Synthesis of 2-aryl- and 2-hetaryl-4,6-dinitroindoles from 2,4,6-trinitrotoluene

被引：0
|
作者：
Rozhkov, VV
Kuvshinov, AM
Gulevskaya, VI
Chervin, II
Shevelev, SA
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 117913, Russia
[2] Russian Acad Sci, NN Semenov Chem Phys Inst, Moscow 117977, Russia
来源：
SYNTHESIS-STUTTGART | 1999年 / 12期
关键词：
2,4,6-trinitrotoluene; aromatic aldehydes; (E)-stilbenes; aromatic nucleophilic substitution; aromatic azides; 4,6-dinitroindoles;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general preparative method for the synthesis of the previously unknown substituted indoles 2-aryl- and 2-hetaryl-4,6-dinitroindoles from 2,4,6-trinitrotoluene (TNT) has been elaborated. The presented procedure involves condensation of TNT with aromatic and heteroaromatic aldehydes to give the corresponding (E)-stilbenes 1(a-k) and their heterocyclic analogues followed by regiospecific nucleophilic substitution of the ortho-nitro group in 1(a-k) with the azido group under the action of NaN3. The thermolysis of the azides 2(a-k) leads to 2-aryl- or 2-hetaryl-4,6-dinitroindoles 3(a-k).
引用
收藏
页码：2065 / 2070
页数：6
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