Abstract
It was shown that ammonium salts containing a propargyl group together with 3-α-naphthyl-2,3-dichloroallyl or 3-p-tolyl-2,3-dichloroallyl groups undergo cyclization-dehydrochlorination in an aqueous alkaline medium, forming chlorine-substituted naphthisoindolinium and benzisoindolinium salts. If the 3-phenylpropargyl and 3-p-tolyl-2,3-dichloroallyl groups are both present in the molecule of the ammonium salt the latter group enters exclusively into cyclization as diene fragment.
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References
S. T. Kocharyan, V. E. Karapetyan, and N. P. Churkina, Zh. Obshch. Khim., in press.
É. O. Chukhadzhyan, L. A. Manasyan, and A. T. Babayan, Khim. Geterotsikl. Soedin., No. 11, 1481 (1988).
L. A. Kazitsyna and N. B. Kupletskaya, Application of UV, IR, NMR, and Mass Spectroscopy in Organic Chemistry [in Russian], Izd. Mosk. In-ta, Moscow (1979), p. 33.
E. Stern and K. Timmons, Electronic Absorption Spectroscopy in Organic Chemistry [Russian translation], Mir, Moscow (1974), p. 149.
Additional information
Communication 233 of the series “Investigations in the Region of Amines and Ammonium Compounds”. For Communication 232, see [1].
Institute of Organic Chemistry, National Academy of Sciences of the Armenian Republic, Erevan. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1061–1064, August, 1998.
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Chukhadzhyan, É.O., Chukhadzhyan, É.O., Shakhatuni, K.G. et al. Synthesis of chlorine-substituted naphtho- and benzisoindolinium salts by base-catalyzed intramolecular cyclization of ammonium salts. Chem Heterocycl Compd 34, 912–915 (1998). https://doi.org/10.1007/BF02311325
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DOI: https://doi.org/10.1007/BF02311325