Synlett 2005(6): 1018-1020  
DOI: 10.1055/s-2005-864810
LETTER
© Georg Thieme Verlag Stuttgart · New York

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;
Weitere Informationen

Publikationsverlauf

Received 7 January 2005
Publikationsdatum:
23. März 2005 (online)

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.

16

The three-component reaction of benzaldehyde, benzhydrylamine and diene afforded 67% yield in toluene compared to 77% yield without solvent.