Efficient synthesis of 2-acylquinolines based on an aza-vinylogous Povarov reaction
Literature Information
Publication Date
2016-02-15
DOI
10.1039/C6QO00037A
Impact Factor
5.281
Authors
Giulia Bianchini, Pascual Ribelles, M. Teresa Ramos, J. Carlos Menéndez
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
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8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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Molecular Formula:
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