I2/K2CO3-Promoted Ring-opening/Cyclization/Rearrangement/Aromatization Sequence: A Powerful Strategy

来源 :中国化学会第十三届全国有机合成化学学术研讨会 | 被引量 : 0次 | 上传用户:A58400794
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  Furan derivatives are valuable structural motifs as an important class of five-membered containing oxygen heterocycles in both naturally occurring and artificial compounds with their diverse and potent biological properties.Substituted furans also play an important role in synthetic organic chemistry due to their great potential in material science and their usefulness as building blocks.In recent years,D-A cyclopropanes have drawn considerable attention due to the simplicity of their synthesis and potential for variation of the aryl groups,which easily undergo a variety of ring-opening reactions under the influence of a variety of conditions.We have developed a straightforward and efficient approach for the synthesis of alkyl 4-cyanofuran-3-carboxylates via iodine/potassium carbonate-promoted ring-opening/cyclization/rearrangement domino reaction of 1-cyanocyclopropane-1-carboxylates.The operational simplicity,ready availability of reactants,and good chemical yields make this novel synthetic method appealing in diversity-oriented synthesis.This protocol is expected to find considerable applications in the synthesis of polysubstituted furancarboxylates,which are a wide range of structurally interesting and pharmacologically significant compounds.
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