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通过氢键供体催化剂费斯特酸催化吲哚和吡咯与缺电子反式-β-硝基烯烃进行迈克尔加成反应的简便且有前景的方法及抗菌活性初步研究

Facile and promising method for michael addition of indole and pyrrole to electron-deficient trans-β-nitroolefins catalyzed by a hydrogen bond donor catalyst Feist's acid and preliminary study of antimicrobial activity.

作者信息

Al Majid Abdullah M A, Islam Mohammad Shahidul, Barakat Assem, Al-Agamy Mohamed H M, Naushad Mu

机构信息

Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.

Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia ; Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt.

出版信息

ScientificWorldJournal. 2014 Jan 16;2014:649197. doi: 10.1155/2014/649197. eCollection 2014.

Abstract

The importance of cooperative hydrogen-bonding effects has been demonstrated using novel 3-methylenecyclopropane-1,2-dicarboxylic acid (Feist's acid (FA)) as hydrogen bond donor catalysts for the addition of indole and pyrrole to trans-β-nitrostyrene derivatives. Because of the hydrogen bond donor (HBD) ability, Feist's acid (FA) has been introduced as a new class of hydrogen bond donor catalysts for the activation of nitroolefin towards nucleophilic substitution reaction. It has effectively catalyzed the Michael addition of indoles and pyrrole to β-nitroolefins under optimum reaction condition to furnish the corresponding Michael adducts in good to excellent yields (up to 98%). The method is general, atom-economical, convenient, and eco-friendly and could provide excellent yields and regioselectivities. Some newly synthesized compounds were for examined in vitro antimicrobial activity and their preliminary results are reported.

摘要

利用新型3-亚甲基环丙烷-1,2-二羧酸(费斯特酸(FA))作为氢键供体催化剂,将吲哚和吡咯加成到反式-β-硝基苯乙烯衍生物上,证明了协同氢键效应的重要性。由于具有氢键供体(HBD)能力,费斯特酸(FA)已被引入作为一类新型的氢键供体催化剂,用于活化硝基烯烃以进行亲核取代反应。在最佳反应条件下,它有效地催化了吲哚和吡咯与β-硝基烯烃的迈克尔加成反应,以良好至优异的产率(高达98%)提供相应的迈克尔加成物。该方法具有通用性、原子经济性、方便且环保,能够提供优异的产率和区域选择性。对一些新合成的化合物进行了体外抗菌活性测试,并报告了其初步结果。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6abc/3915498/0960460c94aa/TSWJ2014-649197.sch.001.jpg

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