Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles

Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of...

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Bibliographic Details
Published in:Tetrahedron 2011-09, Vol.67 (38), p.7370-7378
Main Authors: Semenov, Vyacheslav E., Krylova, Evgeniya S., Galyametdinova, Irina V., Chernova, Alla V., Kharlamov, Sergey V., Latypov, Shamil K., Reznik, Vladimir S.
Format: Article
Language:English
Subjects:
Alkylation
Heterocycles
Heterocyclophanes
Isomers
Macrocyclic compounds
Nuclear magnetic resonance
Structure elucidation
Synthesis (chemistry)
Terminals
Tetrahedrons
Uracil
Uracils
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Summary:Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of macrocyclic regioisomers were unambiguously determined by NMR data. One of the regioisomers exhibits a hypochromic effect with respect to model compounds. The acyclic uracils obtained bridged with five-membered heterocycles are alkylated with methyliodide and methyl tosylate, and oxidated with m-CPBA, H 2O 2, and I 2. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.07.034