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Synthesis of Potentially Bioactive 6-Bromobenzo[f]isoindolinium Bromides by Base-Catalyzed Intramolecular [4+2]-Cycloaddition

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Abstract

Intramolecular cyclization of bromides of diethyl-, dipropyl-, and penthamethylenepropargyl[3-(4-bromophenyl)prop-2-ynyl]ammonium into 6-bromobenzo[f]isoindolinium bromides catalyzed with bases occurs with moderate self-heating. The morpholine analog even in more diluted solutions reacts with vigorous self-heating. Cyclization of dimethyl analog takes place only at heating at 80–85°C during 1 h.

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Authors and Affiliations

  1. Institute of Organic Chemistry of Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    E. O. Chukhadzhian, H. R. Gevorgyan, L. V. Ayrapetyan, El. O. Chukhadzhian, K. G. Shahkhatuni & A. S. Mkrtchyan

  2. Molecular Structure Research Center of Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences of Armenia, Yerevan, 0014, Armenia

    G. A. Panosyan

  3. National Polytechnical University of Armenia, Yerevan, 0009, Armenia

    H. R. Gevorgyan

Authors
  1. E. O. Chukhadzhian
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  2. H. R. Gevorgyan
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  3. L. V. Ayrapetyan
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  4. El. O. Chukhadzhian
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  5. K. G. Shahkhatuni
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  6. A. S. Mkrtchyan
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  7. G. A. Panosyan
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Corresponding author

Correspondence to G. A. Panosyan.

Additional information

Original Russian Text © E.O. Chukhadzhian, H.R. Gevorgyan, L.V. Ayrapetyan, El.O. Chukhadzhian, K.G. Shahkhatuni, A.S. Mkrtchyan, G.A. Panosyan, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 8, pp. 1147–1151.

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Chukhadzhian, E.O., Gevorgyan, H.R., Ayrapetyan, L.V. et al. Synthesis of Potentially Bioactive 6-Bromobenzo[f]isoindolinium Bromides by Base-Catalyzed Intramolecular [4+2]-Cycloaddition. Russ J Org Chem 54, 1156–1160 (2018). https://doi.org/10.1134/S1070428018080067

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  • DOI: https://doi.org/10.1134/S1070428018080067

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