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Year 2005, Month 5 (Section Brief Communications, Page 1331)

Synthesis of 2-aryl-6-nitro-4-(vic-triazol-1-yl)-1H-indoles from E-2,4,6-trinitrostilbenes*

O. Yu. Sapozhnikov, V. V. Dyachuk, M. D. Dutov, V. V. Kachala, and S. A. Shevelev

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-20amino-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.

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