Synthesis of Cyclopentadiene-Fused Chromanones via One-Pot Multicomponent Reactions

We have developed one-pot method for the synthesis of functionalized novel cyclopentadiene-fused chromanone scaffolds. A variety of 4-oxo-2,4-dihydro­cyclopenta[c]chromene-1,2-dicarboxylates were obtained in moderate to good yields via condensation of 2-hydroxybenzaldehydes and ethyl acetoacetate wi...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-03, Vol.78 (6), p.2611-2616
Main Authors: Ghandi, Mehdi, Ghomi, Ali-Tabatabaei, Kubicki, Maciej
Format: Article
Language:English
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Summary:We have developed one-pot method for the synthesis of functionalized novel cyclopentadiene-fused chromanone scaffolds. A variety of 4-oxo-2,4-dihydro­cyclopenta[c]chromene-1,2-dicarboxylates were obtained in moderate to good yields via condensation of 2-hydroxybenzaldehydes and ethyl acetoacetate with 1:1 acetylenecarboxylate–isocyanides in toluene. These reactions presumably proceed via reaction of the in situ generated 3-acetyl-2H-chromen-2-ones with acetylenecarboxylate–isocyanide zwitterionic intermediates through Michael addition/intramolecular cyclization and double [1,5] acyl shift rearrangement cascade.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo302790y