Condensed pyridine bases. Reactions of 1-oxo-3,3,6-trimethyl-1,2,3,4-tetrahydrobenzo[<i>b</i>]furo-, benzo[<i>b</i>]thieno-, and indolo[2,3-<i>c</i>]quinolines with electrophilic reagents
Abstract
A study has been made of the nitration and bromination of 1-oxo-3,3,6-trimethyl-1,2,3,4-tetrahydrobenzo[b]furo-, 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 monobromomethyl and dibromomethyl derivatives, where as a dimethylacetamide-bromine complex brominates 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.
How to Cite
Tolkunov, S. V.; Kal'nitskii, M. N.; Khizhan, A. I.; Suikov, S. Yu.; Zubritskii, M. Yu.; Dulenko, V. I. Chem. Heterocycl. Compd. 1995, 31, 980. [Khim. Geterotsikl. Soedin. 1995, 1124.]
For this article in the English edition, see DOI https://doi.org/10.1007/BF01170326
