Abstract
3-Aminoindoles substituted at C-2 and C-5 of the indole ring are converted by the action of Vilsmeier complexes into N-(indol-3-yl)-N′,N′-dialkylamidines. When C-2 is unsubstituted, the formylation proceeds but not the acetylation of this position. N-(Indol-3-yl)-N′,N′-dimethylacetamidine reacts with the complex obtained from DMF and POCl3 to give 2-dimethylamino-3-formyl-δ-carboline. The optimal conditions were found for the conversion of amidines to amides.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 76–81, January, 1985.
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Simakov, S.V., Velezheva, V.S., Kozik, T.A. et al. Synthesis of N-(indol-3-yl)-N′,N′-dialkylamidines by the vilsmeier reaction with 3-aminoindoles. Chem Heterocycl Compd 21, 61–65 (1985). https://doi.org/10.1007/BF00505902
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DOI: https://doi.org/10.1007/BF00505902