Abstract
By triple condensation of thiourea or guanidine with 1,ω-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate first representatives of the new class of ethers bis(benzo)aza-14-crown-4 were obtained in 28–73% yield that included as a subunit a symm-perhydrotriazine ring. This reaction also proceeds readily with N-monomethyl- and N-monopropenyl-substituted thioureas affording the corresponding derivatives of triazinoazacrown ether. At the same time urea in the similar condensation does not form the expected perhydrotriazinoazacrown ether. The molecular structure of one perhydroazacrown ether as a complex with a chloroform molecule was established by XRD analysis.
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Levov, A.N., Strokina, V.M., Komarova, A.I., Le Tuan, An’, and Soldatenkov, A.T., Khim. Geterotsikl. Soedin., 2006, p. 139; Levov, A.N., Le Tuan An’, Komarova, A.I., Strokina, V.M., Soldatenkov, A.T., and Khrustalev, V.N., Zh. Org. Khim., 2008, vol. 44, p. 457; Le Tuan An’, Levov, A.N., Soldatenkov, A.T., and Gruzdev, R.D., Chyong Khong Khieu, Zh. Org. Khim., 2008, vol. 44, p. 463.
Chyong Khong Khieu, Le Tuan An’, Levov, A.N., Nikitina, E.V., and Soldatenkov, A.T., Khim. Geterotsikl. Soedin., 2009, 1747.
Sheldrick, G.M., Acta Cryst., 2008, A64, vol. 112.
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Original Russian Text © Chyong Khong Khieu, A.T. Soldatenkov, Le Tuan An’, A. N. Levov, A.F Smol’yakov, V.N. Khrustalev, M.Yu. Antipin, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 760–763.
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Khieu, C.K., Soldatenkov, A.T., Le Tuan, A. et al. Synthesis and molecular structures of dibenzo(perhydrotriazino)aza-14-crown-4 ethers. Russ J Org Chem 47, 766–770 (2011). https://doi.org/10.1134/S1070428011050174
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DOI: https://doi.org/10.1134/S1070428011050174