ABSTRACT
Several terpenoid-derived thioamides have been synthesized in the reactions taking advantage of the electrophilicity of the carbonyl function in terpenones and the nucleophilicity of the terpenone lithium enolates. The optically active β-hydroxythioamide derivatives 4, 6, 8, 10, 12 have been obtained by reacting the thioacetanilide dianion 2 with terpenones. The reaction of the enolate anions of (-)-menthone and (1R)-(+)-camphor with phenyl isothiocyanate gave rise to the formation of the corresponding β-ketothioamides 13, 14. In a multicomponent reaction (MCRs) with benzylamine and formaldehyde, 14 yielded the spirohexahydropyrimidine 15.
Acknowledgments
We express our thanks to Professor Jerzy Lange of the Warsaw University of Technology for helpful discussions and assistance with the manuscript.