Abstract
By application of acid-catalyzed condensation of propane-2-, benzene- and methanesulfonamides with glyoxal a series of new derivatives of oxaazaisowurtzitanes were obtained, in particular, new heterocyclic systems: 2,4,6,8,12-pentaoxa-10-aza- and 2,4,8,12-tetraoxa-6,10-diazatetracyclo[5.5.0.03,11.05,9]-dodecanes.
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Kleinschmidt, E. and Wanninger, P., FRG Patent no. 4324739, 1994.
Clement, D., Koch, E.-C., Rudolf, K., Eigenmann, B., 10th Seminar “New Trends in Research of Energetic Materials”, Pardubice, Czech Republic, 25–27 April, 2008, p. 128.
Radacsi, N., Bouma, R.H.B., Krabbendamla Haye, E.L.M., ter Horst, J.H., Stankiewicz, A.I., and van der Heijden, A.E.D.M., Propellants, Explos., Pyrotech., 2013, vol. 38, p. 761.
Risse, B., Schell, F., and Spitzer, D., Propellants, Explos., Pyrotech., 2014, vol. 39, p. 391.
Doherty, R.M. and Watt, D.S., Propellants, Explos., Pyrotech., 2008, vol. 33, p. 4.
Borne, L., Mory, J., and Schlesser, F., Propellants, Explos., Pyrotech., 2008, vol. 33, p. 37.
Sakovich, G.V., Sysolyatin, S.V., Kozyrev, N.V., Makarovets, N.A., RF Patent no. 2252925, 2003.
Nielsen, A.T., US Patent no. 5693794, 1997.
Nielsen, A.T., Chafin, A.P., Christian, S.L., Moore, D.W., Nadler, M.P., Nissan, R.A., and Vanderah, D.J., Tetrahedron, 1998, vol. 54, p. 11793. doi 10.1016/S0040-4020(98)83040-8
Piacenza, G., Blaive, B., Gallo, R., and Jacob, G., 28th International Annual Conference of ICT, Combustion and Detonation, Karlsruhe, Germany, 24–27 June, 1997, p. 123/1.
Walsh, M.E., Jenkins, T.F., and Thorne, P.G., J. Energ. Mater., 1995, vol. 13, p. 357.
Bircher, H.R., Maeder, P., and Mathieu, J., 29th Proceedings of International Annual Conference of ICT, Karlsruhe, Germany, 1998, p. 94/1.
Stepanov, R.S. and Kruglyakova, L.A., Russ. J. Gen. Chem., 2010, vol. 80, p. 316. doi 10.1134/S1070363210020210
Gatilov, Yu.V., Rybalova, T.V., Efimov, O.A., and Lobanova, A.A., J. Struct. Chem., 2005, vol. 46, p. 566. doi 10.1007/s10947-006-0141-y
Vagenknecht, J., Marecek, P., and Trzcinski, W.A., J. Energ. Mater., 2002, vol. 20, p. 245.
Koch, E.-C., Prop. Explos. Pyrotech., 2015, vol. 40, p. 374.
Sysolyatin, S.V., Sakovich, G.V., Chernikova, Y.T., Surmachev, V.N., and Lobanova, A.A., 37th International Annual Conference of ICT, Karlsruhe, Germany, 27–30 June, 2006, p. 141.
Ramakrishnan, V.T., Vedachalam, M., and Boyer, J.H., Heterocycles, 1990, vol. 31, p. 479.
Highsmith, T.K., Edwards, W.W., and Wardle, R.B., US Patent no. 5498711, 1996.
Ghaderia, H., Zolfigol, M.A., Bayat, Y., Zareia, M., and Noroozizadeha, E., Synlett., 2016, vol. 27, p. 2246.
Sysolyatin, S.V., Lobanova, A.A., and Chernikova, Y.T., International Conference “Modern Problems of Organic Chemistry”, Novosibirsk, 27–30 September, 2001, p. 104.
Sysolyatin, S.V., Surmachev, V.N., Lobanova, A.A., Chernikova, Y.T., and Sakovich, G.V., 5th International Conference & Exhibit “High Energy Materials”, DRDL, Hyderabad, 23–25 November, 2005, p. 101.
Kerscher, T., Klapotke, T., Krumm, B., Polborn, K., and Scherr, M., J. Fluor. Chem., 2006, vol. 127, p. 1030.
Kalashnikov, A.I., Sysolyatin, S.V., and Shein, N.V., Polzynovskii Vestn., 2013, p. 42.
Sysolyatin, S.V., Kalashnikov, A.I., Lobanova, A.A., Chernikova, Yu.T., and Kadulin, V.V., RF Patent no. 2355693, 2009.
Paromov, A.E., Sysolyatin, S.V., and Gatilov, Y.V., J. Energ. Mater., 2017, vol. 35, p. 363.
Paromov, A.E., Abstracts of Papers, V Vserossiiskaya nauchno-tekhnicheskaya konferentsiya molodykh uchonykh, “Perspektivy sozdaniya i primeneniya kondensirovannykh vysokoenergeticheskikh materialov” (Vth All-Russian Scientific Conf. of Young Scientists “Perspectives of Creation and Application of Condensed High-energy Materials”), IPKhET SO RAN, 11-12 September, 2014, Biisk: Izd. Altais. Gos. Tekhn. Univer., p. 35.
Klages, F., Jung, H.A., and Hegenberg, P., Chem. Ber., 1966, vol. 99, p. 1701.
Yang, K., Ke, M., Lin, Y., and Song, Q., Green Chem., 2015, vol. 17, p. 1395.
Zhou, Y., Li, L., Webber, S.E., Dragovich, P., Murphy, D.E., Tran, C.V., Zhao, J., and Ruebsam, F., WO Appl. no. 2008082725, 2008.
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Original Russian Text © A.E. Paromov, S.V. Sysolyatin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 11, pp. 1680–1688.
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Paromov, A.E., Sysolyatin, S.V. Synthesis of new N-polysubstituted oxaazaisowurtzitanes by acid-catalyzed condensation of sulfonamides with glyoxal. Russ J Org Chem 53, 1717–1725 (2017). https://doi.org/10.1134/S1070428017110197
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DOI: https://doi.org/10.1134/S1070428017110197