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.
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.
authors.affiliation: Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
authors.forename: Abdullah M A
authors.initials: AM
authors.lastname: Al Majid
authors.affiliation: Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
authors.forename: Mohammad Shahidul
authors.initials: MS
authors.lastname: Islam
authors.affiliation: 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.
authors.forename: Assem
authors.initials: A
authors.lastname: Barakat
authors.affiliation: Division of Microbiology, Pharmaceutics Department, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
authors.forename: Mohamed H M
authors.initials: MH
authors.lastname: Al-Agamy
authors.affiliation: Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
authors.forename: Mu
authors.initials: M
authors.lastname: Naushad
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis*; D003998:Dicarboxylic Acids / Q000138:chemical synthesis*; D004926:Escherichia coli / Q000187:drug effects; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000475:Alkenes; D000890:Anti-Infective Agents; D003521:Cyclopropanes; D003998:Dicarboxylic Acids; C574348:Feist's acid; D007211:Indoles; D011758:Pyrroles