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Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3‑d]pyridazin-4(5H)‑ones

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journal contribution
posted on 21.08.2015, 00:00 by Mariateresa Giustiniano, Valentina Mercalli, Jussara Amato, Ettore Novellino, Gian Cesare Tron
An expeditious multicomponent reaction to synthesize tetrasubstituted furo­[2,3-d]­pyridazin-4­(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo­[2,3-d]­pyridazin-4­(5H)-ones with an unprecedented level of complexity in a triple domino Diels–Alder/retro-Diels–Alder/lactamization reaction sequence.