abstract
Novel furopyran-3,4-dione-fused heterocycles have been obtained by a one-pot reaction of -brominated dehydroacetic acid and benzaldehydes under organobase conditions. The prepared 2-[aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones were fully characterized by 2D NMR spectroscopy and supported by single-crystal X-ray analysis to unequivocally prove the furan-3-one five-membered ring-closure mechanism instead of the dihydroflavanon-3-ol six-membered cyclization which has recently been proposed in the literature.
keywords
STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT APPROACH; DERIVATIVES SYNTHESIS; BIOLOGICAL-ACTIVITY; DEHYDROACETIC ACID; PENICILLIUM-SP; AMINES; CYCLIZATION; FLAVANONES; FLAVONOIDS
subject category
Chemistry
authors
Abdi, Y; Boutemeur-Kheddis, B; Hamdi, M; Talhi, O; Paz, FAA; Kirsch, G; Silva, AMS
our authors
Filipe Alexandre Almeida Paz
Principal Researcheracknowledgements
Thanks are due to the University of Aveiro, Fundacao para a Ciencia e a Tecnologia (FCT, Portugal), EU, QREN, FEDER, COMPETE, for funding the Organic Chemistry Research Unit (project PEstC/QUI/UI0062/2013), and the Portuguese National NMR Network (RNRMN). We would like to thank the General Directorate for Scientific Research and Technological Development-DGRSDT of Algeria for the financial support. O. Talhi also thanks the project New Strategies Applied to Neuropathological Disorders (CENTRO-07-ST24-FEDER-002034), co-funded by QREN, 'Mais Centro-Programa Operacional Regional do Centro' and EU, FEDER for his postdoctoral position. We further wish to thank CICECO Aveiro Institute of Materials (Ref. FCT UID /CTM /50011/2013), financed by national funds through the FCT/MEC, and when applicable co-financed by FEDER under the PT2020 Partnership Agreement, for funding the purchase of the single-crystal X-ray diffractometer.