1,3-dipolar cycloaddition reactions in the series of N-alkynyl-substituted uracils

Reactions of 1-( ω -bromoalkyl)-3,6-dimethyluracils and 1,3-bis( ω -bromoalkyl)-6-methyluracils with sodium azide gave the corresponding mono- and bis-azides. 1,3-Dipolar cycloaddition of the latter with prop-2-yn-1-ol, hex-1-yne, and dec-1-yne in the presence of copper(I) ions afforded acyclic and...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2012-04, Vol.48 (4), p.582-587
Main Authors: Semenov, V. E., Nikolaev, A. E., Krylova, E. S., Sharafutdinova, D. R., Reznik, V. S.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Reactions of 1-( ω -bromoalkyl)-3,6-dimethyluracils and 1,3-bis( ω -bromoalkyl)-6-methyluracils with sodium azide gave the corresponding mono- and bis-azides. 1,3-Dipolar cycloaddition of the latter with prop-2-yn-1-ol, hex-1-yne, and dec-1-yne in the presence of copper(I) ions afforded acyclic and macrocyclic uracil derivatives containing 1,4-disubstituted 1,2,3-triazole fragments, which were subjected to quaternization with propyl iodide and methyl p -toluenesulfonate at the 1,2,3-triazole nitrogen atom.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428012040203