Highly regioselective C4-hydrazinylation of 2,4-dichloroquinolines: expedient synthesis of aminoquinoline substituted pyrrolidin-2,5-diones via hydrazinylquinolines |
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| Authors: | Gopal Senthil Kumar Matthias Zeller Rajesh Ghanshyam Gonnade Karnam Jayarampillai Rajendra Prasad |
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| Affiliation: | 1. Department of Chemistry, Bharathiar University, Coimbatore 641046, India;2. Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, OH 44555, USA;3. Center for Materials Characterization, National Chemical Laboratory, (CSIR-NCL), Pune, India |
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| 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 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. |
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| Keywords: | SNAr reaction Regioisomers Hydrazinylquinolines Pyrrolidin-2,5-diones Eaton&rsquo s reagent |
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