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.

BUSCEMI S, PACE A, PALUMBO PICCIONELLO A, MACALUSO G, VIVONA N, SPINELLI D, et al. (2005). 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. JOURNAL OF ORGANIC CHEMISTRY, 70(8), 3288-3291 [10.1021/jo047766s].

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

BUSCEMI, Silvestre;PACE, Andrea;PALUMBO PICCIONELLO, Antonio;MACALUSO, Gabriella;VIVONA, Nicolo';
2005

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.
Settore CHIM/06 - Chimica Organica
BUSCEMI S, PACE A, PALUMBO PICCIONELLO A, MACALUSO G, VIVONA N, SPINELLI D, et al. (2005). 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. JOURNAL OF ORGANIC CHEMISTRY, 70(8), 3288-3291 [10.1021/jo047766s].
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10447/27948
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