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Chemistry of Heterocyclic Compounds

, Volume 46, Issue 7, pp 859–867 | Cite as

Synthesis and alkylation of 4-aryl-5-oxo-1h-2,3,4,5-tetrahydroindeno[1,2-b]pyridines*

  • S. Stupnikova
  • E. Petushkova
  • D. Tanajev
  • V. LusisEmail author
  • D. Muceniece
Article

Reduction of 5-oxo-4-phenyl-1H-4,5-dihydroindeno[1,2-b]pyridines with triethylsilane in trifluoro-acetic acid gave the corresponding 1,2,3,4-tetrahydroindeno[1,2-b]pyridines predominatly with the trans-configured substituents at atoms C(2), C(3), and C(4). Alkylation of the anionic form of the tetrahydroindenopyridines gives the N- and C(4a)-alkyl derivatives.

Keywords

5-oxo-4,5-dihydro-1H- and 2,3,4,5-tetrahydro-1H-indeno[1,2-b]pyridines N- and C(4a)- alkylation of 5-oxo-2,3,4,5-tetrahydro-1H-indeno[1,2-b]pyridine triethylsilane reduction 

References

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    U. Rosentreter, Synthesis, 210 (1985).Google Scholar
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    C. Taberez, V. Waterman, A. L. Rapp, P. Moyna, and G. Moyna, Tetrahedron Lett., 50, 7128 (2009).CrossRefGoogle Scholar
  3. 3.
    D. Muceniece, S. Stupnikova, and V. Lusis, Khim. Geterotsikl. Soedin., 1071 (2001). [Chem. Heterocycl. Comp., 37, 982 (2001)].Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • S. Stupnikova
    • 1
  • E. Petushkova
  • D. Tanajev
    • 1
  • V. Lusis
    • 1
    Email author
  • D. Muceniece
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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