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PHOTOINDUCED ELECTRON TRANSFER-INITIATED SELECTIVE CYCLIZATION REACTIONS OF (Z)-N-BENZOYL-alpha-DEHYDRO(1-NAPHTHYL)ALANINAMIDES INTO 4,5-DIHYDROOXAZOLE DERIVATIVES

  作者 SATO YUHKI; YOSHIDA ATSUHIKO; IGARASHI TETSUTARO; SAKURAI TADAMITSU  
  选自 期刊  Heterocycles;  卷期  2010年81-4;  页码  997-1006  
  关联知识点  
 

[摘要]An investigation was undertaken to gain understanding of substituent and solvent effects on the photoreactivity of the title 1-naphthylalanine N',N'-disubstituted amides [(Z)-1] and the (Z)-1-derived product composition. Results indicated that the photoinduced electron transfer reaction of (Z)-1 in methanol containing triethylamine (TEA) proceeds less efficiently than that of the corresponding 1-naphthylalanine alkyl esters to afford cis-4,5-dihydrooxazoles in preference to the trans-isomers and also the former isomers undergo negligible isomerization to the latter isomers in the presence of TEA. Analysis of solvent effects substantiated that both the polarity of solvent and the ability of solvent to donate proton or to accept electron are major factors for controlling the photoreactivity and product composition ratio.

 
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