Three different heterocyclic systems, 3-amidocoumarins 1, 3-amidoazacoumarins 11, and N-benzoylindol-2-carboxamides 12 were synthesized based on the strikingly different selectivity of copper-mediated C-O/C-N bond formation from azlactones under conventional heating conditions. The results demonstrated that the stereochemistry of the double bond dictated the outcome of the products. The microwave irradiation played an important role in the isomerization of the trisubstituted olefin leading to the formation of 3-amidocoumarins 1 and 3-amidoazacoumarins 11. Compounds 1h, 1i, and 1l showed promising to good cytotoxic activity against a panel of cancer cell lines including HepG2 (hepatoblastoma) and MOLT-3 (T-lymphoblast acute lymphoblastic leukemia).
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