Nitrogen versus sulfur acylation in sugar thioureas: regioselectivity and conformational consequences |
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| Institution: | 1. Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Universidad de Sevilla, E-41071 Sevilla, Spain;2. Instituto de Investigaciones Quı́micas, CSIC, Américo Vespucio s/n, Isla de la Cartuja, E-41092 Sevilla, Spain;1. Infectious Diseases Therapeutic Research Center, Korea Research Institute of Chemical Technology, 141 Gajeongro, Yuseong, Daejeon 34114, Republic of Korea;2. Department of Medicinal Chemistry and Pharmacology, University of Science and Technology, 217 Gajeongro, Yuseong, Daejeon 34113, Republic of Korea |
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| Abstract: | The influence of steric and electronic effects in the regioselectivity of base-catalysed acetylation reactions of sugar thioureas and the structural and conformational properties of the resulting products have been investigated. Bulky alkyl substituents favoured S-acetylation, whereas aryl substituents directed acylation at nitrogen. The conformational properties of both the S- and N-acetyl compounds are governed by the existence of a strong six-membered NH···OC intramolecular hydrogen bond that locks the pseudoamide bonds in a rigid configurational arrangement. |
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