Copper-Mediated [3+2] Oxidative Cyclization of N-Tosylhydrazones and β-KetoestersSynthesis of 2,3,5-

来源 :第五届岭南有机化学论坛暨华南理工大学-兰州大学有机化学双边论坛 | 被引量 : 0次 | 上传用户:jihuoxiazai
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Furans are a ubiquitous structural motif in numerous naturally occurring products[1],synthetic pharmaceuticals[2],agrochemicals,and also useful building blocks in organic synthesis[3].In recent years,N-tosylhydrazones,derived easily from the corresponding ketones,have been widely explored in building various cyclic products by furnishing diverse structure modules as synthons.As our particular interests in using N-tosylhydrazones as two-carbon synthons to construct active structural motifs via cyclization reactions,herein,we propose a copper-mediated [3+2] oxidative cyclization to synthesize 2,3,5-trisubstituted furans from N-tosylhydrazones and β-ketoesters.This process is thought to construct C-C and C-O bonds through the oxidative cyclization of vinyl copper species and β-ketoesters free radical intermediates[4].To the best of our knowledge,this is the first attempt utilizing N-tosylhydrazones compounds as building blocks to synthesize furans.The studies provide important complementary approaches for synthesizing substituted furans.
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