Formation of basic compounds during the indole cyclization of ketone phenylhydrazones
作者:Caterina Canu Boido、Vito Boido、Federica Novelli、Fabio Sparatore
DOI:10.1002/jhet.5570350412
日期:1998.7
occasional findings, the Fischer indole cyclization of ten ketone phenylhydrazones containing moieties of increasing bulkiness was investigated in order to isolate eventual side products. In the cases of the three 2-, 3- and 4-acetylpyridine phenylhydrazones the corresponding 2-pyridylindoles were the sole compounds so far isolated. In all the remaining cases, beside the indoles a mixture of basic compounds
根据以前的偶然发现,为了分离最终的副产物,对十个含有增加体积的部分的酮苯hydr进行了Fischer吲哚环化研究。在三个2-,3-和4-乙酰基吡啶苯并azo的情况下,相应的2-吡啶基吲哚是迄今为止唯一的化合物。在所有其余情况下,除了吲哚以外,还获得了碱性化合物的混合物。在所有情况下苯胺和2-取代的(2-甲基或2-苯基)苯并咪唑形成,通过明显的最后所得邻苯腙的-semidinic重排。由甲基异丙基酮苯基hydr开始,式C 11 H 15的化合物还分离出NO,基于ir,nmr光谱和化学反应性将3-(4-氨基苯基)-3-甲基丁酮的结构分配给该NO。该化合物的形成似乎与苯基的对-联苯胺样重排有关。