Abstract
The Vilsmeier-Haack reaction with 1H,6H-pyrrolo[2,3-e]indole with the participation of dimethylacetamide was studied. 3-Acetyl, 8-acetyl, 2-acetyl, and 3,8-diacetyl derivatives (with great preponderance of the 3-acetyl derivative) were obtained. The formation of a 2-substituted product does not have an analogy in the chemistry of indole. On the basis of data from the IR and PMR spectra it was established that an intramolecular hydrogen bond between 1-H and the C=O group in the 8 position exists in the 8-acetylpyrroloindole molecule. This bond also affects the mass-spectral fragmentation of the 8-acetyl derivative.
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See [1] for communication 4.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 206–211, February, 1982.
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Samsoniya, S.A., Targamadze, N.L., Kozik, T.A. et al. Pyrroloindoles. 5. Acetylation of 1H,6H-pyrrolo[2,3-e]indole by means of the Vilsmeier-Haack reaction. Chem Heterocycl Compd 18, 158–163 (1982). https://doi.org/10.1007/BF00512961
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DOI: https://doi.org/10.1007/BF00512961