PDF herunterladen
Synthesis 2010(15): 2588-2598  
DOI: 10.1055/s-0029-1218840
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Synthesis of Annulated Thiatriazine Dioxides

Alexander N. Khodachenkoa,b, Alexander N. Shivanyuk*a,c, Svetlana V. Shishkinad, Oleg V. Shishkind, Konstantin G. Nazarenkoe, Andrey A. Tolmacheva,f
a ChemBioCenter, Taras Shevchenko Kiev National University, 62 Volodymyrska St., Kiev 01033, Ukraine
b Taras Shevchenko Chernigiv State Pedagogical University, 53 Getman Polubotok St., Chernigiv 14013, Ukraine
c The Institute of High Technologies, Taras Shevchenko Kiev National University, 62 Volodymyrska St., Kiev 01033, Ukraine
d STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, 60 Lenina Ave., Kharkiv 61001, Ukraine
e Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kiev 02094, Ukraine
f Enamine Ltd., 23 Alexander Matrosov St., Kiev 01103, Ukraine
Fax: +380(44)5373253; e-Mail: shivan1@yandex.ru;
Weitere Informationen

Publikationsverlauf

Received 1 March 2010
Publikationsdatum:
25. Juni 2010 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

The reactions of five-, six-, seven-, and eight-membered cyclic imido ethers with one equivalent of sulfamide lead to the corresponding sulfamoylamidines in 70-80% yields. Sulfamoyl­amidines undergo condensations with aliphatic and aromatic aldehydes as well as aliphatic ketones to give thiatriazine dioxides in 50-95% yields. The NMR spectroscopic studies reveal ring-chain tautomerism of some thiatriazine dioxides in solution. The ratio between the tautomers depends on the temperature, solvent polarity, and electronic properties of the substituents of the pendant aryl rings. Thiatriazine dioxides are readily alkylated and acylated at position 2.

Key words

imido ethers - sulfamide - sulfamoylamidines - thiatria­zine dioxides - tautomerism

    References

  • 1 Takeuchi E, Muragata M, and Takahashi S. inventors; JP  61,044,818.  ; Chem. Abstr. 1986, 105, 30069
  • 2a Ross BC, Allen RM, and Cousins SJ. inventors; EP  156,286.  ; Chem. Abstr. 1986, 104, 95470
  • 2b Ross BC, Michael JD, and Cousins SJ. inventors; EP  104,611.  ; Chem. Abstr. 1984, 101, 72766
  • 3a Hamprecht G, Parg A, and Wuerzer B. inventors; DE  3,134,145.  ; Chem. Abstr. 1983, 99, 70774
  • 3b Hamprecht G, and Wuerzer B. inventors; DE  3,231,394.  ; Chem. Abstr. 1984, 100, 209886
  • 3c Hamprecht G, Acker RD, and Wuerzer B. inventors; DE  3,016,825.  ; Chem. Abstr. 1982, 96, 69049
  • 3d Michael JD, and Ross BC. inventors; EP  170,118.  ; Chem. Abstr. 1986, 105, 42845
  • 3e Acker RD, Hamprecht G, Parg A, and Wuerzer B. inventors; DE  3,013,268.  ; Chem. Abstr. 1982, 96, 85598
  • 3f Sanemitsu M, Shiroshita M, Nakayama Y, Mizutani M, Hashimoto S, and Takase M. inventors; JP  58,219,171.  ; Chem. Abstr. 1984, 100, 191912
  • 3g Hamprecht G, Acker RD, and Wuerzer B. inventors; DE  3,134,141.  ; Chem. Abstr. 1983, 98, 198287
  • 3h Hamprecht G, Acker RD, Sauter H, Theobald H, and Wuerzer B. inventors; DE  3,143,381.  ; Chem. Abstr. 1983, 99, 53796
  • 4 Kuhla DE, Campbell HF, Studt WL, Dodson SA, Galemmo RA, and Durham PJ. inventors; WO  85,05,105.  ; Chem. Abstr. 1986, 105, 191140
  • 5 Gazieva GA. Kravchenko AN. Lebedev OV. Russ. Chem. Rev. (Engl. Transl.)  2000,  69:  239 
    Suche in Google Scholar
  • 6 Denny GH. Cragoe EJ. J. Org. Chem.  1980,  45:  1662 
    CrossrefSuche in Google Scholar
  • 7 Dusemund J. Arch. Pharm. (Weinheim, Ger.)  1977,  310:  435 
    CrossrefSuche in Google Scholar
  • 8 Duggan PJ. Liepa AJ. O’Dea LK. Tranberg CE. Org. Biomol. Chem.  2007,  5:  472 
    CrossrefSuche in Google Scholar
  • 9a Cousins SJ. Ross BC. Maw JN. Michael JD. Tetrahedron Lett.  1985,  26:  1105 
    Suche in Google Scholar
  • 9b Nakayama Y. Sanemitsu Y. J. Heterocycl. Chem.  1984,  21:  1553 
    Suche in Google Scholar
  • 10a Manfred H. Bernd S. Synthesis  1991,  753 
  • 10b Durham PJ. Galemmo RA. Tetrahedron Lett.  1986,  27:  123 
    Suche in Google Scholar
  • 10c Michael JD. Rees PM. Ross BC. Tetrahedron Lett.  1985,  26:  1101 
    Suche in Google Scholar
  • 10d Hamprecht G. Acker R.-D. Hadicke E. Liebigs Ann. Chem.  1985,  2363 
  • 10e Michael JD. Synthesis  1987,  170 
  • 10f Nakayama Y. Sanemitsu Y. Synthesis  1984,  773 
  • 10g Knollmuller M. Kosma P. Monatsh. Chem.  1981,  112:  489 
    Suche in Google Scholar
  • 11 Schmidt KF, and Zutavern P. inventors; DE  532,969.  ; Friedländer 1931, 18, 3050
  • 12 Burgi H.-B. Dunitz JD. Structure Correlation   Vol. 2:  VCH; Weinheim: 1994.  p.741 
    Suche in Google Scholar
  • 13 Ro S. Rowan SJ. Pease AR. Cram DJ. Stoddart JF. Org. Lett.  2000,  2:  2411 
    CrossrefSuche in Google Scholar
  • 14 Sheldrick GM. Acta Crystallogr., Sect. A  2008,  64:  112 
    CrossrefPubMedSuche in Google Scholar