Acta Chimica Sinica ›› 1997, Vol. 55 ›› Issue (2): 202-208. Previous Articles    

Original Articles

若干D环带硝基的小檗因衍生物的光环化合成

叶正区;周启霆   

  1. 中国科学院上海药物研究所
  • 发布日期:1997-02-15

Synthesis of some berbine derivatives with nitro group in ring D via photocyclization

YE ZHENGOU;ZHOU QITING   

  • Published:1997-02-15

Six berbine derivatives 2f~2k with nitro group in ring D have been synthesized via photocyclization 2-methoxy-nitro-benzoyl chlorides reacted with 1-methyl-6,7-dimethoxy (or 6-methoxy-7-benzyloxy)-3,4- dihydro-isoquinolines to give 1-methylene-6,7-dimethoxy (or 6-methoxy- 7-benzyloxy)-N-(2'-methoxy-nitro-benzoyl)-1,2,3,4-tetrahydro- isoquinolines (3) along with unexpected by-products whose structures were identified as 1-methyl-1-(2'-methoxy-benzoyl)-6,7-dimethoxy (or 6-methoxy-7-benzyloxy)-1,2,3,4-tetrahydro-isoquinolines (5). Irradiation of compounds 3 in methanol gave 2,3-dimethoxy (or 2- benzyloxy-3-methoxy) 8-oxo-13,13a-didehydro-berbines (4) with nitro group in ring D and a small amount of corresponding 5. Compounds 4 were treated with POCl3 followed by NaBH4 to afford the berbine derivatives 2f~2k.

Key words: ALKALOID, INFRARED SPECTROPHOTOMETRY, MASS SPECTROGRAPHY, CYCLIZATION, PROTON MAGNETIC RESONANCE SPECTROMETRY

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