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Base-Promoted Formal [3 + 2] Cycloaddition of α-Halohydroxamates with Carbon Disulfide to Synthesize Polysubstituted Rhodanines.

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A concise and practical strategy via potassium-carbonate-mediated [3 + 2]-cycloaddition reaction of α-halohydroxamates with the common solvent carbon disulfide for the synthesis of functionalized rhodanine derivatives in good to excellent… Click to show full abstract

A concise and practical strategy via potassium-carbonate-mediated [3 + 2]-cycloaddition reaction of α-halohydroxamates with the common solvent carbon disulfide for the synthesis of functionalized rhodanine derivatives in good to excellent yields is developed. The present methodology features a wide substrate scope as well as good functional group tolerance. The potential synthetic utility of this protocol is demonstrated by synthesis of a series of natural product derivatives containing rhodamine skeletons.

Keywords: base promoted; promoted formal; carbon disulfide; cycloaddition halohydroxamates; formal cycloaddition; cycloaddition

Journal Title: Organic letters
Year Published: 2022

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