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Issue 6, 2018
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First intramolecular Diels–Alder reactions using chromone derivatives: synthesis of chromeno[3,4-b]xanthones and 2-(benzo[c]chromenyl)chromones

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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

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Publication details

The article was received on 30 Dec 2017, accepted on 05 Feb 2018 and first published on 05 Feb 2018


Article type: Paper
DOI: 10.1039/C7NJ05185A
Citation: New J. Chem., 2018,42, 4251-4260
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    First intramolecular Diels–Alder reactions using chromone derivatives: synthesis of chromeno[3,4-b]xanthones and 2-(benzo[c]chromenyl)chromones

    H. M. T. Albuquerque, C. M. M. Santos, J. A. S. Cavaleiro and A. M. S. Silva, New J. Chem., 2018, 42, 4251
    DOI: 10.1039/C7NJ05185A

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