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

Authors

  • С. В. Толкунов L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 340114 Donetsk
  • M. Н. Кальницкий L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 340114 Donetsk
  • C. Н. Лящук L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 340114 Donetsk
  • С. Ю. Суйков L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 340114 Donetsk
  • М. Ю. Зубрицкий L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 340114 Donetsk
  • В. И. Дуленко L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 340114 Donetsk

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.

How to Cite
Tolkunov, S. V.; Kal'nitskii, M. N.; Lyashchuk, S. N.; Suikov, S. Yu.; Zubritskii, M. Yu.; Dulenko, V. I. Chem. Heterocycl. Compd. 1996, 32, 466. [Khim. Geterotsikl. Soedin. 1996, 534.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01165914

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Published

1996-04-25

Issue

No. 4 (1996)

Section

Original Papers