Reactions of 2-Chlorocycloalkanone Oximes. II. Syntheses of 3-Aminocycloalka[C]isoxazoles

The displacement reactions of α-chlorocycloalkanone oximes with sodium cyanide in dimethyl sulfoxide or ethanol have been studied. It has been shown that 3-aminocycloalka[C]-isoxazoles can be obtained in excellent yields. α-Chlorooximes of cyclohexanone, cyclooctanone, cycloocten-5-one, cyclododecanone, and cyclododecadien-5, 9-one have been subjected to the reaction, affording the corresponding isoxazole derivatives in 48, 96, 89, 95, and 90% yields respectively. The application of the method to 3-chloronorcamphor oxime and α-chlorooximes from acyclic olefins afforded cyanooximes; it failed to give isoxazole derivatives. The hydrogenation of 3-aminocycloocta[C] isoxazole gave 2-amino-1-cyclooctanecarbonamide by the hydrogenolysis of the nitrogen-oxygen bond of the isoxazole ring system. The amino-carbonamide was treated with either the base or acid to give 2-oxycyclooctanecarboxylic acid.