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An Efficient Intramolecular 1,3-Dipolar Cycloaddition Involving 2-(1,2-Dichlorovinyloxy)aryldiazomethanes: A One-Pot Synthesis of Benzofuropyrazoles from Salicylaldehydes.

  作者 Sales, Zachary S.;Mani, Neelakandha S.;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2009年74-2;  页码  891-894  
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[摘要]A novel intramol. 1,3-dipolar cycloaddn. strategy for a rapid entry into benzofuropyrazoles is described. In a three-step sequence, (E)-2-(1,2-dichlorovinyloxy)aryldiazomethanes were generated in situ from the corresponding salicylaldehydes. Intramol. cycloaddn. followed by dehydrohalogenation garnered 3-chlorobenzofuropyrazoles in excellent yields. By careful choice of solvent, base, and reaction conditions, the entire sequence can be carried out in a one-pot procedure.

 
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