Abstract
In the condensation of 2-aminoindole with α,Β-unsaturated oxo compounds, in contrast to ordinary aromatic amines and a number of heterocyclic amines, the direction of cyclization is reversed. The general scheme of the reaction includes the reaction of the Β position of 2-aminoindole with the activated double bond of the oxo compound via a mechanism of the Michael type and condensation of the carbonyl group of the unsaturated carboline structure, which subsequently undergoes aromatization. The intermediate 3,4-dihydro-α-carbolines were produced and isolated; this made it possible in a number of cases to establish the structures of the final α-carbolines. The structures of the 3,4-dihydro compounds were confirmed by the set of spectral characteristics. Data from the UV, IR, PMR, and mass spectra are presented.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 945–951, pp. 945–951, July, 1977.
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Sagitullin, R.S., Kost, A.N., Mel'nikova, T.V. et al. Formation of 3,4-dihydro-α-carbolines from 2-aminoindole. Chem Heterocycl Compd 13, 764–769 (1977). https://doi.org/10.1007/BF00470197
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DOI: https://doi.org/10.1007/BF00470197