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Original Articles

Synthesis of some optically active terpenoid-derived thioamides

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Pages 290-296 | Received 29 May 2015, Accepted 22 Jun 2015, Published online: 06 Feb 2016
 

GRAPHICAL ABSTRACT

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.

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