resumo
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.
palavras-chave
CONTROL MOLECULAR AGGREGATION; ONE-POT SYNTHESIS; 3-COMPONENT REACTION; NOTHAPODYTINE B; HYDROGEN-BONDS; MELDRUMS ACID; CAMPTOTHECIN; 3-FORMYLCHROMONE; CYCLIZATION; INHIBITORS
categoria
Chemistry
autores
Seixas, RSGR; Ribeiro, GC; Guieu, S; Silva, AMS
nossos autores
Samuel Jacques André Guieu
Investigador Júnioragradecimentos
Thanks are due to University of Aveiro, FCT/MEC for the financial support to the QOPNA research Unit (FCT UID/QUI/00062/2013), through national funds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement, and also to the Portuguese NMR Network. R.S.G.R. Seixas and S. Guieu also thank to FCT for their post-doctoral grants (SFRH/BPD/74282/2010 and SFRH/BPD/70702/2010, respectively).