Convenient synthesis of perfluoroalkyl substituted 2-oxopyridine-fused 1,3-diazaheterocycles via a one-pot three-component reaction

An efficient one-pot synthesis of perfluoroalkylated ring-fused 2-pyridones by three-component reaction of diamine, ketene dithioacetal, and methyl 2-perfluoroalkynoate in EtOH is reported. This protocol has the advantages of easiness, higher yields, and shorter reaction time. A plausible mechanism...

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Bibliographic Details
Published in:Tetrahedron 2013-05, Vol.69 (21), p.4270-4275
Main Authors: Wang, Zewei, Sun, Tianqi, Chen, Jie, Deng, Hongmei, Shao, Min, Zhang, Hui, Cao, Weiguo
Format: Article
Language:English
Subjects:
Diamines
Ketene dithioacetal
Ketenes
Methyl 2-perfluoroalkynoate
Multicomponent reaction
One-pot synthesis
Perfluoroalkylated ring-fused 2-pyridone
Perfluoroalkyls
Reaction time
Synthesis
Tetrahedrons
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Summary:An efficient one-pot synthesis of perfluoroalkylated ring-fused 2-pyridones by three-component reaction of diamine, ketene dithioacetal, and methyl 2-perfluoroalkynoate in EtOH is reported. This protocol has the advantages of easiness, higher yields, and shorter reaction time. A plausible mechanism for this type of cyclization is proposed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.03.080