11-Perfluoroalkyl-Substituted 3,3-Dimethyl-11-Hydroxy-2,3,4,5,10,11-Hexahydro-1h-Dibenzo[B,E][1,4]Diaz Epin-1-Ones: Synthesis And Characterization

Novel 11-perfluoroalkyl-substituted 3,3-dimethyl-11-hydroxy-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-ones are prepared via a simple two-step approach. A treatment of 2-perfluoroalkanoylcyclohexane-1,3-diones with ethereal solution of diazomethane gives 5,5-dimethyl-3-methoxy-2-perfluoroalkanoylcyclohex-2-en-1-ones as main products and 6,6-dimethyl-3-hydroxy-3-perfluoroalkyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-ones as by-products. Then, an initial methoxy group vinylogous substitution of enol ethers by one of the o-phenylenediamine amino groups and an intramolecular cyclization leads to the title compounds in high yields.