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Condensed pyridine bases. Electrophilic substitution in 1,7-dimethyl-3(2H)-benzo[b]furo[2,3-c]pyridone

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Nitration, bromination, thiocyanation, and acylation of 1, 7-dimethyl-3(2H)-benzo[b]furo[2, 3-c]pyridone were investigated. It was shown that either the 4-nitro- or the 4,6-dinitro derivative is formed as a function of the nitration conditions. Bromination with bromine and thiocyanation with dithiocyanogen yields a bromo derivative at position 4. The product of substitution at the C(6), atom is obtained in acylation with acetyl chloride, and the product of substitution at atoms C(4) and C(6) is obtained with benzoyl chloride. The results of the calculations were generalized in the MNDO approximation.

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Authors and Affiliations

  1. L. M. Litvinenko Institute of Physical Organic Chemistry and Carbon Chemistry, National Academy of Sciences of Ukraine, 340114, Donetsk

    S. V. Tolkunov, M. N. Kal'nitskii, S. N. Lyashchuk, S. Yu. Suikov, M. Yu. ubritskii & V. I. Dulenko

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  1. S. V. Tolkunov
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  2. M. N. Kal'nitskii
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  3. S. N. Lyashchuk
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  4. S. Yu. Suikov
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  5. M. Yu. ubritskii
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  6. V. I. Dulenko
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 534–541, April, 1996

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Tolkunov, S.V., Kal'nitskii, M.N., Lyashchuk, S.N. et al. Condensed pyridine bases. Electrophilic substitution in 1,7-dimethyl-3(2H)-benzo[b]furo[2,3-c]pyridone. Chem Heterocycl Compd 32, 466–472 (1996). https://doi.org/10.1007/BF01165914

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  • DOI: https://doi.org/10.1007/BF01165914

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