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4-Phenyl-1,2,4-triazole-3,5-dione

4-Phenyl-1,2,4-triazole-3,5-dione

4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) is an azodicarbonyl compound. PTAD is one of the strongest dienophiles and reacts rapidly with dienes in Diels-Alder reactions. The most prominent use of PTAD was the first synthesis of prismane in 1973.

Synthesis

The compound was first synthesized in 1894 by Johannes Thiele and . The oxidation of 4-Phenylurazole with lead tetroxide in sulfuric acid yielded small quantities of the substance. It took until 1971 until a practical synthesis was published. The synthesis starts by combining hydrazine and diethyl carbonate. The product of this step is reacted with phenyl isocyanate to form 4-Phenyl-1-carbethoxysemicarbazide (4), which is cyclized with base to form 4-Phenylurazole (5). Oxidation with tert-Butyl hypochlorite then yields PTAD (6).

Synthesis of PTAD

References

References

  1. (1983). "4-Phenyl-1,2,4-triazoline-3,5-dione in organic synthesis (review)". Chemistry of Heterocyclic Compounds.
  2. Katz T. J., Acton N.. (1973). "Synthesis of Prismane". [[Journal of the American Chemical Society]].
  3. (1894). "Ueber Semicarbazid". Justus Liebigs Annalen der Chemie.
  4. Cookson, R. C.. (1971). "4-Phenyl-1,2,4-triazole-3,5-dione". Organic Syntheses.
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triazoles phenyl-compounds
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