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Advisor(s)
Abstract(s)
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].
Description
Keywords
Propargyloxychromones Intramolecular Diels-Alder Flavones Xanthones MW - assisted organic transformations
Pedagogical Context
Citation
Albuquerque, Hélio; Santos, Clementina M.M.; Cavaleiro, José; Silva, Artur (2017). Microwave-assisted synthesis of chromeno[3,4-b]xanthones and (benzo[c]cromenyl)chromones. In TRAMECH IX - Transmediterranean Colloquium on Heterocyclic Chemistry. Fez, Marrocos