The behavior of flavonoid Mannich bases in inverse electron-demand hetero-Diels–Alder reactions was studied. Isoflavones and aurones were used as examples to show that their Mannich bases reacted with 4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)morpholine through an elimination mechanism and subsequent cycloaddition to form derivatives of the new heterocyclic systems pyrano[2′,3′:5,6]chromeno[3,2-c]pyridin-4-one and furo[2′,3′:5,6]chromeno[3,2-c]pyridin-3(2H)-one.
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2016, pp. 859–862.
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Popova, A.V., Mrug, G.P., Kondratyuk, K.M. et al. New Heterocyclic Pyrano[2′,3′:5,6]Chromeno[3,2-c]Pyridin-4-Ones and Furo[2′,3′:5,6]Chromeno[3,2-c]Pyridin-3(2H)-Ones Synthesized Via a Hetero-Diels–Alder Reaction. Chem Nat Compd 52, 1000–1004 (2016). https://doi.org/10.1007/s10600-016-1846-6
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DOI: https://doi.org/10.1007/s10600-016-1846-6