FORMATION OF 1,2,4-TRIAZOLE DERIVATIVES BY OXIDATION OF 4-PHENYL-1-PIVALOYLSEMICARBAZIDE

Authors

  • Борис А. Гостевский A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
  • Александр И. Албанов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
  • Александр В. Ващенко A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
  • Наталья Ф. Лазарева A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

DOI:

https://doi.org/10.1007/5454

Keywords:

4-phenyl-1-pivaloylsemicarbazide, 1, 2, 4-triazol-3-one, 4-triazolidine-3, 5-dione, C, N-migration of tert-butyl group, cyclization, oxidation, structural isomers

Abstract

Oxidation of 4-phenyl-1-pivaloylsemicarbazide leads to the formation of two structural isomers: 5-tert-butyl-5-hydroxy-4-phenyl-4,5-dihydro-3H-1,2,4-triazol-3-one and 1-tert-butyl-4-phenyl-1,2,4-triazolidine-3,5-dione. Isomerization of 5-tert-butyl-5-hydroxy-4-phenyl-4,5-dihydro-3H-1,2,4-triazol-3-one to 1-tert-butyl-4-phenyl-1,2,4-triazolidine-3,5-dione proceeds upon heating and is accompanied by the migration of the tert-butyl group from the carbon atom to the nitrogen atom.

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Published

2020-09-17

Issue

Vol. 56 No. 8 (2020)

Section

Original Papers