An Efficient Route to 4-Aryl-5-pyrimidinylimidazoles via Sequential Functionalization of 2,4-Dichloropyrimidine

Starting from 2,4-dichloropyrimidine, a concise synthetic route to medicinally important 4-aryl-5-pyrimidinylimidazoles is described. Sequential substitution of the 4- and 2-chloro groups using a regioselective Sonogashira coupling, followed by nucleophilic substitution, led to pyrimidinylalkyne der...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 2; pp. 269 - 272
Main Authors Deng, Xiaohu, Mani, Neelakandha S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.01.2006
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Hydrocarbons, Chlorinated - chemistry
Imidazoles - chemical synthesis
Molecular Structure
Physical Sciences
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Science & Technology
OXIDATION
POTASSIUM-PERMANGANATE
SELECTIVE INHIBITOR
POTENT
ACTIVATED PROTEIN-KINASE
HYDROCARBONS
1,2-DIKETONES
IMIDAZOLES
SORBITOL DEHYDROGENASE INHIBITORS
P38 MAP KINASE
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Summary:Starting from 2,4-dichloropyrimidine, a concise synthetic route to medicinally important 4-aryl-5-pyrimidinylimidazoles is described. Sequential substitution of the 4- and 2-chloro groups using a regioselective Sonogashira coupling, followed by nucleophilic substitution, led to pyrimidinylalkyne derivatives, which were then oxidized to their corresponding 1,2-diketones. These 1,2-diketones, on cyclocondensation with ammonium acetate and an aldehyde, furnished the desired pyrimidinyl imidazoles in good overall yields.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol052663x