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Heterocyclization of 2-acyl-3-indolylacetic acids using hydrazine. Synthesis of 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles

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Chemistry of Heterocyclic Compounds Aims and scope

The heterocyclization of 2-acetyl-3-indolylacetic acid hydrazones and its amides, in contrast to similar derivatives of phenylacetic acid, does not lead to 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino-[4,5-b]indoles but rather to 2-aminoindolo[2,3-c]pyridin-3(2H)-one or azines of 2-acetyl-3-indolyl-acetic acid. 2,3-Dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles were obtained by the reaction of 1-alkylaminoacetylindolo[2,3-c]pyrilium perchlorates and of methyl esters of 2-acetyl- and 2-propionyl-3-indolylacetic acid with hydrazine hydrate.

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Correspondence to V. S. Tolkunov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 907–917, June, 2009.

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Tolkunov, V.S., Eresko, A.B., Khizhan, A.I. et al. Heterocyclization of 2-acyl-3-indolylacetic acids using hydrazine. Synthesis of 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles. Chem Heterocycl Comp 45, 726–734 (2009). https://doi.org/10.1007/s10593-009-0322-7

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  • DOI: https://doi.org/10.1007/s10593-009-0322-7

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