Synthesis, characterization and theoretical evaluations of HMDS promoted chemoselective O-alkylation of uracils

被引：4

作者：

Bakavoli, Mehdi ^{[1
]}

Eshghi, Hossein ^{[1
]}

Shiri, Ali ^{[1
]}

Afrough, Toktam ^{[1
]}

Tajabadi, Javad ^{[1
]}

机构：

[1] Ferdowsi Univ Mashhad, Sch Sci, Dept Chem, Mashhad 917751436, Iran

来源：

TETRAHEDRON | 2013年 / 69卷 / 39期

关键词：

6-Methyl uracil; HMDS; O-Alkylation; GIAO C-13 NMR; CHEMICAL-SHIFTS; C-13; H-1;

D O I：

10.1016/j.tet.2013.07.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sodium salts of the conjugated bases of uracils undergo highly chemoselective O-4-monoalkylation when treated with various alkyl halides in dry DMF, while the use of methyl iodide results in N-1+N-3-dimethylation. Theoretical evaluations of the chemo- and regioselectivity along with X-ray crystallographic data are presented. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：8470 / 8476

页数：7

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