- Heterocyclization of 2-aryl-3-arylamino-4,4,4-trifluoro-2-butenenitrile hydrates to 3-aryl-2-trifluoromethyl-4-quinolones and to 4-N-methylamino-3H-pyrazole-3-spiro-2'-(3'-aryl-3'-trifluoromethyl)axiranes
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2-Aryl-3-arylamino-4,4,4-trifluoro-2-butenitriles were obtained as hydrates from 3-oxo-2-aryl-4,4,4-trifluorobutyronitriles and anilines and their structure and heterocyclizations studied.Cyclization with polyphosphoric acid gave poor yields of 3-aryl-2-trifluoromethyl-4-quinolones, but they underwent an interesting cyclization with diazomethane to give a 25percent-40percent yield of 4-N-methylamino-3H-pyrazole-3-spiro-2'-(3'-aryl-3'-trifluoromethyl)oxiranes.However, the related reaction with diazoethane yielded anly aryl(arylhydrazono)acetonitriles and other fragmentation products. - Keywords: Heterocyclizations; Fluorinated oxiranes; NMR spectroscopy; IR spectroscopy; UV spectrophotometry
- Nishiwaki, Tarozaemon,Kikukawa, Hirofumi,Kawaji, Takatoshi
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- Aryl Halides as Convenient Precursors of Electrogenerated Bases. Efficient Syntheses of β-Oxo Nitriles or Esters by Coupling Active-hydrogen Groups with Esters
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In an undivided cell fitted with a sacrificial anode and a nickel cathode on which cadmium had been deposited, the electroreduction of aromatic halides affords a strong base which allows the effective synthesis of β-oxo nitriles or β-oxo esters from the coupling of active-hydrogen compounds with esters.
- Barhdadi, Rachid,Gal, Jacques,Heintz, Monique,Troupel, Michel
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