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Synlett 2005(6): 1018-1020
DOI: 10.1055/s-2005-864810
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
Weitere Informationen
Received
7 January 2005
Publikationsdatum:
23. März 2005 (online)
Publikationsverlauf
Publikationsdatum:
23. März 2005 (online)
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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
The three-component reaction of benzaldehyde, benzhydrylamine and diene afforded 67% yield in toluene compared to 77% yield without solvent.