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Efficient and Practical One-Pot Conversions of N-Tosyltetrahydroisoquinolines into Isoquinolines and of N-Tosyltetrahydro-beta-carbolines into beta-Carbolines through Tandem beta-Elimination and Aromatization

  作者 DONG JING; SHI XIAOXIN; YAN JINGJING; XING JING; ZHANG QIANG; XIAO SEN  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-36;  页码  6987-6992  
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[摘要]An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-beta-carbolines (N-tosyl-THBCs) into beta-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-beta-carbolines as intermediates, and these were then oxidized in situ by molecular oxygen to furnish isoquinolines or beta-carbolines in good to high yields. Both one-pot conversions occurred through tandem beta-elimination and aromatization.

 
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