Polysubstituted 2,3-dihydrofuro[2,3-b]pyridines and 3,4-dihydro-2H-pyrano[2,3-b]pyridines via microwave-activated inverse electron demand Diels-Alder reactions |
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Authors: | Youssef Hajbi,Franck Suzenet,Mostafa Khouili,Gé rald Guillaumet |
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Affiliation: | a Institut de Chimie Organique et Analytique (ICOA), UMR-CNRS 6005, University of Orléans, France b Laboratoire de Chimie Organique et Analytique, University Cadi-Ayyad, Béni-Mellal, Morocco c Laboratoire de Biochimie, Environnement et Agroalimentaire, University of Hassan II-Mohammedia, Morocco |
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Abstract: | Polysubstituted 2,3-dihydrofuro[2,3-b]pyridines and 3,4-dihydro-2H-pyrano[2,3-b]pyridines have been synthesized from 1,2,4-triazines using the inverse electron Diels-Alder reaction. For this purpose, 3-methylsulfanyl-1,2,4-triazines were reacted with several nucleophiles allowing the formation of appropriately substituted alkynes to undergo the intramolecular inverse electron demand Diels-Alder reaction. Sealed-tube microwave activation of the cycloaddition reaction has proved to be very efficient and allowed shorter reaction times. This strategy enabled an efficient synthesis of 3-hydroxy-2,3-dihydrofuro[2,3-b]pyridines and 4-hydroxy-3,4-dihydro-2H-pyrano[2,3-b]pyridines with several points of diversity on the bicyclic scaffold. |
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