Synthesis of Mannich type products via a three-component coupling reaction

doi:10.1016/j.tetlet.2005.01.118

Tetrahedron Letters

Volume 46, Issue 12, 21 March 2005, Pages 2137-2140

https://doi.org/10.1016/j.tetlet.2005.01.118 Get rights and content

Abstract

The reactions of alkyl nitriles, acetyl chloride, aldehydes and β-ketoesters or simple ketones was studied for the one-pot synthesis of β-acetamido carbonyl compounds. It was observed that the reaction proceeds in the absence of Lewis acids. However, a Lewis acid catalyzes the reaction and several were tested. It was found that whereas Cu(OTf)₂ is suitable for the coupling of β-ketoesters with aldehydes, Sc(OTf)₃ is the best for ketones. A possible mechanism is proposed based on the isolation and characterization of an intermediate.

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Acknowledgements

V.K.S. thanks the Department of Science and Technology, India for a research grant. G.P., A.G. and R.P.S. thank CSIR for research fellowships.

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Synthesis of Mannich type products via a three-component coupling reaction

Abstract

Graphical abstract

Section snippets

Acknowledgements

Acc. Chem. Res.

Angew. Chem., Int. Ed.

Tetrahedron

Acc. Chem. Res.

Chem. Rev.

Acc. Chem. Res.

Liebigs Ann. Chem.

J. Org. Chem.