Synthesis of beta-aminovinyl ketones of the adamantane series

1-(1-Adamantyl)-4-amino-3-buten-2-ones were synthesized by reaction of sodi um 4-(1-adamantyl)-3-oxo-1-buten-1 -olate with amine hydrochlorides. Sodium 3-R-3-oxo-1-propen-1-olates (R = methyl, phenyl, 4-chlorophenyl, 2-thienyl ) reacted with 1-adamantylamine: hydrochloride to afford 1-substituted 3-(1 -adamantylamino)-2-propen- 1-ones. Reactions of 1-adamantylamine with beta -dicarbonyl compounds (acetylacetone and ethyl acetoaoctate) in dry benzene gave 4-(1-adamantylamino)-3-penten-2-one and ethyl 3-(1-adamantylamino)-2- butenoate, respectively.