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N-乙烯基苯并三唑的模块化合成。

Modular synthesis of N-vinyl benzotriazoles.

机构信息

Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, New York 10031-9198, USA.

出版信息

Org Lett. 2013 Aug 16;15(16):4086-9. doi: 10.1021/ol401661j. Epub 2013 Aug 5.

DOI:10.1021/ol401661j
PMID:23915255
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4247791/
Abstract

A modular approach to N1-vinyl benzotriazoles by azide-aryne cycloadditions and Julia-Kocienski reactions is described. Reactions of azidomethyl phenyl-1H-tetrazol-5-yl (PT) sulfide with arynes gave methyl(PT-sulfanyl)-substituted benzotriazoles in 68-89% yields. Oxidation of the sulfides to the sulfones gave the benzotriazole-substituted Julia-Kocienski reagents. Olefination reactions of aldehydes and a ketone with reagents derived from benzyne, 2,3-naphthyne, and 4,5-dimethoxybenzyne precursors proceeded to give various N1-vinyl benzotriazole derivatives. Olefination stereoselectivities are tunable for electron-rich aldehydes, but not for electron-deficient aldehydes and alkanals, where they proceed with good to excellent Z-stereoselectivity.

摘要

通过叠氮-芳炔环加成和 Julia-Kocienski 反应实现 N1-乙烯基苯并三唑的模块化方法。将叠氮甲基苯-1H-四唑-5-基（PT）硫醚与芳炔反应，以 68-89%的收率得到甲基（PT-硫基）取代的苯并三唑。将硫醚氧化成亚砜得到苯并三唑取代的 Julia-Kocienski 试剂。来自苯炔、2,3-萘炔和 4,5-二甲氧基苯炔前体的试剂与醛和酮的烯烃化反应得到各种 N1-乙烯基苯并三唑衍生物。对于富电子醛，烯烃化立体选择性是可调的，但对于缺电子醛和烷醛，则具有良好到优异的 Z-立体选择性。

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