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

被引：13

作者：

Al-Masoudi, Najim A. ^{[1
,3
]}

Saeed, Bahjat. A. ^{[2
]}

Essa, Ali H. ^{[3
]}

Al-Soud, Yaseen A. ^{[4
]}

机构：

[1] Univ Konstanz, Fachbereich Chem, Constance, Germany

[2] Univ Basrah, Coll Educ, Dept Chem, Basrah, Iraq

[3] Univ Basrah, Coll Sci, Dept Chem, Basrah, Iraq

[4] Univ Al Al Bayt, Coll Sci, Dept Chem, Al Mafraq, Jordan

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2009年 / 28卷 / 03期

关键词：

Acyclic C-nucleosides; Beginelli reaction; ss-diketones; microwave-assisted synthesis; pyrimidinones; BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS; ANTIVIRAL AGENTS; ANALOGS; DERIVATIVES; ACYCLOVIR; CHEMISTRY; 9-(2-HYDROXYETHOXYMETHYL)GUANINE; 1,4-DIHYDROPYRIDINES; EFFICIENT;

D O I：

10.1080/15257770902830997

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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, 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.

引用

页码：175 / 183

页数：9

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