Abstract
The reaction of 2-chloro-5-methylbenzoquinone with Β-aminocrotonic ester derivatives was studied by PMR spectroscopy in CD3COOD. The spectra indicate the formation of intermediate hydroquinone and quinone derivatives, which subsequently transform into the corresponding indoles. It was shown that the indolization proceeds unequivocally at the 3-position of the initial benzoquinone, and the rate of formation of the indole derivatives decreases with increase in the size of the substituent at the nitrogen atom of the Β-aminocrotonic ester. The starting, intermediate compounds and the end products observed in the PMR spectra were identified by comparison with specially synthesized compounds.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 324–328, March, 1990.
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Mikerova, N.I., Alekseeva, L.M., Panisheva, E.K. et al. Reaction of 2-chloro-5-methylbenzoquinone with Β-aminocrotonic ester derivatives. Chem Heterocycl Compd 26, 274–278 (1990). https://doi.org/10.1007/BF00472542
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DOI: https://doi.org/10.1007/BF00472542