Efficient synthesis of pyrano[2,3-c]coumarins via intramolecular domino Knoevenagel hetero-Diels-Alder reactions |
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| Authors: | Malihe Javan Khoshkholgh Saeed Balalaie Frank Rominger |
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| Affiliation: | a Department of Chemistry, K.N. Toosi University of Technology, PO Box 15875-4416, Tehran, Iran
b Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120, Heidelberg, Germany |
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| Abstract: | The domino Knoevenagel hetero-Diels-Alder reaction of the O-propargylated salicylaldehydes and 4-hydroxycoumarin leads to pyrano[2,3-c]coumarins 3 and pyrano[2,3-c]chromones 4 in high yield in the presence of CuI as a Lewis acid. In all cases, the reaction was shown to exhibit high regioselectivity and form product 3 as main product. |
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| Keywords: | Alkynes Domino reactions Cycloadditions Oxygen heterocycles Copper catalysis |
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