Base-Promoted Formal [3 + 2] Cycloaddition of α-Halohydroxamates with Carbon Disulfide to Synthesize Polysubstituted Rhodanines
Xiaoqiang Lei, Juan Feng, Qing‐Lan Guo, Chengbo Xu, Jian‐Gong Shi
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.
Topics & Concepts
ChemistryRhodanineCarbon disulfideCycloadditionPotassium carbonateCombinatorial chemistrySubstrate (aquarium)Organic chemistryCatalysisGeologyOceanographyStructural and Chemical Analysis of Organic and Inorganic CompoundsSynthesis and Biological EvaluationSynthesis of heterocyclic compounds