Issue 10, 2015

CuSO4d-glucose, an inexpensive and eco-efficient catalytic system: direct access to diverse quinolines through modified Friedländer approach involving SNAr/reduction/annulation cascade in one pot

Abstract

A highly efficient and scalable multicomponent domino reaction for the synthesis of functionalized/annulated quinolines is devised directly from 2-bromoaromatic aldehydes/ketones in H2O–EtOH mixture for the first time. The key to this reaction is the use of an air-stable, eco-efficient and inexpensive CuSO4D-glucose catalyst system, which is able to catalyze multiple transformations in one pot. The approach is carbon-economic and relies on sequential SNAr/reduction/Friedländer annulation steps, forming C–C and C–N bonds by cleavage of the Csp2–Br bond in a single synthetic operation. The reaction has a broad substrate scope and affords products in good to excellent yields.

Graphical abstract: CuSO4–d-glucose, an inexpensive and eco-efficient catalytic system: direct access to diverse quinolines through modified Friedländer approach involving SNAr/reduction/annulation cascade in one pot

Supplementary files

Article information

Article type
Paper
Submitted
08 Nov 2014
Accepted
15 Dec 2014
First published
15 Dec 2014

RSC Adv., 2015,5, 7654-7660

CuSO4D-glucose, an inexpensive and eco-efficient catalytic system: direct access to diverse quinolines through modified Friedländer approach involving SNAr/reduction/annulation cascade in one pot

N. Anand, T. Chanda, S. Koley, S. Chowdhury and M. S. Singh, RSC Adv., 2015, 5, 7654 DOI: 10.1039/C4RA14138E

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