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Base-catalyzed Intramolecular Diels–Alder Cyclization of Dialkyl(3-arylprop-2-yn-1-yl)-(3-phenylprop-2-en-1-yl)ammonium Bromides in Aqueous Solution

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Chemistry of Heterocyclic Compounds Aims and scope

Dialkyl(3-arylprop-2-yn-1-yl)(3-phenylprop-2-en-1-yl)ammonium bromides, in contrast to their allyl analogs containing a 3-arylprop-2-en-1-yl group, undergo cyclization in aqueous solution in the presence of base upon prior heating to give potentially biologically active 2,2-dialkyl-6-chloro-4-phenyl-3a,4-dihydrobenzo[f]isoindolinium bromides in almost quantitative yield. Heat is released in the course of these reactions. We found that the introduction of a phenyl group at position 3 of the allyl fragment facilitates the cyclization. This is the first report of a base-catalyzed intramolecular cyclization of allyl analogs of dialkyl(3-arylprop-2-yn-1-yl)ammonium salts.

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Authors and Affiliations

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

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

Authors
  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 L. V. Ayrapetyan.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1367-1374, September, 2013.

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Chukhajian, E.O., Ayrapetyan, L.V., Chukhajian, E.O. et al. Base-catalyzed Intramolecular Diels–Alder Cyclization of Dialkyl(3-arylprop-2-yn-1-yl)-(3-phenylprop-2-en-1-yl)ammonium Bromides in Aqueous Solution. Chem Heterocycl Comp 49, 1274–1280 (2013). https://doi.org/10.1007/s10593-013-1375-1

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