Abstract
O-Methyl-4-coumarincarbaldehyde oxime reacted as an azadiene with electron-deficient and electron-rich dienophiles to give, via one-step hetero-Diels–Alder cycloaddition reactions, the corresponding 5 H-coumarin[4,3- c]pyridin-5-ones. When excess of the dienophile was used, fused azatetracyclo derivatives were also formed via a tandem Diels–Alder and 1,3-dipolar cycloaddition reaction of the dienophile to an azomethine ylide formed by the intermediate 2,3-dihydro-5 H-coumarin[4,3- c]pyridine-5-one. The regio- and stereoselectivities of the new compounds correspond well with spectroscopic (2D NMR) and theoretical data. A possible mechanistic scheme is provided.
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