Abstract

Deprotonation of N-ethylidene-tert-butylamine with lithium diisopropylamide and subsequent condensation with Et trifluoroacetate gives 4-tert-butylamino-1,1,1-trifluorobut-3-en-2-one. An exchange of the amino substituent occurs when the latter compd. is treated with anilines under mildly acidic conditions. When heated in the presence of phosphoryl trichloride, the resulting 4-anilino-1,1,1-trifluorobut-3-en-2-ones undergo an N -> ortho shift of the side chain followed by cyclization and dehydration to afford 2-(trifluoromethyl)quinolines. [on SciFinder (R)]

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