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Issue 15, 2017
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Domino reaction of cyclic sulfamidate imines with Morita–Baylis–Hillman acetates promoted by DABCO: a metal-free approach to functionalized nicotinic acid derivatives

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Abstract

A facile, green, metal-free new one-pot synthetic strategy has been developed for easy access to a wide array of medicinally promising functionalized pyridines having an ester, a nitrile or an acetyl group at the C-3 position in good to excellent yields via a domino SN2/elimination/6π-aza-electrocyclization/aromatization reaction of several 4-aryl/hetero-aryl-substituted 5-membered cyclic sulfamidate imines with a broad range of MBH acetates of acrylate/acrylonitrile/MVK in 2-MeTHF promoted by DABCO as an organobase under an O2 atmosphere. Moreover, a biologically interesting triazolopyridine derivative was achieved through a unique procedure.

Graphical abstract: Domino reaction of cyclic sulfamidate imines with Morita–Baylis–Hillman acetates promoted by DABCO: a metal-free approach to functionalized nicotinic acid derivatives

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Publication details

The article was received on 31 Jan 2017, accepted on 20 Mar 2017 and first published on 22 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00240H
Org. Biomol. Chem., 2017,15, 3286-3297

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    Domino reaction of cyclic sulfamidate imines with Morita–Baylis–Hillman acetates promoted by DABCO: a metal-free approach to functionalized nicotinic acid derivatives

    D. Majee, S. Biswas, S. M. Mobin and S. Samanta, Org. Biomol. Chem., 2017, 15, 3286
    DOI: 10.1039/C7OB00240H

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