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Condensed pyridine bases. Reactions of 1-oxo-3,3,6-trimethyl-1,2,3,4-tetrahydrobenzo[b]furo-, benzo[b]thieno-, and indolo[2,3-c]quinolines with electrophilic reagents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A study has been made of thenitrationand bromination of 1-oxo-3,3,6-trimethyl-1,2,3,4-tetrahydrobenzo[bjfuro-, benzo[b]thieno-, and indolo[2,3-c]quinolines. It has been shown that the nitration is directed to the benzene ring (position 10). Bromination by molecular bromine takes place at the 6-CH3 group of the pyridine fragment and yields a mixture of the corresponding nwnobromomethyl and dibromomethyl derivatives, whereas a dimethylacetamide-bromine complex bronzinates the methylene group in position 2, forming the α-bromoketone. The Schmidt reaction of 1-oxo-3,3,6-trimetliyl-1,2,3,4-tetrahydrobenzo[b]furo-, benzol[b]thieno-, and indolo[2,3-c]quinolines have been investigated, as well as conversions of their oximes under conditions of the Beckmann rearrangement.

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Authors
  1. S. V. Tolkunov
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  2. M. N. Kal'nitskii
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  3. A. I. Khizhan
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  4. S. Yu. Suikov
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  5. M. Yu. Zubritskii
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  6. V. I. Dulenko
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Additional information

L. M. Litvinenko Institute of Physical Organic Chemistry and Coal Tar Chemistry, National Academy of Sciences of the Ukraine, Donetsk 340114. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1124–1130, August, 1995. Original article submitted December 30, 1994; revision submitted May 28, 1995.

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Tolkunov, S.V., Kal'nitskii, M.N., Khizhan, A.I. et al. Condensed pyridine bases. Reactions of 1-oxo-3,3,6-trimethyl-1,2,3,4-tetrahydrobenzo[b]furo-, benzo[b]thieno-, and indolo[2,3-c]quinolines with electrophilic reagents. Chem Heterocycl Compd 31, 980–986 (1995). https://doi.org/10.1007/BF01170326

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  • DOI: https://doi.org/10.1007/BF01170326

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