4.1 Article

2-Polyfluoroalkylchromones - 8. 2-Trifluoromethyl- and 6-vitro-2-trifluoromethylchromones in reactions with amines

Journal

RUSSIAN CHEMICAL BULLETIN
Volume 50, Issue 8, Pages 1426-1429

Publisher

CONSULTANTS BUREAU
DOI: 10.1023/A:1012741224882

Keywords

2-trifluoromethylchromones; primary and secondary amines; beta-amino-beta-trifluoromethyl vinyl ketones; 2,3-dihydro-1H-1,4-diazepine derivatives; 2-morpholino- and 2-piperidino-2-trifluoromethylchroman-4-ones

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The reactions of 6-vitro-2-trifluoromethylchromone with benzylamine, ethanolamine, and aniline afforded 3-benzyl(2-hydroxyethyl,phenyl)amino-4,4,4-trifluoro-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-ones, respectively, whereas the reactions with ethylenediamine and diethylenetriamine gave rise to 5-(2-hydroxy-5-nitrophenyl)-7-trifluoromethyl-2,3-dihydro-1H-1,4-diazepine and 5-(2-hydroxy-5-nitrophenyl)-7-trifluoromethyl-1,4,8-triazabicyclo[5.3,0]dec-4-ene, respectively. Morpholine added at the double bond of 2-trifluoromethyl- and 6-nitro-2-trifluoromethylchromones to form 2-morpholino-2-trifluoromethylchroman-4-one and its 6-nitro-substituted analog, respectively, whereas piperidine reacted only with 2-trifluoromethylchromone to yield 2-piperidino-2-trifluoromethylchroman-4-one.

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