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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 11
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Original Articles

Synthesis of 6-Hydroxy-2-methyl-3-thioxo-2H-1,2,4-triazin-5-one

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Pages 2075-2084 | Received 25 Sep 1995, Published online: 21 Aug 2006

References and Notes

  • Brogden , R. N. and Ward , A. 1988 . Drugs , 35 : 604
  • Stoeckel , K. 1981 . Chemotherapy , 27 ( Suppl. 1 ) : 42
  • Milner , P. H. , Guest , A. W. , Harrington , F. P. , Ponsford , R. J. , Smale , T. C. and Stachulski , A. V. 1984 . J. Chem. Soc., Chem. Commun , : 1335
  • Hoffman-La Roche , F. Brit. Patent, 1,471,804 .
  • Reiner , R. , Weiss , U. , Brombacher , U. , Lanz , P. , Montavan , M. , Furlenmeier , A. , Angehrn , P. and Probst , P. J. 1980 . J. Antibiot. , 33 : 783
  • Pesson , M. and Antoine , M. 1970 . Bull. Soc. Chim. France , 4 : 1590
  • Pesson , M. and Antoine , M. 1970 . Bull. Soc. Chim. France , 4 : 1599
  • Stefanic , A. , Valencic , M. , Tisler , V. , Kobal , E. , Vitezic , N. and Japelj , M. 1990 . Vestn. Solv. Kem. Drugs , 37 : 189
  • Neunhoeffer , M. and Wiley , P. F. 1978 . Heterocyclic Compounds Vol. 33, Chemistry of 1,2,3-Triazines, 1,2,4-Triazines and Pentazines , John Wiley and Sons .
  • Greer , A. H. and Smith , B. G.L. 1950 . J. Amer. Chem. Soc. , 72 : 874
  • Jensen , K. A. , Anthoni , U. , Kagi , B. , Larsen , C. and Pederson , C. T. 1968 . Acta. Chem. Scand. , 22 : 1
  • Although acylation of 1,2,4-trimethylthiosemicarbazide (A) with ethyl oxalyl chloride is reported7 to occur at N-(1), the authors did not exclude reaction at the alternative N(4). Interestingly, the thus formed oxalamide (B) could not be cyclised to the trimethyl-1,2,4-triazine (C) Attempted direct conversion of (A) into (C) (diethyl oxalate/sodium ethoxide) was also unsuccessful.7
  • Levy , G. C. and Lichter , R. L. 1979 . Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy , John Wiley and Sons . The expected α -shift of a nitrogen following replacement of a proton by -COCO2R is in the range of 40–80 ppm, see
  • Branch , C. L. , Basker , M. J. , Finch , S. C. , Guest , A. W. , Harrington , F. P. , Kaura , A. C. , Knott , S. J. , Milner , P. H. and Pearson , M. J. 1987 . J. Antibiot. , 40 : 646
  • These differences (260°C4 and 235–240°C8) in melting “point” may be the result of different protomeric forms of the same compound in the solid arising from differing experimental procedures employed during crystallisation.
  • Valencic , M. , Golic , L. , Japelj , M. and Stefanic , A. 1993 . Acta Cryst. , C49 : 241
  • Atomic coordinates, bond lengths and angles and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK. Tables of structure factors may be obtained through request to DSE.

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