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

TitleHighly regioselective C4-hydrazinylation of 2,4-dichloroquinolines: expedient synthesis of aminoquinoline substituted pyrrolidin-2,5-diones via hydrazinylquinolines
Publication TypeJournal Article
Year of Publication2014
AuthorsKumar, GSenthil, Zeller, M, Gonnade, RGhanshyam, Prasad, KJayarampil
JournalTetrahedron Letters
Volume55
Issue30
Pagination4240-4244
Date PublishedJUL
ISSN0040-4039
Keywords5-diones, Eaton's reagent, Hydrazinylquinolines, Pyrrolidin-2, Regioisomers, SNAr reaction
Abstract

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 C-4 rather than C-2 position of dichloroquinolines. The hydrazinylquinolines were subsequently converted into aminoquinoline substituted pyrrolidin-2,5-diones in the presence of Eaton's reagent. (C) 2014 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2014.05.132
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.68
Divison category: 
Center for Material Characterization (CMC)