Microwave-Assisted Synthesis of Acyclic C-Nucleosides from 1,2- and 1,3-Diketones |
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| Authors: | Najim A Al-Masoudi Bahjat A Saeed Ali H Essa Yaseen A Al-Soud |
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| Institution: | 1. Fachbereich Chemie , Universit?t Konstanz , Konstanz, Germany;2. Department of Chemistry , College of Education, University of Basrah , Basrah, Iraq;3. Department of Chemistry , College of Science, University of Basrah , Basrah, Iraq;4. Department of Chemistry , College of Science, University of Al al-Bayt , Al-Mafraq, Jordan |
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| Abstract: | A simple, rapid and regioselective approach for the synthesis of C-acyclic nucleosides 3, 4, 6, and 9 of dihydropyrimidine, imidazole and indeno1,2-b]pyridine-9-one derived from 1,2- and 1,3-diketones was performed. By using DMF or pyridine as solvent or bentonite clay as a support, in the presence of TMSTf, ZnCl2, NH4OAc, or NH4NO3, all the desired products were obtained within 5–25 minutes under microwave irradiation (MWI). Acid hydrolysis of 6 and 9 afforded the free acyclic C-nucleosides 7 and 10, respectively. Upon treatment with NaOMe under MWI, 3 and 14 rearranged to the C-nucleoside 4 and 16. |
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| Keywords: | Acyclic C-nucleosides Beginelli reaction ß-diketones microwave-assisted synthesis pyrimidinones |
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