A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid.: Application of the methodology as a convenient route to benzimidazoles
A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid.: Application of the methodology as a convenient route to benzimidazoles
复制标题
DOI：
10.1016/s0040-4020(00)01158-3
复制
发表时间：
2001-02-25
期刊：
影响因子：
2.1
通讯作者：
Gilchrist, TL
中科院分区：
文献类型：
--
作者：
Fonseca, T;Gigante, B;Gilchrist, TL
甲基顺式-deisopropyldehydroabietate选择性硝化在12-位通过与“粘土”，蒙脱石粘土浸渍硝酸铜（II）的反应。将12-硝基化合物还原成相应的胺，并将其进行酰化和邻位硝化的组合。如此产生的化合物通过还原环化进一步转化为八氢-1H-菲并[2，3-d]咪唑。相同的酰化-邻位硝化方法被证明提供了从苯胺短合成2-取代的苯并咪唑。(C)2001爱思唯尔科技有限公司版权所有。
Methyl cis-deisopropyldehydroabietate was selectively nitrated at the 12-position by reaction with 'claycop', a montmorillonite clay impregnated with copper(II) nitrate. The 12-nitro compound was reduced to the corresponding amine and this was subjected to a combined acylation and ortho nitration. The compounds so produced were further converted into octahydro-1H-phenanthro[2,3-d]imidazoles by reductive cyclization. The same acylation-ortho nitration methodology was shown to provide a short synthesis of 2-substituted benzimidazoles from aniline. (C) 2001 Elsevier Science Ltd. All rights reserved.