Preparation and reaction of uracil substituted cyclen and cyclam: formation of tricyclic guanidinium and dihydroimidazolium salts |
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Authors: | Soichiro Watanabe Ayako Komori Akira Uchida |
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Institution: | a Department of Biomolecular Science, Faculty of Science, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan b Research Center for Materials with Integrated Properties, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan |
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Abstract: | Di-uracil substituted cyclen derivatives were prepared by the reaction of cyclen with 6-chloro-1-methyluracil or 6-chloro-1,3-dimethyluracil. The reaction of cyclam with 6-chloro-1,3-dimethyluracil gave a similar di-uracil substituted cyclam. The 1,7-di-uracil substituted cyclen was converted to the tricyclic guanidinium salt and acylurea upon heating in DMSO in the presence of weak acid. The 1,8-di-uracil substituted cyclam gave a tricyclic dihydroimidazolium salt under the same conditions. These reactions can be explained by an intramolecular uracil ring-breaking reaction mechanism. |
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Keywords: | Cyclen Cyclam Uracil Tricyclic onium salt |
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