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Issue 16, 2015
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An “all-water” strategy for regiocontrolled synthesis of 2-aryl quinoxalines

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Abstract

A new synthetic strategy of tandem N-aroylmethylation-nitro reduction–cyclocondensation has been developed for the first and generalized regioselective synthesis of 2-aryl quinoxalines adopting “all water chemistry.” Water plays the critical role through hydrogen bond driven ‘synergistic electrophile–nucleophile dual activation’ for chemoselective N-aroylmethylation of o-nitroanilines, that underlines the origin of the regioselectivity, as the use of organic solvents proved to be ineffective. Water also provides beneficial effects during the nitro reduction and the penultimate cyclocondensation steps.

Graphical abstract: An “all-water” strategy for regiocontrolled synthesis of 2-aryl quinoxalines

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Publication details

The article was received on 17 Dec 2014, accepted on 09 Jan 2015 and first published on 09 Jan 2015


Article type: Paper
DOI: 10.1039/C4RA16568C
Citation: RSC Adv., 2015,5, 11873-11883
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    An “all-water” strategy for regiocontrolled synthesis of 2-aryl quinoxalines

    B. Tanwar, P. Purohit, B. N. Raju, D. Kumar, D. N. Kommi and A. K. Chakraborti, RSC Adv., 2015, 5, 11873
    DOI: 10.1039/C4RA16568C

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