879552-29-1Relevant academic research and scientific papers
Synthesis of 2-aryl- and 2-hetaryl-4-6-dinitroindoles from 2,4,6- trinitrotoluene
Rozhkov, Vladimir V.,Kuvshinov, Alexander M.,Gulevskaya, Valentina I.,Chervin, Ivan I.,Shevelev, Svyatoslav A.
, p. 2065 - 2070 (1999)
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 susbtitution 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).
