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Synthesis 2004(8): 1195-1202  
DOI: 10.1055/s-2004-822375
PAPER
© Georg Thieme Verlag Stuttgart · New York

2-Hetaryl Derivatives of 3-Oxo-3,4-dihydro-2H-1,4-benzothiazine

Konstantin G. Nazarenko*a, Nataliya A. Shtilb, Alexander N. Chernegaa, Miron O. Lozinskiia, Andrey A. Tolmachevc
a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya 5, Kyiv-94, 02094, Ukraine
b Chernigov State University of Technology, Shevchenko 95, Chernigov, 14027, Ukraine
Fax: +38(44)5590480; e-Mail: Shnataliya@ukr.net;
c Research and Development Center for Chemistry and Biology, National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine
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Publication History

Received 12 February 2004
Publication Date:
10 May 2004 (online)

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Abstract

A new approach for the synthesis of 2-hetaryl derivatives of 3-oxo-3,4-dihydro-2H-1,4-benzothiazines is described. 2-Chloro derivatives of 2a,b were reacted with electron-rich heterocycles 3-14 under basic catalysis (with a slight excess of Et3N) to provide the substitution products 16-36. In the reaction of 2b with 14 and 15, an intermolecular cyclization took place between the amino and ethoxycarbonyl groups, resulting in spiro compounds 35 and 36, respectively.

Key words

chloro derivatives - electron-rich heterocycles - electrophilic substitution - cyclization - spiro compounds

    References

  • 1 Brown C. Davidson RM. Adv. Heterocycl. Chem.  1985,  38:  135 
    Search in Google Scholar
  • 2 Lozinskii MO. Demchenko AM. Shivanuk AF. Synthesis and Properties of Derivatives of 1,4-Benzo-thiazines, In Advanced Methods of Synthesis and Modifications of Heterocycles   Vol. 2:  Karcev VG. JBS Press; Moscow: 2003. 
    Search in Google Scholar
  • 3 Fujita M. Ito S. Ota A. Kato N. Yamamoto K. Kawashima Y. Yamauchi H. Iwao J. J. Med. Chem.  1990,  33:  1898 
    CrossrefSearch in Google Scholar
  • 4 Iwao J, Iso T, and Oya M. inventors; Jpn. Kokai Tokkyo Koho, JP  60166674.  ; Chem. Abstr. 1986, 104, 109666p
  • 5 Iwao J, Iso T, and Oya M. inventors; PCT Int. Appl., WO  8605490.  ; Chem. Abstr. 1987, 106, 18586n
  • 6 Okami Y, and Kawashima Y. inventors; Jpn. Kokai Tokkyo Koho, JP  0912576.  ; Chem. Abstr. 1997, 126, 171612a
  • 7 Kawashima Y, Ota A, Araki Y, and Shii D. inventors; Jpn. Kokai Tokkyo Koho, JP  09100418.  ; Chem. Abstr. 1997, 127, 34231g
  • 8 Jacobsen N. Kolind-Andersen H. Synthesis  1990,  911 
    Thieme Connect
  • 9 Fujita M. Ota A. Ito S. Yamamoto K. Kawashima Y. Synthesis  1988,  599 
    Thieme Connect
  • 10 Worley J. Wayne R. Cammack K. J. Org. Chem.  1975,  40:  1731 
    Search in Google Scholar
  • 11 Shivanyuk AF. Lozinskii MO. Kalinin VN. Sokolova YA. Atovmyan LO. Dyachenko OA. Zh. Org. Khim.  1990,  26:  1345 
    Search in Google Scholar
  • 12 Bobrovskii SN. Lushnikov DE. Bundel YG. Khim. Geterotsikl. Soed.  1989,  12:  1634 
    Search in Google Scholar
  • 13 Prostakov NS. Baktibaev OV. Usp. Khim.  1975,  44:  1649 
    Search in Google Scholar
  • 14 Broom AD. Shim JL. Anderson GL. J. Org. Chem.  1976,  7:  1095 
    Search in Google Scholar
  • 15 Bernier J.-L. Lefebvre A. Henichart J.-P. Haussin R. Lespagnol C. Bull. Soc. Chim. Fr.  1976,  616 
  • 16 Birkinshaw TN. Gillon DW. Harkin SA. Meakins GD. Tirel MD. J. Chem. Soc., Perkin Trans. 1  1984,  2:  147 
    Search in Google Scholar
  • 17 North ACT. Phillips DC. Mathews FS. Acta Crystallogr.  1968,  A24:  351 
    Search in Google Scholar
  • 18 Watkin DJ. Prout CK. Carruthers JR. Betteridge PW. CRYSTALS   Issue 10:  Chemical Crystallography Laboratory, University of Oxford; Oxford: 1996. 
    Search in Google Scholar
  • 19 Carruthers JR. Watkin DJ. Acta Crystallogr.  1979,  A35:  698 
    Search in Google Scholar
  • 20 Flack HD. Acta Crystallogr.  1983,  A39:  876 
    Search in Google Scholar