Microwave-assisted synthesis of acyclic C-nucleosides from 1,2- and 1,3-diketones.

Research paper by Najim A NA Al-Masoudi, Bahjat A BA Saeed, Ali H AH Essa, Yaseen A YA Al-Soud

Indexed on: 01 Apr '09Published on: 01 Apr '09Published in: Nucleosides, nucleotides & nucleic acids


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.