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3-Hydroxy-1H-pyrrole

  作者 HILL LAWRENCE; IMAM S HAIDER; MCNAB HAMISH; ONEILL WILLIAM J  
  选自 期刊  Synthesis;  卷期  2009年-15;  页码  2535-2538  
  关联知识点  
 

[摘要]Flash vacuum pyrolysis (FVP) of tert-butyl {[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}acetate at 600 degrees C gives the unstable 3-hydroxy-1H-pyrrole in ca. 55% yield as the only significant product. It exists as the enol tautomer in dimethyl sulfoxide Solution, and predominantly as the keto tautomer in water. 3-Hydroxy-1H-pyrrole reacts readily with mild electrophiles, exclusively at the 2-position. FVP of the product obtained from one Such reaction with methoxymethylene-substituted Meldrum's acid gives pyrano[3,2-b]pyrrol-5(1H)-one in 77% yield.

 
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