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DABCO促进的环状氨基磺酸亚胺与Morita-Baylis-Hillman乙酸酯的多米诺反应:一种合成功能化烟酸衍生物的无金属方法。

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

作者信息

Majee Debashis, Biswas Soumen, Mobin Shaikh M, Samanta Sampak

机构信息

Discipline of Chemistry, Indian Institute of Technology Indore, Simrol, 453552, Indore, India.

出版信息

Org Biomol Chem. 2017 Apr 11;15(15):3286-3297. doi: 10.1039/c7ob00240h.

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 S2/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 O atmosphere. Moreover, a biologically interesting triazolopyridine derivative was achieved through a unique procedure.

摘要

已开发出一种简便、绿色、无金属的新型一锅法合成策略,通过几种4-芳基/杂芳基取代的五元环氨基磺酸酯亚胺与多种丙烯酸酯/丙烯腈/MVK的MBH乙酸酯在2-甲基四氢呋喃中,以DABCO作为有机碱,在氧气气氛下进行多米诺S2/消除/6π-氮杂电环化/芳构化反应,能够轻松获得多种在C-3位具有酯基、腈基或乙酰基的具有药用前景的功能化吡啶,产率良好至优异。此外,通过独特的方法得到了一种具有生物学意义的三唑并吡啶衍生物。

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