最新论文
更多信息
[已阅读583次]
病毒免疫药物药理学课题组习保民副教授以共同通讯作者在Journal of Organic chemistry 发表论文

病毒免疫药物药理学课题组习保民副教授以共同通讯作者在

Journal of Organic chemistry 发表论文

 

    近日,病毒免疫药物药理学课题组习保民副教授以共同通讯作者在Journal of Organic chemistry杂志上发表题目为“Synthesis of Carbazoles and Carbazole-Containing Heterocycles via Rhodium-Catalyzed Tandem Carbonylative Benzannulations.”的研究性论文。

    多环芳香族化合物是许多药物和其他材料的重要组成部分。课题组发展了一系列铑催化芳基炔丙醇与羰基串联合成不同种类的三,四,五芳(杂)环反应。本论文利用这些串联反应能高效获得取代的咔唑、呋喃并咔唑、吡咯并咔唑、噻吩并咔唑、吲哚并咔唑类化合物。三环杂环化合物可由乙烯芳基丙炔醇合成,四,五环杂环化合物可由二芳基丙炔醇制备。羰基串联芳环化反应的机理为:π酸性铑(I)对炔基加成生成关键中间体金属卡宾,接着被CO捕获形成烯酮并进行6π电子环化。总的来说,本反应通过铑催化羰基串联苯环化反应新生成3个化学键及2个环。

    该论文受美国自然科学基金NSF (CHE-1464754) 及南方医科大学出国留学基金资助。论文由习保民及UW-Madison药学院的Weiping Tang为共同通讯作者。Journal of Organic chemistry为II区杂志,IF=4.79。

Wangze Song, Xiaoxun Li, Ka Yang, Xian-liang Zhao, Daniel A. Glazier, Bao-min Xi,* Weiping Tang*,  Synthesis of Carbazoles and Carbazole-Containing Heterocycles via Rhodium-Catalyzed Tandem Carbonylative Benzannulations.  Journal of Organic Chemistry. 2016, 81, 2930−2942.

Abstract

Polycyclic aromatic compounds are important constituents of pharmaceuticals and other materials. We have developed a series of Rh-catalyzed tandem carbonylative benzannulations for the synthesis of tri-, tetra-, and pentacyclic heterocycles from different types of aryl propargylic alcohols. These tandem reactions provide efficient access to highly substituted carbazoles, furocarbazoles, pyrrolocarbazoles, thiophenocarbazoles, and indolocarbazoles. While tricyclic heterocycles could be derived from vinyl aryl propargylic alcohols, tetra- and pentacyclic heterocycles

were synthesized from diaryl propargylic alcohols. The tandem carbonylative benzannulation is initiated by a π-acidic rhodium(I) catalyst-mediated nucleophilic addition to alkyne to generate a key metal-carbene intermediate, which is then trapped by carbon monoxide to form a ketene species for 6π electrocyclization. Overall, three bonds and two rings are formed in all of these tandem carbonylative benzannulation reactions.