Microwave-assisted ring opening of epoxides with pyrimidine nucleobases:: A rapid entry into C-nucleoside synthesis

被引：48

作者：

Khalafi-Nezhad, A ^{[1
]}

Rad, MNS ^{[1
]}

Khoshnood, A ^{[1
]}

机构：

[1] Shiraz Univ, Dept Chem, Coll Sci, Shiraz 71454, Iran

来源：

SYNTHESIS-STUTTGART | 2004年 / 04期

关键词：

microwave; uracil; epoxides; TBAB; magnesium oxide;

D O I：

10.1055/s-2004-815968

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Microwave irradiation strongly accelerates the regioselective nucleophilic ring opening of epoxides by pyrimidine nucleobases. In the presence of tetrabutyl ammonium bromide (TBAB), various bases were elaborated to determine the proper base in which it can activate N1 rather than N3 for alkylation. It was shown that MgO not only could serve as an eligible base, but also enhanced the selectivity and tendency of N1 for alkylation as compared with N3. The use of microwave irradiation provided dominant regioselective synthesis of N1-beta-hydroxyalkylpyrimidines in moderate to good yields with a reaction time of less than 7 minutes.

引用

页码：583 / 589

页数：7

共 42 条

[1]

AHLUWALIA VK, 2001, ORGANIC SYNTHESIS SP, P90

[2]

Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis [J].