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Sequential multicomponent synthesis of highly functionalized pyridin‐2(1 H )‐one derivatives
Author(s) -
Seixas Raquel S. G. R.,
Ribeiro Gustavo C.,
Guieu Samuel,
Silva Artur M. S.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600080
Subject(s) - chemistry , decarboxylation , amine gas treating , intramolecular force , meldrum's acid , michael reaction , reaction mechanism , ring (chemistry) , acetone , combinatorial chemistry , reaction conditions , organic chemistry , catalysis
Highly functionalized pyridin‐2(1 H )‐one derivatives were synthesized in high yields by a sequential multicomponent reaction. The mechanism involves the Michael addition of Meldrum's acid to 3‐formylchromone, followed by the addition of an amine, intramolecular amidation and elimination of acetone. Depending on the temperature used, decarboxylation can occur. The mechanism of this reaction has been proposed based on the by‐products obtained when the reaction was performed using poorly reactive amines. The versatility of this approach has been exemplified using various 3‐formylchromones and amines. Analogues of Meldrum's acid were also tested, allowing the synthesis of pyridin‐2(1 H )‐one derivatives with various substituents on the aromatic ring.