88579-71-9Relevant academic research and scientific papers
Unsaturated nitrogen compounds containing fluorine. Part 16. The synthesis of 3,5-bis(trifluoromethyl)-1H-1,2,4- triazole and some 4-substituted derivatives from 2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene
Abdul-Ghani, Mohammad M.,Tipping, Anthony E.
, p. 95 - 106 (2007/10/02)
The dichloroazine 5 has been converted into the monoaminoazines CF3C(NHR)=NN=CClCF3 (6) and the diaminoazines CF3C(NHR)=NN=C(NHR)CF3 (4) by reaction with ammonia or the appropriate primary amino compound; with hydroxylamine the syn-oxime CF3CCl=NNHC(CF3)=NOH (8) (86percent) was formed.The mixed diaminoazines CF3C(NHR)=NN=C(NHR')CF3 (4) have been synthesised from the monoaminoazines 6a-d.A solution of the diaminoazine 4c, heated in ethanol under reflux, gave 3,5-bis(trifluoromethyl)-1H-1,2,4-triazole (1a) (28percent) and its ammonium salt NH4+- (7b) (54percent), while the azines 4g and 4j under the same conditions each afforded 4-phenyl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazole (2c) (ca. 85percent).Thermolysis of the diaminoazines 4c-f and 4h in vacuo over the range 120-150 deg C gave the following results: 4c--->7b (98percent); 4d--->MeNH3+- (7c) (ca. 26percent) + Me4N+- (7d) (ca.13percent) + 4-methyl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazole (2b) (54percent) + 1-methyl-3,5-bis(trifluoromethyl)-1H-1,2,4-triazole (1b) (1.5percent); 4e---> the 4-carbomethoxymethyltriazole (2e) (93percent); 4f---> the 4-carboethoxymethyltriazole (2f) (82percent); 4h--->1a (11percent) + 2b (54percent) + 7c (31percent).Treatment of salt 7b with aqueous hydrochloric acid afforded the triazole 1a (75percent). - Keywords: Unsaturated nitrogen compounds; Synthesis; Bis(trifluoromethyl)triazole; NMR spectroscopy; Mass spectrometry
Unsaturated nitrogen compounds containing fluorine. Part 9. The preparation of 2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene and its reaction with amines
Bell, David,Eltoum, Ahmed O. A.,O'Reilly, Neil J.,Tipping, Anthony E.
, p. 151 - 166 (2007/10/02)
2,5-Dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene (1) has been prepared in good yield (60percent) by the reaction of 1,2-bis(trifluoroacetyl)hydrazine with a mixture of N,N-dimethylaniline hydrochloride and phosphoryl chloride.Nucleophilic displ
Reaction of 2,5-Bis(trifluoromethyl)-1,3,4-oxadiazole with Primary Amines. Synthesis of 4-Substituted-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles
Reitz, David B.,Finkes, Michael J.
, p. 225 - 230 (2007/10/02)
Reaction of 3,5-bis(trifluoromethyl)-1,3,4-oxadiazole (1a) with primary amines under a variety of conditions conveniently produced 4-substituted-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles 4a in 26-85percent yield.Alkyl amines reacted with 1a in methanol
The Preparation and Some Reactions of 2,5-Dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene
Barlow, Michael G.,Bell, David,O'Reilly, Neil J.,Tipping, Anthony E.
, p. 293 - 300 (2007/10/02)
The title azine(I) can be conveniently prepared by treatment of 1,2-bistrifluoroacetylhydrazine with NN-dimethylaniline hydrochloride in phosphoryl chloride at ca. 100 deg C.It undergoes facile displacement of one or both chlorine atoms on treatment with a variety of nitrogen-, oxygen- and sulphur-centred nucleophiles as well as with iodide and fluoride ions.The bisanilino-substituted azine (Vd) is thermally unstable and cyclises with elimination of aniline to the triazole (VIa), while the perfluoroazine (Vj) undergoes cycloaddition with acetylene.
