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. 2012:8:1839-43.
doi: 10.3762/bjoc.8.211. Epub 2012 Oct 26.

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

Jing Sun  1 , Hong Gao, Qun Wu, Chao-Guo Yan
Affiliations

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

Jing Sun et al. Beilstein J Org Chem. 2012.

Abstract

In the presence of p-toluenesulfonic acid as catalyst the domino reaction of arylamines, methyl propiolates and aromatic aldehydes in ethanol proceeded smoothly to give polysubstituted 1,2,3,4-tetrahydroquinolines in moderate yields. The reaction is believed to involve the Povarov reaction of in situ generated β-enamino ester with the in situ formed aromatic imine.

Keywords: Povarov reaction; domino reaction; electron-deficient alkyne; tetrahydroquinoline; β-enamino ester.

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Figures

Scheme 1
Scheme 1
Synthesis of polysubstituted tetrahydroquinolines 1a–1m.
Figure 1
Figure 1
Molecular structure of compound 1c.
Scheme 2
Scheme 2
The proposed mechanism of domino Povarov reaction.
See this image and copyright information in PMC

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