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

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 ?-enamino ester with the in situ formed aromatic imine.

SUBMITTER: Sun J

PROVIDER: S-EPMC3511020 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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

Sun Jing J Gao Hong H Wu Qun Q Yan Chao-Guo CG

Beilstein journal of organic chemistry 20121026

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. ...[more]

PMID: 23209520

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