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Indolopyridines containing a bridgehead heteroatom. 12. Synthesis and reduction of 12-arylidene-5,6-dihydroindolo[2,1-a]isoquinolinium trifluoroacetates

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Abstract

Condensation of 5,6-dihydroindolo[2,1-a]isoquinoline with aromatic aldehydes in trifluoroacetic acid afforded 12-arylidene-5,6-dihydroindolo[2,1-a]isoquinolinium trifluoroacetates. Hydrogenolysis of these salts on rhenium heptasulfide at elevated temperature and hydrogen pressure yielded indolo[2,1-a]isoquinolines, while reduction with sodium borohydride gave 12-arylmethylindoloisoquinolines. Photoluminescence was found for some indolo[2,1-a]isoquinolines.

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Authors and Affiliations

  1. Peoples Friendship University, 3 ul. Ordzhonikidze, 117198, Moscow, Russian Federation

    A. T. Soldatenkov, S. A. Soldatova, Zh. Ntaganda, O. V. Zvolinskii, E. N. Smirnova & M. D. Kharlamova

  2. Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. A. Ryashentseva

Authors
  1. A. T. Soldatenkov
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  2. S. A. Soldatova
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  3. M. A. Ryashentseva
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  4. Zh. Ntaganda
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  5. O. V. Zvolinskii
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  6. E. N. Smirnova
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  7. M. D. Kharlamova
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Soldatenkov, A.T., Soldatova, S.A., Ryashentseva, M.A. et al. Indolopyridines containing a bridgehead heteroatom. 12. Synthesis and reduction of 12-arylidene-5,6-dihydroindolo[2,1-a]isoquinolinium trifluoroacetates. Russian Chemical Bulletin 51, 2116–2120 (2002). https://doi.org/10.1023/A:1021684515325

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