TY - JOUR T1 - Highly regioselective C4-hydrazinylation of 2,4-dichloroquinolines: expedient synthesis of aminoquinoline substituted pyrrolidin-2,5-diones via hydrazinylquinolines JF - Tetrahedron Letters Y1 - 2014 A1 - Kumar, Gopal Senthil A1 - Zeller, Matthias A1 - Gonnade, Rajesh Ghanshyam A1 - Prasad, Kamam Jayarampillai Rajendra KW - 5-diones KW - Eaton's reagent KW - Hydrazinylquinolines KW - Pyrrolidin-2 KW - Regioisomers KW - SNAr reaction AB -

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.

PB - PERGAMON-ELSEVIER SCIENCE LTD CY - THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND VL - 55 IS - 30 U3 - Foreign U4 - 2.68 ER -