Synthesis of fluorinated hexahydroquinolines, bis acridinediones, xanthenediones and tetrahydro chromene carboxylates as potential drug candidates
Fluorine-containing building blocks are useful for the preparation of fluorinated pharmaceuticals and agrochemicals. Many of the existing procedures for the preparation employ solvents or reagents that are hazardous. In addition, commercially available fluorine building blocks are expensive. 5-Trifluoromethyl-1, 3-cyclohexanedione (1) was developed by our group as a versatile trifluoromethyl building block. Its reaction with a wide range of substituted aldehydes in a one-pot multicomponent method was studied. Several fluorinated hexahydroquinolines were prepared by reacting 5-trifluoromethyl-1, 3-cyclohexanedione with substituted aromatic aldehydes, beta-ketoesters, and ammonium acetate in trifluoroethanol. Two Bis-trifluoromethyl acridinediones (5) were prepared by reacting two equivalents of 5- Trifluoromethyl-1, 3-cyclohexanedione ( 1), substituted aromatic aldehydes and ammonium acetate. Ten Bis-trifluoromethylated xanthenediones (3) were prepared from two equivalents of 5- Trifluoromethyl-1, 3-cyclohexanedione (1 ) and substituted aromatic aldehydes in HCl-saturated ethanol under microwave irradiation. Eight Tetrahydrochromene carboxylate (6) were prepared from one equivalent of cyclic 1, 3-dicarbonyl (two of which included 5- Trifluoromethyl-1, 3-cyclohexanedione (1) and acetylenedicarboxylate in triethylamine containing dichloromethane at room temperature. All compounds synthesized were characterized by NMR, GC-MS and elemental analysis and will be submitted for in vitro cytotoxicity testing.
Mumiye A Ogunwale,
"Synthesis of fluorinated hexahydroquinolines, bis acridinediones, xanthenediones and tetrahydro chromene carboxylates as potential drug candidates"
ETD Collection for Tennessee State University.