Syntheses of 4‐(5‐oxo‐1,2,4‐triazol‐3‐yl)‐sydnones and 4‐(4‐arylamino‐5‐oxo‐1,2,4‐triazol‐3‐yl)‐sydnones from Sydnone Derivatives and Their Fragments |
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Authors: | W. F. Kuo C. Y. Lee M. Y. Yeh |
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Abstract: | 4‐(5‐oxo‐1,2,4‐triazol‐3‐yl)‐sydnones 11 and 4‐(4‐arylamino‐5‐oxo‐1,2,4‐triazol‐3‐yl)‐sydnones 13 have been obtained from a‐chloroformylarylhydrazine hydrochloride 2 . Moreover, the intermediates, including 3, 4 , 9 and 10 , in this study are synthetically informative and valuable. It is also noteworthy that three reactants, 1, 2 and sydnonecarbaldehydes, were prepared from sydnone derivatives and their fragments. The oxidative cyclizations of sydnonecarbaldehyde semicarbazones 9 and carbazones 10 with two different oxidizing agents (Cu(ClO4)2 and Fe(ClO4)3) have been extensively examined. The reaction time and the yields of cyclizations were affected by the substituents of semicarbazones 9 and carbazones 10. |
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Keywords: | α ‐Chloroformylarylhydrazine hydrochloride Hydrazine Semicarbazide Carbazide Sydnonylaldehyde semicarbazone Sydnonylaldehyde carbazone 4‐(5‐Oxo‐1,2,4‐triazol‐3‐yl)‐sydnones 4‐(4‐Arylamino‐5‐oxo‐1,2,4‐triazol‐3‐yl)‐sydnones |
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