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FORMATION OF 1,2,4-TRIAZOLE DERIVATIVES BY OXIDATION OF 4-PHENYL-1-PIVALOYLSEMICARBAZIDE
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.
Keywords
4-phenyl-1-pivaloylsemicarbazide, 1,2,4-triazol-3-one, 1,2,4-triazolidine-3,5-dione, C,N-migration of tert-butyl group, cyclization, oxidation, structural isomers
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Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv