A novel method has been developed for preparation of substituted 4H-3,1-benzoxazines via formation of tetrafluoroborates. The substitution of halogen in 2-(α-haloalkyl)-4,4-diphenyl-4H-3,1-benzoxazines by NH and SH nucleophiles was performed. The effect of electrophilic substitution in the annelated aromatic ring in a series of 2,4-substituted 4H-3,1-benzoxazines has been studied.
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E. V. Gromachevskaya, A. S. Pilipenko, A. V. Butin, V. E. Zavodnik, and G. D. Krapivin, Khim. Geterotsikl. Soedin., 125 (2010). [Chem. Heterocycl. Comp., 46, 106 (2010)].
E. V. Gromachevskaya, F. V. Kvitkovskii, T. P. Kosulina, and V. G. Kul’nevich, Khim. Geterotsikl. Soedin., 161 (2003). [Chem. Heterocycl. Comp., 39, 137 (2003)].
N. V. Kolotova, V. O. Koz’minykh, E. V. Dolbilkina, E. N. Koz’minykh, V. E. Kolla, and S. A. Shelenkova, Khim.-Farm. Zh., No, 9, 32 (1998).
S. S. Mochalov, R. A. Gazzaeva, A. N. Fedotov, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 922 (2003). [Chem. Heterocycl. Comp., 39, 794 (2003)].
E. V. Gromachevskaya, T. P. Kosulina, and V. G. Kul’nevich, Khim. Geterotsikl. Soedin., 537 (1993). [Chem. Heterocycl. Comp., 29, 460 (1993)].
E. V. Gromachevskaya, T. P. Kosulina, A. L. Chekhun, and V. G. Kul’nevich, Khim. Geterotsikl. Soedin., 542 (1993). [Chem. Heterocycl. Comp., 46, 465 (1993)].
V. G. Kul’nevich, E. V. Gromachevskaya, and T. P. Kosulina, Khim. Geterotsikl. Soedin., 953 (1984). [Chem. Heterocycl. Comp., 20, 776 (1984)].
E. V. Gromachevskaya, V. G. Kul’nevich, D. P. El’chinov, T. P. Kosulina, and A. L. Chekhun, Khim. Geterotsikl. Soedin., 547 (1993). [Chem. Heterocycl. Comp., 29, 469 (1993)].
E. V. Gromachevskaya, V. G. Kul'nevich, T. P. Kosulina, T. M. Kolesnikova, A. S. Saratikov, and N. S. Livshits, USSR Inventor’s Sertificate 1279214; Byul. Izobr., No. 47, 289 (1986).
E. V. Gromachevskaya, N. I. Nen’ko, V. G. Kul’nevich, and V. P. Smolyakov, RF Pat. 2206566; Byul. Izobr., No. 17, 680 (2003).
E. V. Gromachevskaya, T. P. Kosulina, A. A. Borodavko, L. I. Isakova, and V. D. Strelkov, RF Pat. 2316209; Byul. Izobr., No. 4, 409 (2008).
E. V. Gromachevskaya, T. P. Kosulina, A. A. Borodavko, L. I. Isakova, and V. D. Strelkov, RF Pat. 2316210; Byul. Izobr., No. 4, 410 (2008).
E. V. Gromachevskaya, T. P. Kosulina, A. A. Borodavko, L. I. Isakova, and V. D. Strelkov, RF Pat. 2316211; Byul. Izobr., No. 4, 410 (2008).
E. V. Gromachevskaya, A. V. Butin, A. S. Pilipenko, G. D. Krapivin, A. Borodavko, L. I. Isakova, and V. D. Strelkov, RF Pat. 2345083; Byul. Izobr., No. 3, 1222 (2009).
V. V. Ishcheko, T. S. Shulyak, and V. N. Khilya, Khim. Geterotsikl. Soedin., 306 (2002). [Chem. Heterocycl. Comp., 38, 274 (2002)].
S. A. Glover, K. M. Jones, I. R. McNee, and C. A. Rowbottom, J. Chem. Soc., Perkin Trans. 2, 1367 (1996).
C. Paal and O. Commerell, Ber. Dtsch. Chem. Ges., 27, 1866 (1894).
C. Paal and O. Commerell, Ber. Dtsch. Chem. Ges., 27, 2427 (1894).
A. R. Ossman, H. M. Safwat, and M. A. Aziza, Indian J. Chem., B24, 333 (1985).
R. R. Schmidt and B. Beitzke, Chem. Ber., 116, 2115 (1983).
R. Lakhan and R. L. Singh, J. Prakt. Chem., 330, 299 (1988).
E. V. Gromachevskaya, T. P. Kosulina, V. G. Kul’nevich, Yu. Yu. Samitov, A. I. Khayarov, and V. T. Dubonosov, Khim. Geterotsikl. Soedin., 101 (1990). [Chem. Heterocycl. Comp., 26, 86 (1990)].
E. Ya. Lukevics (editor), Progress in the Chemistry of Furan, Zinatne, Riga (1978), p. 25.
E. V. Gromachevskaya and G. D. Krapivin, Khim. Geterotsikl. Soedin., 1586 (2004). [Chem. Heterocycl. Comp., 40, 1373 (2004)].
A. D. Cross, Introduction to Practical Infrared Spectroscopy [Russian translation], Inostr. Lit., Moscow (1961), p. 91.
L. A. Kazitsina and N. B. Kupletskaya, Uses of UV, IR, NMR, and Mass Spectrometry in Organic Chemistry [in Russian], Moscow University (1979), p. 234.
H. Budzikiewicz, C. Djerassi, and D. H. Williams, Interpretation of the Mass Spectra of Organic Compounds [Russian translation], Mir, Moscow (1966).
B. Alhede, N. Gelting, and H. Preikschat, GB Pat. Appl. 2053900.
E. V. Gromachevskaya, G. D. Krapivin, V. E. Zavodnik, and V. G. Kul’nevich, Khim. Geterotsikl. Soedin., 1391 (1997). [Chem. Heterocycl. Comp., 33, 1209 (1997)].
R. Johnstone, Handbook of Mass Spectrometry for Organic Chemists [Russian translation], Mir, Moscow (1975), p. 230.
E. V. Gromachevskaya, V. G. Kul’nevich, T. P. Kosulina, and V. S. Pustovarov, Khim. Geterotsikl. Soedin., 842 (1988). [Chem. Heterocycl. Comp., 24, 692 (1988)].
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For Communication 15, see [1].
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1691-1701, November, 2011.
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Gromachevskaya, E.V., Kul’nevich, V.G. & Kosulina, T.P. Studies of benzoxazines 16*. Synthesis and reactivity of 2,4-substituted 4H-3,1-benzoxazines. Chem Heterocycl Comp 47, 1405–1414 (2012). https://doi.org/10.1007/s10593-012-0928-z
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DOI: https://doi.org/10.1007/s10593-012-0928-z