A Mild and Efficient Synthesis of 2,5-Disubstituted 2,3-Dihydro-4-pyridones Catalyzed by Yb(OTf)3

Ke Cheng; Baiqing Zeng; Zhipeng Yu; Bo Gao; Xiaoming Feng

doi:10.1055/s-2005-864810

LETTER

A Mild and Efficient Synthesis of 2,5-Disubstituted 2,3-Dihydro-4-pyridones Catalyzed by Yb(OTf)₃

Ke Cheng, Baiqing Zeng, Zhipeng Yu, Bo Gao, Xiaoming Feng*
Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
e-Mail: xmfeng@scu.edu.cn;

Abstract

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Abstract

A highly efficient aza-Diels-Alder reaction of trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene with N-benzhydryl imines was catalyzed by Yb(OTf)₃ in toluene at room temperature to give corresponding 2,5-disubstituted 2,3-dihydro-4-pyridones in high yields. Three-component reactions of diene with aldehydes and amines were also performed smoothly to afford the desired cycloadducts under solvent-free condition in 51-86% yields.

Key words

Diels-Alder reaction - N-benzhydryl imines - solvent-free - Lewis acid - three-component reaction

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References

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