REACTIONS OF β-ALKOXYVINYL TRIFLUOROMETHYL KETONES. THE SYNTHESIS OF N-[1-ARYL-3-OXO-4,4,4-TRIFLUORO-1-BUTEN-1-YL]-o-PHENYLENEDIAMINES AND 4-ARYL-2-TRIFLUOROMETHYL-3H-1,5-BENZODIAZEPINES

ABSTRACT

A series of five N-[1-aryl-3-oxo-4,4,4-trifluoro-1-buten-1-yl]-o-phenylenediamines 2 [CF₃COCH=C(R)NH-o-PhNH₂], where R=Ph, 4-MePh, 4-BrPh, 4-ClPh, 4-OMePh from the reaction of β-aryl-β-methoxyvinyl trifluoromethyl ketones 1 with o-phenylenediamine was prepared and isolated in good yield (59–71%). Another series of five 4-aryl-2-trifluoromethyl-3H-1,5-benzodiazepines 3, where aryl=Ph, 4-MePh, 4-BrPh, 4-ClPh, 4-OMePh was also obtained in an one-step reaction from ketones 1 by an intramolecular cyclization reaction with o-phenylenediamine under mild acid conditions in good yields (60–77%).

ACKNOWLEDGMENTS

The authors thank the financial support from the Conselho Nacional de Desenvolvimento Científico de Tecnológico (CNPq/PADCT III-Proj. 62.0228/97-0-QEQ).