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
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 (...
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| Format: | Article |
| Language: | English |
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Wiley
2014-01-01
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| Series: | The Scientific World Journal |
| Online Access: | http://dx.doi.org/10.1155/2014/649197 |
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| author | Abdullah M. A. Al Majid Mohammad Shahidul Islam Assem Barakat Mohamed H. M. Al-Agamy Mu. Naushad |
| author_facet | Abdullah M. A. Al Majid Mohammad Shahidul Islam Assem Barakat Mohamed H. M. Al-Agamy Mu. Naushad |
| author_sort | Abdullah M. A. Al Majid |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-ba12ecc6d37c4aaead651c58e42b1cf7 |
| institution | Kabale University |
| issn | 2356-6140 1537-744X |
| language | English |
| publishDate | 2014-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | The Scientific World Journal |
| spelling | doaj-art-ba12ecc6d37c4aaead651c58e42b1cf72025-02-03T01:01:51ZengWileyThe Scientific World Journal2356-61401537-744X2014-01-01201410.1155/2014/649197649197Facile 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 ActivityAbdullah M. A. Al Majid0Mohammad Shahidul Islam1Assem Barakat2Mohamed H. M. Al-Agamy3Mu. Naushad4Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDivision of Microbiology, Pharmaceutics Department, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaThe 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.http://dx.doi.org/10.1155/2014/649197 |
| spellingShingle | Abdullah M. A. Al Majid Mohammad Shahidul Islam Assem Barakat Mohamed H. M. Al-Agamy Mu. Naushad 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 The Scientific World Journal |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| url | http://dx.doi.org/10.1155/2014/649197 |
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