Issue 4, 2016

Efficient synthesis of 2-acylquinolines based on an aza-vinylogous Povarov reaction

Abstract

The aza-vinylogous Povarov reaction between α-ketoimines and α,β-unsaturated dimethylhydrazones in the presence of indium trichloride affords 2-acyl-4-alkyl-4-dimethylhydrazonomethyl-1,2,3,4-tetrahydroquinolines with good cis/trans diastereoselectivities. These compounds were readily transformed into highly substituted 2-acylquinolines using a two-reaction sequence involving the oxidative generation of a C-4 nitrile group, followed by its elimination under thermal conditions. Alternatively, a one-pot protocol based on the reaction of hydrazones with magnesium monoperoxyphthalate hexahydrate in refluxing methanol afforded the target 2-acylquinolines in good to excellent yields. This methodology was also extended to the preparation of 2-arylquinolines.

Graphical abstract: Efficient synthesis of 2-acylquinolines based on an aza-vinylogous Povarov reaction

Supplementary files

Article information

Article type
Research Article
Submitted
21 jan 2016
Accepted
15 feb 2016
First published
15 feb 2016

Org. Chem. Front., 2016,3, 412-422

Efficient synthesis of 2-acylquinolines based on an aza-vinylogous Povarov reaction

G. Bianchini, P. Ribelles, D. Becerra, M. T. Ramos and J. C. Menéndez, Org. Chem. Front., 2016, 3, 412 DOI: 10.1039/C6QO00037A

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