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

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

doi:10.1134/S1070428018080067

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

Authors: Chukhadzhian E.O.¹, Gevorgyan H.R.¹^,2, Ayrapetyan L.V.¹, Chukhadzhian E.O.¹, Shahkhatuni K.G.¹, Mkrtchyan A.S.¹, Panosyan G.A.³
Affiliations:
1. Institute of Organic Chemistry of Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences of Armenia
2. National Polytechnical University of Armenia
3. Molecular Structure Research Center of Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences of Armenia
Issue: Vol 54, No 8 (2018)
Pages: 1156-1160
Section: Article
URL: https://journals.rcsi.science/1070-4280/article/view/218532
DOI: https://doi.org/10.1134/S1070428018080067
ID: 218532

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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.

About the authors

E. O. Chukhadzhian

Institute of Organic Chemistry of Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences of Armenia