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Article Abstract

Here, we revealed a convenient synthetic protocol for unique pyrido[2,3-]pyridazine and pyrido[3,2-][1,2]oxazine scaffolds with excellent regioselectvity and diastereoselectivity. The functionalized pyrido[2,3-] pyridazines were successfully synthesized via a CsCO-promoted [4 + 2] cycloaddition reaction of α-halogenated tosylhydrazones or acylhydrazones and 5,6-unsubstituted 1,4-dihydropyridines under mild conditions. Additionally, the similar base-promoted [4 + 2] cycloaddition reaction of α-chlorogenated oximes and 5,6-unsubstituted 1,4-dihydropyridines afforded functionalized pyrido[3,2-][1,2]oxazines in satisfactory yields. The features of this reaction included mild reaction conditions, broad substrate scopes, high functional group tolerance, and significant atomic economy.

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http://dx.doi.org/10.1021/acs.joc.4c02525DOI Listing

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