SYNTHESIS OF PYRROLO[2,3-<i>g</i>]- AND PYRROLO[3,2-<i>f</i>]QUINOLINES FROM 5-AMINO-2,3-DIMETHYL- AND 1,2,3-TRIMETHYLINDOLES WITH 4,4,4-TRIFLUOROACETOACETIC ESTER

Authors

  • С. А. Ямашкин Mordovian N. P. Ogarev State University, Saransk 430000
  • Г. А. Романова M. E. Evsev'ev State Teaching Institute, Saransk, 430007
  • Е. А. Орешкина M. E. Evsev'ev State Teaching Institute, Saransk, 430007
  • Н. В. Жукова M. E. Evsev'ev State Teaching Institute, Saransk, 430007

DOI:

https://doi.org/10.1007/8086

Keywords:

5-amino-2, 3-dimethylindole, 5-amino-1, 2, 3-trimethylindole, pyrrolo[2, 3-g]quinoline, pyrrolo[3, 2-f]quinoline, ethyl 4, 4, 4-trifluoroacetoacetate

Abstract

It has been shown that the condensation reaction  of 5-amino-2,3-dimethyl- and 1,2,3-trimethylindoles with 4,4,4-trifluoroacetoacetic ester occurs either  via the trifluoromethylcarbonyl or the ester group depending upon the conditions under which it is carried out. Under thermal conditions (refluxing in diphenyl) the enaminocrotonates formed are readily converted to pyrrolo[3,2-f]quinolines and the amides cyclize in trifluoroacetic acid at 78°C to give pyrrolo[2,3-g]quinolines.

How to Cite
Yamaskhin, S. A.; Romanova, G. A.; Oreshkina, E. A.; Zhukova, N. V.  Chem. Heterocycl. Compd. 2006, 42, 77. [Khim. Geterotsikl. Soedin. 2006, 86.]

For this article in the English edition, see DOI 10.1007/s10593-006-0050-1


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Published

2023-09-22

Issue

No. 1 (2006)

Section

Original Papers