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Abstract Reaction of an 2-amino-2-ethynylmalonate derivative with an ethynyl sulfone allowed metal-free divergent synthesis of 1,6-dihydropyridines (DHPs) and 3,5-disubstituted pyrroles in one-pot. This facile atom-economical domino process involves hetero-conjugate addition… Click to show full abstract
Abstract Reaction of an 2-amino-2-ethynylmalonate derivative with an ethynyl sulfone allowed metal-free divergent synthesis of 1,6-dihydropyridines (DHPs) and 3,5-disubstituted pyrroles in one-pot. This facile atom-economical domino process involves hetero-conjugate addition and subsequent propargyl aza-Claisen-type rearrangement, followed by either 6π-aza-electrocyclization or 5-exo-dig cyclization. This approach enabled the simple and solvent-dependent divergent syntheses of densely functionalized 1,6-DHPs and pyrroles at ambient temperature.
Journal Title: Tetrahedron Letters
Year Published: 2021
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