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Cyclization of dialkyl(3-phenylpropen-2-yl)-(3-phenylpropyn-2-l)ammonium bromides by the action of an aqueous alkali solution. aqueous-alkaline cleavage of the cyclization products – n,n-dialkyl-4(9)-phenyl-3a,4-dihydro-benzo[f]isoindolinium bromides

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Chemistry of Heterocyclic Compounds Aims and scope

When heated in an alkaline aqueous medium, dialkyl(3-phenylpropen-2-yl)(3-phenylpropyn-2-yl)- ammonium bromides undergo intramolecular cyclization, forming N,N-dialkyl-4(9)-phenyl-3a,4-dihydrobenzo[f]isoindolinium bromides. The cyclization products undergo aqueous-alkaline cleavage at the C(1)–N(2) or N(2)–C(3) bond, which leads to a mixture of 2-(dialkylaminomethyl)-3-methyl- and 3-(dialkylaminomethyl)-2-methyl-1-phenylnaphthalenes. However, only the C(1)–N(2) bond cleavage product is formed in the case of 2,2-pentamethylene-9-phenyl-3a,4-dihydrobenzo-[f]isoindolinium bromide.

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Authors and Affiliations

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

    E. O. Chukhajian, L. V. Ayrapetyan, 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. El. O. Chukhajian
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  4. H. A. Panosyan
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Correspondence to H. A. Panosyan.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1410-1417, September, 2012.

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Chukhajian, E.O., Ayrapetyan, L.V., Chukhajian, E.O. et al. Cyclization of dialkyl(3-phenylpropen-2-yl)-(3-phenylpropyn-2-l)ammonium bromides by the action of an aqueous alkali solution. aqueous-alkaline cleavage of the cyclization products – n,n-dialkyl-4(9)-phenyl-3a,4-dihydro-benzo[f]isoindolinium bromides. Chem Heterocycl Comp 48, 1314–1320 (2012). https://doi.org/10.1007/s10593-012-1138-4

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  • DOI: https://doi.org/10.1007/s10593-012-1138-4

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