Download PDF
Synthesis 2004(1): 17-19  
DOI: 10.1055/s-2003-44377
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

New Cyclizing Reagent for the Synthesis of 1,3,4-Thiadiazoles

Vladimir N. Yarovenko*, Aleksandr V. Shirokov, Igor V. Zavarzin, Oksana N. Krupinova, Anatolii V. Ignatenko, Mikhail M. Krayushkin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia
Fax: +7(95)135 5328; e-Mail: yarov@mail.ioc.ac.ru;
Further Information

Publication History

Received 27 August 2003
Publication Date:
17 December 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

A new cyclizing reagent is proposed for the synthesis of 5-unsubstituted 1,3,4-thiadiazoles. The latter are formed in good yields by the reactions of thiohydrazides with diethyl chlorophosphate in DMF.

Key words

oxamic thiohydrazides - diethyl chlorophosphate - phosphorus oxychloride - dimethylformamide - unsubstituted carbamoyl-1,3,4-thiadiazoles

    References

  • 1 Katrizky A. Comprehensive Heterocyclic Chemistry   Vol. 6:  Pergamon; Oxford: 1984. 
    Google Scholar
  • 2 Diamond S, and Sevrain C. inventors; PCT Int. Appl., WO  2003016870.  ; Chem. Abstr. 2003, 138, 198554
  • 3 Nakao H, Matsuzaki Y, Tohnishi M, Mmorimoto M, Fujioka S, Takemoto T, and Mamezuka K. inventors; PCT Int. Appl., WO  2002092584.  ; Chem. Abstr. 2002, 137, 384845
  • 4 Takatori Y, Yamaguchi T, and Nagakura M. inventors; Jpn Kokai Tohkyo Koko  8028946.  ; Chem. Abstr., 1980, 93, 114536
  • 5 Gadwood R, Barbachyn M, Toops D, and Vaillancourt V. inventors; US Pat.  5736545.  ; Chem. Abstr. 1998, 128, 270612
  • 6 Sulphur, Selenium and Tellurium, Specialist Periodical Reports   Vol. 2:  The Chemical Society; London: 1973. 
    Google Scholar
  • 7 Aromatic and Heteroaromatic Chemistry, Specialist Periodical Reports   Vol. 2:  The Chemical Society; London: 1974. 
    Google Scholar
  • 8 Hackbarth C. Chen D. Lewis J. Clark K. Mangold J. Cramer J. Margolis P. Wang W. Koehn J. Wu C. Lopez S. Withers G. Gu H. Dunn E. Kulathila R. Pan S. Porter W. Jacobs J. Trias J. Patel D. Weidmann B. White RJ. Yuan Z. Antimicrob. Agents Chemother.  2002,  46:  2752 
    CrossrefGoogle Scholar
  • 9 Kristen R, Mullrt K, and Jansen J. inventors; Ger Offen. DE  4233195.  ; Chem. Abstr. 1994, 120, 323579m
  • 10 Yarovenko VN. Shirokov AV. Krupinova ON. Zavarzin IV. Krayushkin MN. Zh. Org. Khim.  2003,  39:  1204 
    Google Scholar
  • 11 Treppendahl S. Jakobsen P. Acta Chem. Scand. Ser. B  1977,  31:  264 
    Google Scholar
  • 12 Thiel W. Mayer R. J. Prakt. Chem.  1989,  331:  649 
    Google Scholar