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Microwave-Assisted Synthesis of Acyclic C -Nucleosides from 1,2- and 1,3-Diketones

2009; Taylor & Francis; Volume: 28; Issue: 3 Linguagem: Inglês

10.1080/15257770902830997

1532-2335

Najim A. Al‐Masoudi, Bahjat A. Saeed, Ali H. Essa, Yaseen A. Al‐Soud,

Microwave-Assisted Synthesis and Applications

A simple, rapid and regioselective approach for the synthesis of C-acyclic nucleosides 3, 4, 6, and 9 of dihydropyrimidine, imidazole and indeno[1,2-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, ZnCl(2), NH(4)OAc, or NH(4)NO(3), 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.