Paper
Synthesis of 1H,7H,12bH-Pyrano[3’,4’: 5,6]pyrano[3,4-c][1]benzopyran-1- one via Domino Knoevenagel/Hetero-DielsAlder Reaction with Theoretical Investigations
Published Jan 1, 2012 · M. J. Khoshkholgh, M. R. Hosseindokht, S. Balalaie
Helvetica Chimica Acta
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Abstract
The CuI-catalyzed intramolecular oxa-DielsAlder reaction of 2-(prop-2-yn-1-yloxy)benzaldehydes as unactivated terminal alkynes with 4-hydroxy-6-methyl-2H-pyran-2-one is described. The reaction proceeds with remarkable chemoselectivity to yield pyranones 3 (Scheme 1). A theoretical investigation of the reaction in terms of HOMOLUMO interactions in the gas phase is also reported. The reaction could be regarded as an inverse-electron-demand DielsAlder cycloaddition. The theoretical results are in high agreement with the experimental evidences.
The CuI-catalyzed intramolecular oxa-DielsAlder reaction with 2-(prop-2-yn-1-yloxy)benzaldehydes and 4-hydroxy-6-methyl-2H-pyran-2-one yields pyranones with remarkable che
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