Synthesis of Adamantyl Amidoalkyl Agents and Nitrogen Heterocycles on Their Basis

Methods have been developed for the synthesis of adamantyl-containing amidoalkylating reagents: adamantyl-1-carboxy-N-(1-hydroxy-2,2,2-trichloroethyl)amide, adamantyl-1-carboxy-N-(1-chloro-2,2,2-trichloroethyl)amide, adamantyl-1-carboxy-N-(2,2,2-trichloroethylidene)amide, adamantyl-1-carboxy-N-(2,2-dichloro-1cyanovinyl)amide, 2-(adamantyl-1-carboxamido)-3,3-dichloroacrylamide, and 2-(adamantyl-1-carboxamido) 3,3-dichloroacrylic acid. Using these reagents, 2-(adamantan-1-yl)-4-(dichloromethylene)oxazol-5(4H)-one and 2-(adamantan-1-yl)-4-(dichloromethylene)-1H-imidazol-5(4H)-one were obtained via cyclocondensations in 73% and 76% yields, respectively. All products were identified by IR and 1H NMR spectra.