Highly regioselective C4-hydrazinylation of 2,4-dichloroquinolines: expedient synthesis of aminoquinoline substituted pyrrolidin-2,5-diones via hydrazinylquinolines

A new class of hydrazinylquinoline regio-isomers has been synthesized through SNAr reaction of 2,4-dichloroquinolines with hydrazine hydrate. The reaction stops at the mono-substitution product with high regioselectivity at the C4 rather than C2 position of dichloroquinolines. The hydrazinylquinolin...

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Bibliographic Details
Published in:Tetrahedron letters 2014-07, Vol.55 (30), p.4240-4244
Main Authors: Senthil Kumar, Gopal, Zeller, Matthias, Gonnade, Rajesh Ghanshyam, Rajendra Prasad, Karnam Jayarampillai
Format: Article
Language:English
Subjects:
Aminoquinolines
Eaton’s reagent
Hydrates
Hydrazines
Hydrazinylquinolines
Plugs
Pyrrolidin-2,5-diones
Regioisomers
SNAr reaction
Synthesis (chemistry)
Tetrahedrons
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Summary:A new class of hydrazinylquinoline regio-isomers has been synthesized through SNAr reaction of 2,4-dichloroquinolines with hydrazine hydrate. The reaction stops at the mono-substitution product with high regioselectivity at the C4 rather than C2 position of dichloroquinolines. The hydrazinylquinolines were subsequently converted into aminoquinoline substituted pyrrolidin-2,5-diones in the presence of Eaton’s reagent.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.05.132