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通过 Au(III)催化的区域选择性 6-endo-环封闭反应,从邻炔基醛立体选择性串联合成噻唑并并萘啶和噻吩并吡啶。

Stereoselective tandem synthesis of thiazolo fused naphthyridines and thienopyridines from o-alkynylaldehydes via Au(III)-catalyzed regioselective 6-endo-dig ring closure.

机构信息

Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India.

出版信息

Org Biomol Chem. 2014 Jan 28;12(4):552-6. doi: 10.1039/c3ob42035c.

Abstract

An operationally simple approach for the stereoselective tandem synthesis of novel thiazolo fused naphthyridines and thienopyridines by the reaction of o-alkynylaldehydes with L-cystine methyl ester hydrochloride via Au(III)-catalyzed regioselective 6-endo-dig ring closure under mild reaction conditions is described. It is noteworthy that alkynes bearing an alkyl and a strong electron-withdrawing nitro group successfully afforded the desired products in good yields.

摘要

一种操作简单的方法,通过 Au(III)催化的区域选择性 6-endo-dig 环闭合反应,在温和的反应条件下,由邻炔基醛与 L-胱氨酸甲酯盐酸盐反应,立体选择性地串联合成新型噻唑并并萘啶和噻吩吡啶。值得注意的是,带有烷基和强吸电子硝基的炔烃成功地以良好的产率得到了所需的产物。

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