化学学报 ›› 1966, Vol. 32 ›› Issue (1): 64-67. 上一篇    下一篇

论文

2-乙酰吲哚成及重排

张明哲, 何宗±, 邢其毅   

  1. 北京大学化学系
  • 投稿日期:1965-03-09 发布日期:2013-06-03

SYNTHESIS OF 2-ACETYLINDOLE AND ITS REARRANGEMENT INTO 3-ACETYLINDOLE

CHANG Ming-Che, HE Zong-Shi, HSING Chi-Yi   

  1. Chemistry Department, Peking University
  • Received:1965-03-09 Published:2013-06-03

企图用二乙酰单苯腙在多聚磷酸的作用下,按照Fischer的方法合成2-乙酰吲哚产物不是2-乙酰吲哚是3-乙酰吲哚证明乙酰基的转位,用2-吲哚氮甲基酮催化氢化后所得产物经红外光谱、元素分析及定性方法证明为2-乙酰吲哚产物与多聚磷酸一起加热后,所得产物证实与3-乙酰吲哚同的化合物,因此乙酰基在多聚磷酸的作用下发生转位,由2-位转移到3-位.在多聚磷酸的作用下,乙酰基在吲哚上的转位现象,前人尚无报导.值得在此提出的是Witkop等认为不能用多聚磷酸作缩合剂合成2-位未被取代的吲哚.

An attempt was made to synthesize 2-acetylindole by the conventional Fischer's method from the diacetyl monophenylhydrazone using polyphosphoric acid (PPA) as a condensing agent but the product isolated was proved to be 3-acetylindole.In order to explore the possibility that the migration of the acetyl group from the 2- to the 3-position could take place after the indole formation,the desired 2-acetylindole,which was synthesized by catalytic reduction of the 2-diazo-acetoindole,was treated with PPA,and the expected 3-acetylindole was success fully obtained.The structure of the 2-acetyl tompound was established by its infrared spectrum as well as its derivative formations.Although migration of an alkyl group in the indole ring with PPA as a condensing agent has previously been observed,the authors have not been aware of any migration of an acetyl group up to now.It is interesting to note in this connexion that Witkop and his coworkers have pointed out that "it seems probable that PPA will be useless for the preparation of a 2-unsubstituted indole".