Microwave-assisted synthesis of chromeno[3,4-b]xanthones and (benzo[c]cromenyl)chromones
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abstract
Following previous reports dealing with the reactivity of chromone derivatives in Diels-Alder
reactions, series of novel (E)-2-[2-(prop-2-yn-1-yloxy)styryl]chromones and of 2-{(1E,3E)-4-[2-
(prop-2-yn-1-yloxy)phenyl]buta-1,3-dien-1-yl}chromones were designed and synthesized
through aldol condensation of 2-methylchromones with 2-propargyloxy(benzaldehyde and
cinnamaldehyde), respectively. Both chromone derivatives were used as substrates in
microwave-assisted intramolecular Diels-Alder reactions, affording chromeno[3,4-b]xanthones
and (benzo[c]chromenyl)chromones. This is the first report involving chromone derivatives in
intramolecular Diels-Alder reactions for the synthesis of new oxygen heterocycles, namely
xanthones and flavones [1-2].
Two series of novel
propargyloxychromones were
designed and synthesized. Both
chromone derivatives were used
as substrates in MW-assisted
intramolecular Diels-Alder
reactions, affording
chromeno[3,4-b]xanthones and
(benzo[c]chromenyl)chromones.
This is the first report involving
chromone derivatives in
intramolecular Diels-Alder
reactions for the synthesis of
new oxygen heterocycles,
namely xanthones and flavones.
