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

The sodium salts of the conjugated bases of uracils undergo highly chemoselective O4-monoalkylation when treated with various alkyl halides in dry DMF, while the use of methyl iodide results in N1+N3-dimethylation. Theoretical evaluations of the chemo- and regioselectivity along with X-ray crystallo...

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Bibliographic Details
Published in:Tetrahedron 2013-09, Vol.69 (39), p.8470-8476
Main Authors: Bakavoli, Mehdi, Eshghi, Hossein, Shiri, Ali, Afrough, Toktam, Tajabadi, Javad
Format: Article
Language:English
Subjects:
6-Methyl uracil
Drying
GIAO 13C NMR
Halides
HMDS
Iodides
O-Alkylation
Sodium salts
Synthesis
Tetrahedrons
Uracil
X-rays
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Summary:The sodium salts of the conjugated bases of uracils undergo highly chemoselective O4-monoalkylation when treated with various alkyl halides in dry DMF, while the use of methyl iodide results in N1+N3-dimethylation. Theoretical evaluations of the chemo- and regioselectivity along with X-ray crystallographic data are presented. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.07.025