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A Divergent Synthesis of Dihydropyridazinones, N-Substituted Dihydropyrazoles, and O-Substituted Pyrazoles

  作者 MASUMOTO EIICHI; MARUOKA HIROSHI; OKABE FUMI; NISHIDA SHO; YOSHIMURA YUKI; FUJIOKA TOSHIHIRO; YAMAGATA KENJI  
  选自 期刊  Journal of Heterocyclic Chemistry;  卷期  2011年48-1;  页码  96-104  
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[摘要]Dihydropyridazinones 4a,b, N-substituted dihydropyrazoles 5b-d, and O-substituted pyrazoles 6a-d have been synthesized starting from spirocyclopropanepyrazole derivative 2. Treatment of 2 with alpha-chloro esters, e.g., methyl chloroacetate, ethyl chloroacetate, isopropyl chloroacetate, and tert-butyl chloroacetate, in potassium carbonate/sodium iodide system caused ring opening and subsequent C- or N-attack nucleophilic substitution to give the corresponding dihydropyridazinones 4a,b and N-substituted dihydropyrazoles 5b-d. On the other hand, in the absence of sodium iodide, O-substituted pyrazoles 6a-d were obtained from 2 via an O-attack nucleophilic substitution.

 
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