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Synthesis of 6-Bromo-3a,4-dihydrobenzo[f]isoindolinium Bromides and Their Aqueous-Alkaline Cleavage

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Abstract

Cyclization of allyl[3-(4-bromophenyl)prop-2-ynyl]ammonium bromides under basic catalysis conditions, unlike their propargyl analogs, occurs under heating of the reaction mixture at 90–92°C. Cyclization, which is the main reaction route, is accompanied by rearrangement-cleavage to form 1-allyl-p-bromocinnamaldehyde. A favorable effect of the substituents on the nitrogen atom and the presence of the bromine atom in the 4 position of the aromatic ring on the cyclization and rearrangement-cleavage reactions is established.

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Authors and Affiliations

  1. The Institute of Organic Chemistry of the Scientific Technological Centre of Organic and Pharmaceutical Chemistry of NAS of Republic of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    E. O. Chukhajian, L. V. Ayrapetyan, H. S. Mkrtchyan, El. O. Chukhajian & H. A. Panosyan

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  1. E. O. Chukhajian
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  2. L. V. Ayrapetyan
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  3. H. S. Mkrtchyan
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  4. El. O. Chukhajian
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  5. H. A. Panosyan
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Correspondence to L. V. Ayrapetyan.

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The authors declare no conflict of interest.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 8, pp. 1215–1222.

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Chukhajian, E.O., Ayrapetyan, L.V., Mkrtchyan, H.S. et al. Synthesis of 6-Bromo-3a,4-dihydrobenzo[f]isoindolinium Bromides and Their Aqueous-Alkaline Cleavage. Russ J Org Chem 55, 1124–1130 (2019). https://doi.org/10.1134/S1070428019080104

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  • DOI: https://doi.org/10.1134/S1070428019080104

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