Sequential multicomponent synthesis of highly functionalized pyridin-2(1H)-one derivatives
authors Seixas, RSGR; Ribeiro, GC; Guieu, S; Silva, AMS
nationality International
journal CHEMISTRYSELECT
author keywords pyridin-2(1H)-one; multicomponent reaction; 3-formylchromone; Meldrum's acid; amine
keywords CONTROL MOLECULAR AGGREGATION; ONE-POT SYNTHESIS; 3-COMPONENT REACTION; NOTHAPODYTINE B; HYDROGEN-BONDS; MELDRUMS ACID; CAMPTOTHECIN; 3-FORMYLCHROMONE; CYCLIZATION; INHIBITORS
abstract Highly functionalized pyridin-2(1H)-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(1H)-one derivatives with various substituents on the aromatic ring.
publisher WILEY-V C H VERLAG GMBH
issn 2365-6549
year published 2016
volume 1
issue 2
beginning page 318
ending page 322
digital object identifier (doi) 10.1002/slct.201600080
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000392471700025
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journal impact factor 1.505
5 year journal impact factor 1.505
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