abstract
The uncatalyzed reaction of hydrogen peroxide with (E)-3-[3-(2-hydroxyaryl)-3-oxoprop-1-en-1-yl] chromones resulted in a regioselective epoxidation of the chromone intracyclic C(2)= C(3) double bond to afford unique isomeric (E)-7a-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-1aH-oxireno[2,3-b] chromen-7(7aH)-ones in high yields. 2D NMR and single-crystal X-ray diffraction were used to elucidate the structures of the chromanone epoxides. Density functional theoretical studies demonstrated a high electrophilicity of the starting chromones.
keywords
DENSITY-FUNCTIONAL THEORY; ONE-POT SYNTHESIS; HYDROGEN-PEROXIDE; CHROMONE; ENERGY; ACID
subject category
Chemistry
authors
Ameraoui, R; Hammadi, M; Talhi, O; Hassaine, R; Bouchama, A; Abdeldjebar, H; Belmiloud, Y; Brahimi, M; Paz, FAA; Bachari, K; Silva, AMS
our authors
Filipe Alexandre Almeida Paz
Principal Researcheracknowledgements
Thanks are due to University of Aveiro and FCT/MEC for financial support of the QOPNA research project (FCT UID/QUI/00062/2013) and the CICECO-Aveiro Institute of Materials (POCI-01-0145-FEDER-007679; FCT UID/CTM/50011/2013); these are financed by national funds and, when appropriate, co-financed by FEDER under the PT2020 Partnership Agreement, and to the Portuguese NMR Network. We would like also to thank FCT/MEC and the General Directorate for Scientific Research and Technological Development - DGRSDT of Algeria and Agence Thematique de Recherche en Sciences et Technologie ATRST for approving the co-financed bilateral project PTDZ/0005. We further wish to thank CICECO for funding the purchase of the single-crystal X-ray diffractometer.