Conjugate addition of isocyanides to chromone 3-carboxylic acid: an efficient one-pot synthesis of chroman-4-one 2-carboxamides

We report a novel Lewis acid catalysed tandem reaction of isocyanides, chromone 3-carboxylic acid and nucleophiles. An experimentally very simple procedure, involving the use of microwave irradiation in the presence of a Lewis acid catalyst, affords a representative collection of chromone-2-carboxam...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-05, Vol.10 (17), p.3406-3416
Hauptverfasser: Neo, Ana G, Díaz, Jesús, Marcaccini, Stefano, Marcos, Carlos F
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Sprache:eng
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Zusammenfassung:We report a novel Lewis acid catalysed tandem reaction of isocyanides, chromone 3-carboxylic acid and nucleophiles. An experimentally very simple procedure, involving the use of microwave irradiation in the presence of a Lewis acid catalyst, affords a representative collection of chromone-2-carboxamides and chromone-2-carboxamido-3-esters in high yields, in just a few minutes. Such an unprecedented strategy is formally equivalent to a conjugate addition of isocyanides to Michael acceptors.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob07011a