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Synthesis 1989; 1989(12): 923-929
DOI: 10.1055/s-1989-27431
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Synthesis of 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives from Methyl 2-Methyldithiocarbazate and Heterocumulenes

Pedro Molina* , Alberto Tárraga, Arturo Espinosa
  • *Departamento de Química Orgánica, Facultad de Ciencias Químicas y Matemáticas, Universidad de Murcia, Campus de Espinardo, E-30071 Murcia, Spain
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Publikationsdatum:
02. Mai 2002 (online)

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Methyl 2-methyldithiocarbazate 1, reacts with diarylcarbodiimides to give 4-aryl-3-arylamino-1-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazoles 3. Compound 1 also reacts with isothiocyanates to give the corresponding 5-arylamino-3-methyl-2-thioxo-2,3-dihydro-1,3,4-thiadiazoles 6. The reaction of the 3-triphenylphosphoranylidene derivative of 1 with aromatic isocyanates leads to the mesoionic anhydro-2-arylamino-4-methyl-5 -methylthio-1,3,4-thiadiazolium hydroxides 10. Methyl 3-aminocarbonyl-2 -methyldithiocarbazates 11, available from 1 and isocyanates, undergo ring closure on reaction with thionyl chloride to give either 1,3,4-thiadiazole derivatives 12 or 1,2,4-triazole derivatives 13.