First intramolecular Diels–Alder reactions using chromone derivatives: synthesis of chromeno[3,4-b]xanthones and 2-(benzo[c]chromenyl)chromones?
New Journal of Chemistry Pub Date: 2018-02-05 DOI: 10.1039/C7NJ05185A
Abstract
A series of novel (E)-2-(2-propargyloxystyryl)chromones and (E,E)-2-[4-(2-propargyloxyphenyl)buta-1,3-dien-1-yl]chromones were designed and synthesized via 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 2-(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 xanthone- and flavone-type compounds.
![Graphical abstract: First intramolecular Diels–Alder reactions using chromone derivatives: synthesis of chromeno[3,4-b]xanthones and 2-(benzo[c]chromenyl)chromones](http://scimg.chem960.com/usr/1/C7NJ05185A.jpg)
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Journal Name：New Journal of Chemistry
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CAS no.: 89640-58-4
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