Synthesis of pyrrole derivatives from 5,6-dihydro-4H-1,2-oxazones via reductive deoxygenation by use of Fe3(CO)12.
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概要
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α-Bromooximes such as α-bromoacetophenone oxime and ethyl 3-bromo-2-(hydroxyimino)propanoate react with enamines to give 5,6-dihydro-4<I>H</I>-1,2-oxazines in good yields. Dihydro-1,2-oxazine derivatives are also obtained by the reaction of α-bromooximes with vinyl ethers and silyl enol ethers in the presence of Na<SUB>2</SUB>CO<SUB>3</SUB>. Dihydro-1,2-oxazines can be converted into pyrrole derivatives via reductive deoxygenation by treating with Fe<SUB>3</SUB>(CO)<SUB>12</SUB> in moderate to excellent yields. Iron carbonyl complexes other than Fe<SUB>3</SUB>(CO)<SUB>12</SUB> are also effective for the pyrrole-forming reaction. The efficiency of the complexes for this reaction decreases in the order: Fe<SUB>3</SUB>(CO)<SUB>12</SUB>>>Et<SUB>3</SUB>NH[HFe<SUB>3</SUB>(CO)<SUB>11</SUB>]>Fe<SUB>2</SUB>(CO)<SUB>9</SUB>>>Fe(CO)<SUB>5</SUB>. Both of the dihydro-1,2-oxazine- and pyrrole-forming reactions can be carried out in a single flask, giving pyrrole derivatives in good yields.
- 公益社団法人 日本化学会の論文
著者
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Nakanishi Saburo
Department Of Applied Chemistry College Of Engineering University Of Osaka Prefecture
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Itoh Keiji
Department Of Industrial Chemistry Osaka Prefectural College Of Technology
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Otsuji Yoshio
Department Of Applied Chemistry College Of Engineering University Of Osaka Prefecture
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Hayashi Nobuaki
Department Of Electrical And Electronic Engineering Meijo University
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Hayashi Nobuaki
Department of Industrial Chemistry, Osaka Prefectural College of Technology
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