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SYNTHESIS OF ISOCHROMANS BY HYDRIODIC ACID OR IODINE MEDIATED CYCLIZATION REACTIONS OF 1-(2-VINYLPHENYL)PROPAN-2-OLS

  作者 KOBAYASHI KAZUHIRO; SHIKATA KAZUAKI; MAEGAWA HIROKI; FUKAMACHI SHUHEI; TANMATSU MIYUKI; KONISHI HISATOSHI  
  选自 期刊  Heterocycles;  卷期  2010年81-10;  页码  2361-2368  
  关联知识点  
 

[摘要]Treatment of 1-(2-vinylphenyl)propan-2-ols, which can be easily prepared from 2-bromostyrenes and epoxides, with hydriodic acid in acetonitrile yields the corresponding isochromans (1H-3,4-dihydro-2-benzopyrans). When the above alcohols are treated with iodine in acetonitrile in the presence of sodium hydrogencarbonate, the corresponding 1-iodomethylisochromans are obtained, which can be easily converted into the corresponding 1-alkyl(or aryl)sulfanylmethylisochromans on treatment with sodium thiolates in DMF.

 
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