Heterocyclizations 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)oxiranes

Add time:08/21/2019    Source:sciencedirect.com

2-Aryl-3-arylamino-4,4,4-trifluoro-2-butenenitriles 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 25%–40% yield of 4-N-methylamino-3H-pyrazole-3-spiro-2′-(3′-aryl-3′-trifluoromethyl)oxiranes. However, the related reaction with diazoethane yielded only aryl(arylhydrazono)acetonitriles and other fragmentation products.

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