Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C–H bond activation

A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C–H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as t...

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Bibliographic Details
Published inTetrahedron Vol. 69; no. 4; pp. 1387 - 1396
Main Authors Cheng, Chien, Shih, Yu-Chiao, Chen, Hui-Ting, Chien, Tun-Cheng
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.01.2013
Elsevier
Subjects
4-Pyridone
Arylation
Catalysis
Chemistry
Chemistry, Organic
C–H activation
Physical Sciences
Science & Technology
Uracil
Arylation
C–H activation
4-Pyridone
Catalysis
Uracil
PALLADIUM
ANALOGS
NUCLEOSIDES
CATALYZED ARYLATION
GENERAL-METHOD
ARYL BROMIDES
C-H activation
OROTIDINE 5'-MONOPHOSPHATE DECARBOXYLASE
IRREVERSIBLE ENZYME-INHIBITORS
ANTIVIRAL ACTIVITY
THYMIDINE PHOSPHORYLASE
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Summary:A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C–H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.11.001