Fluorinated heterocyclic compounds. An effective strategy for the synthesis of fluorinated Z-oximes of 3-perfluoroalkyl-6-phenyl-2H-1,2,4-triazin5-ones via a ring-enlargement reaction of 3-benzoyl-5-perfluoroalkyl-1,2,4-oxadiazoles and hydrazine

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Abstract

The reaction of 3-benzoyl-5-perfluoroalkyl-1,2,4-oxadiazoles with hydrazine has been investigated, evidencing the possibility of competitive reaction paths. Nucleophilic addition of the hydrazine to the electrophilic C(5) of the 1,2,4-oxadiazole ring, followed by ring opening and ring closure with enlargement, leads with high yield and in very mild experimental conditions to the formation of Z-oximes of 3-perfluoroalkyl-6-phenyl-2H-1,2,4-triazin-5-ones (11a-c) as major products of the reaction. In turn, the hydrazine can attack the electrophilic carbonyl carbon giving 4-perfluoroacylamino-5-phenyl-2H-1,2,3-triazoles (13a-c) through the well-known Boulton-Katritzky rearrangement of the intermediate hydrazones.
Lingua originaleEnglish
pagine (da-a)3288-3291
Numero di pagine4
RivistaJournal of Organic Chemistry
Volume70
Stato di pubblicazionePublished - 2005

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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