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Reaction of 1,3-oxathin-6-ones with bases: synthesis of 4-mercapto-2-pyrone.

  作者 Okuma, Kentaro;Koda, Masahiro;  
  选自 期刊  Heterocycles;  卷期  2008年75-3;  页码  571-576  
  关联知识点  
 

[摘要]The reaction of 4-phenyl-1,3-oxathiin-6-one 3,3-dioxide (I) with secondary amines gave cinnamamides and ammonium sulfinates. On with LDA, followed by addn. of benzoyl chloride, gave II (R = CH2COPh) and its isomer (III) in nearly a 1:1 ratio, whereas the reaction with 1-benzoyl-1,2,3-benzotriazole gave only II (R = CH2COPh) in 78% yield. Thermolysis of II (R = CH2COPh) gave 4-mercapto-2-pyrone IV in 62% yield.

 
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