Synthesis of N‐,O‐,S‐Heterocyclic Spiroadamantanes by Condensation of Ketones with Bifunctional OH‐, NH‐, SH‐Acids under the Action of Copper‐Containing Catalysts

Abstract

Synthesis of adamantyl‐containing cyclic ketals, spirooxazolidines, spiroimidazolidines, spirooxathiolanes, spirodithiolanes, spirooxazines, spirobenzodioxoles with high yields was carried out by condensation of adamantyl‐containing ketones (adamantanone, kemantan, diamantanone) with diols, 1,2‐ethanedithiol and 2‐mercaptoethanol, 1,2‐diaminoethane and 2‐aminoethanol under the action of copper‐containing catalysts. In the case of multigram‐scale reaction of adamant‐2‐one with 1,2‐propanediol, the amount of catalyst can be reduced to 0.1 mol %.