Abstract
2,2-Dialkyl(4-hydroxy-2-butynyl)(3-isopropenylpropargyl)ammonium chlorides in the presence of 0.2 molar equivalents of KOH in water undergo facile cyclization to give 2,2-dialkyl-4-hydroxymethyl-6-methylisoindolinium chlorides, which recyclize to dialkyl(6-methyl-1,3-dihydro-4-isobenzofuranylmethyl)amines by the action of a two-fold molar excess of KOH in water.
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E. O. Chukhajian, A. R. Gevorkyan, El. O. Chukhajian, K. G. Shakhatuni, F. S. Kinoyan, and G. A. Panosyan, Khim. Geterotsikl. Soedin., 34 (2004). [Chem. Heterocycl. Comp., 40, 29 (2004)].
A. R. Gevorkyan, E. O. Chukhajiyan, El. O. Chukhajiyan, and G. A. Panosyan, Khim. Geterotsikl. Soedin., 212 (2004) [Chem. Heterocycl. Comp., 40, 177 (2004)].
E. O. Chukhajian, A. R. Gevorkyan, K. G. Shahkhatuni, H. A. Panosyan, and R. A. Tamazyan, J. Heterocycl. Chem., 40, 1059 (2003).
G. Dupont, R. Dulou, and G. Lefevre, Bull. Soc. Chim. Fr., 816 (1954).
C. Mannich, Ber., 66, 418 (1933).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 528–532, April, 2007.
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Chukhajian, E.O., Nalbandyan, M.K. & Panosyan, G.A. Cyclization of dialkyl(4-hydroxy-2-butynyl)-(3 isopropenylpropargyl)ammonium salts and intramolecular recyclization of the resultant products. Chem Heterocycl Compd 43, 430–433 (2007). https://doi.org/10.1007/s10593-007-0061-6
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DOI: https://doi.org/10.1007/s10593-007-0061-6