,
Shimizu Kenichi
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404538
Subject(s) - catalysis , lewis acids and bases , chemistry , reagent , hydroxylamine , base (topology) , organic chemistry , lewis acid catalysis , ammonia , condensation , mathematical analysis , physics , mathematics , thermodynamics
Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom‐efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb 2 O 5 as a reusable and base‐tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N ‐hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.