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Synthesis of some optically active terpenoid-derived thioamides

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journal contribution
posted on 2016-02-06, 21:42 authored by Tadeusz S. Jagodziński, Jacek G. Sośnicki, Łukasz Struk

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.

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