Efficient acid catalytic synthesis of pyrazolopyrimidines from 1H-pyrazol-5-yl-N,N-dimethylformamidines with cyanamide |
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Authors: | Shuo-En Tsai Wan-Ping Yen Ching-Chun Tseng Jia-Jun Xie Ming Yu Liou Yi-Ting Li Naoto Uramaru Fung Fuh Wong |
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Institution: | 1. School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan;2. Ph.D. Program for Biotech Pharmaceutical Industry, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan;3. Master Program for Pharmaceutical Manufacture, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan;4. Department of Environmental Science, Nihon Pharmaceutical University, 10281, Komuro, Ina-machi, Kitaadachi-gun, Saitama, Japan |
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Abstract: | The efficient acid catalytic synthesis of pyrazolo 3,4-d]pyrimidine was developed by treating 1H-pyrazol-5-yl-N,N-dimethylformamidine with various aminating agents including N,O-bis(trimethylsilyl)hydroxylamine (NHSiMe3(OSiMe3)), cyanamide (NH2CN), hydroxylamine (NH2OH), methoxyamine (NH2OMe), hydrazine (NH2NH2), and urea (NH2C(O)NH2) in acidic solution at reflux. Based on the experimental result, cyanamide (NH2CN) and methanesulfonic acid were indicated the best aminating agent and acid mediated solvent. On the other hands, the reactivity tendency was involved the activity of original leaving species grafting on the aminating agents, such as –OH, –OMe, –OSiMe3, –NH2, –OSiMe3, –C(O)NH2, and –CN, in acid catalytic heterocyclic reaction. |
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Keywords: | Pyrazolopyrimidines Cyanamide Formamidines Heterocyclization |
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