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Toposelective synthesis under thermodynamic control and bioactivities of topoisomers based on diethoxycarbonyl glycoluril derivatives

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Chinese Science Bulletin

Abstract

Six topoisomers consisting of diethoxycarbonyl glycoluril have been successfully synthesized in one-pot by using a “figure-of-seven” building block through anti-connectivity and syn-connectivity reactions, respectively. The structures of all six topoisomers were first determined by X-ray crystallography. The finding that (±) CT isomers are the dominant products under thermodynamic control can be explained by the calculated relative energies of the six topoisomers. That the (±) CT isomers have the lowest energy is most likely due to the additional intramolecular electrostatic interactions between-NO2 and-OMe groups. The biological activities of the topoisomers were primitively investigated and the results of bioassay showed that the six topoisomers possessed obvious difference of herbicidal activity.

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Authors and Affiliations

  1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Department of Chemistry, Central China Normal University, Wuhan, 430079, China

    Zhou Baohan, Yin Guodong, Wang Zhiguo, Chen Yunfeng, Wu Anxin & Wan Jian

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  1. Zhou Baohan
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  2. Yin Guodong
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  3. Wang Zhiguo
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  4. Chen Yunfeng
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  5. Wu Anxin
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  6. Wan Jian
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Correspondence to Wu Anxin or Wan Jian.

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Zhou, B., Yin, G., Wang, Z. et al. Toposelective synthesis under thermodynamic control and bioactivities of topoisomers based on diethoxycarbonyl glycoluril derivatives. CHINESE SCI BULL 51, 2164–2168 (2006). https://doi.org/10.1007/s11434-006-2089-x

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  • DOI: https://doi.org/10.1007/s11434-006-2089-x

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