Independently of the reaction conditions N-allylisatin forms only the 2,3-dibromo derivative upon treatment with molecular bromine in contrast to N-allyl-substituted quinolin- or pyrid-2-ones which readily undergo halocyclization to the corresponding 2-bromomethyl oxazoles.
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I. V. Ukrainets, Liu Yangyang, N. L. Bereznyakova, and A. V. Turov, Khim. Geterotsikl. Soedin., 1539 (2009). [Chem. Heterocycl. Comp., 45, 1236 (2009)].
F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry. Pt. B: Reactions and Synthesis, 5th ed., Springer USA (2007), p. 310. Online version available.
J. W. Chern, C. Y. Shiau, and G. Y. Lu, Bioorg. Med. Chem. Lett., 1, 571 (1991).
M. D'hooghe, J. Baele, J. Contreras, M. Boelens, and N. De Kimpe, Tetrahedron Lett., 49, 6039 (2008).
T. Hu, M. Shen, Q. Chen, and C. Li, Org. Lett., 8, 2647 (2006).
T. M. Ugurchieva, A. V. Lozanova, M. V. Zlokazov, and V. V. Veselovsky, Russian Chem. Bull., Int. Ed., 56, 1544 (2007).
V. N. Britsun, A. N. Esipenko, V. I. Staninets, and M. O. Lozinskii, Khim. Geterotsikl. Soedin., 1114 (2005). [Chem. Heterocycl. Comp., 41, 948 (2005)].
I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, S. V. Shishkina, and A. V. Turov, Khim. Geterotsikl. Soedin., 736 (2007). [Chem. Heterocycl. Comp., 43, 617 (2007)].
I. V. Ukrainets, N. L. Bereznyakova, O. V. Gorokhova, A. V. Turov, ad S. V. Shishkin, Khim. Geterotsikl. Soedin., 1180 (2007). [Chem. Heterocycl. Comp., 43, 1001 (2007)].
I. V. Ukrainets, N. L. Bereznyakova, V. A. Parshikov, and A. V. Turov, Khim. Geterotsikl. Soedin., 1496 (2007). [Chem. Heterocycl. Comp., 43, 1296 (2007)].
G. I. Zhungietu and M. A. Rekhter, Isatin and its Derivatives [in Russian], Shtiintsa, Kishinev (1977), p. 33.
H.-B. Burgi and J. D. Dunitz, Structure Сorrelation, Vol. 2, VCH, Weinheim (1994), p. 741.
M. H. Palmer, A. J. Blake, and R. O. Gould, Chem. Phys., 115, 219 (1987).
J. Zukerman-Schpector, E. E. Castellano, A. D. C. Pinto, J. F. M. da Silva, and M. T. F. C. Barcellos, Acta Crystallogr., C48, 760 (1992).
J. Zukerman-Schpector, A. D. C. Pinto, J. F. M. da Silva, and M. T. F. C. Barcellos, Acta Crystallogr., C51, 675 (1995).
G. Miehe, P. Susse, V. Kupcik, E. Egert, M. Nieger, G. Kunz, R. Gerke, B. Knieriem, M. Niemeyer, and W. Luttke, Angew. Chem., Int. Ed., 30, 964 (1991).
Yu. V. Zefirov, Kristallografiya, 42, 936 (1997).
S. M. Khripak, M. V. Slivka, R. V. Vilkov, R. N. Usenko, and V. G. Lendel, Khim. Geterotsikl. Soedin., 922 (2007). [Chem. Heterocycl. Comp., 43, 781 (2007)].
M. V. Slivka, Dis. Cand. Chem. Sci. [in Russian], Kiev (2001).
M. V. Slivka, S. M. Khripak, V. N. Britsun, and V. I. Staninets, Zh. Org. Khim., 36, 1064 (2000).
D. G. Kim, V. V. Avdin, and L. V. Garrilova, Khim. Geterotsikl. Soedin., 1130 (1997). [Chem. Heterocycl. Comp., 33, 986 (1997)].
D. G. Kim, Khim. Geterotsikl. Soedin., 566 (1998). [Chem. Heterocycl. Comp., 34, 505 (1998).
Y. G. Kim and J. K. Cha, Tetrahedron Lett., 30, 5721 (1989).
L. A. Paquette, G. D. Crouse, and A. K. Sharma, J. Am. Chem. Soc., 102, 3972 (1980).
I. V. Ukrainets, N. L. Bereznyakova, V. A. Parshikov, and A. V. Turov, Khim. Geterotsikl. Soedin., 1496 (2007). [Chem. Heterocycl. Comp., 43, 1269 (2007)].
A. F. Pozharskii, Theoretical Basis for the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985), p. 158.
I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, N. L. Bereznyakova, and S. V. Shishkina, Khim. Geterotsikl. Soedin., 1502 (2006). [Chem. Heterocycl. Comp., 42, 1296 (2006)].
G. M. Sheldrick, SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data. Rev. 5.1 (1998).
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For Communication 169 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1546-1553, October, 2009.
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Ukrainets, I.V., Bereznyakova, N.L., Gorokhova, O.V. et al. 4-hydroxy-2-quinolones 170*. synthesis and bromination of N-allylisatin. Chem Heterocycl Comp 45, 1241–1247 (2009). https://doi.org/10.1007/s10593-010-0413-5
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DOI: https://doi.org/10.1007/s10593-010-0413-5