Issue 15, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
31 Jan 2017
Accepted
20 Mar 2017
First published
22 Mar 2017

Org. Biomol. Chem., 2017,15, 3286-3297

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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