Synthesis of 2-aryl-6-nitro-4-(<Emphasis Type="Italic">vic</Emphasis>-triazol-1-yl)-1<Emphasis Type="Italic">H</Emphasis>-indoles from <Emphasis Type="Italic">E</Emphasis>-2,4,6-trinitrostilbenes |
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Authors: | O Yu Sapozhnikov V V Dyachuk M D Dutov V V Kachala S A Shevelev |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | A method is developed for the preparation of 4-(vic-triazol-1-yl)indoles that involves replacement of the ortho-NO2 group in E-2,4,6-trinitrostilbenes by an azido group, condensation of E-2-azido-4,6-dinitrostilbenes with acetylacetone, replacement of the second ortho-NO2 group in the resulting stilbenes by N3, and subsequent thermolysis of the azide into the target indole. The reactions of E-2-azido-4,6-dinitrostilbenes with cyclohexane-1,3-dione gave E-2-amino-4,6-dinitrostilbenes, which can be used for selective transformation of the ortho-NO2 group into an amino group in E-2,4,6-trinitrostilbenes.
Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1293–1296, May, 2005. |
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Keywords: | indoles E-2 4 6-trinitrostilbenes 2 4 6-trinitrotoluene nucleophilic substitution of the nitro group azides 1 2 3-triazoles 1 3-dipolar cycloaddition intramolecular cyclization diazo transfer |
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