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

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.

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. 

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. 

7 Aromatic and Heteroaromatic Chemistry, Specialist Periodical Reports   Vol. 2:  The Chemical Society; London: 1974. 

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 

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 

11 Treppendahl S. Jakobsen P. Acta Chem. Scand. Ser. B  1977,  31:  264 

12 Thiel W. Mayer R. J. Prakt. Chem.  1989,  331:  649