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

• Published in: TheScientificWorld Vol. 2014; no. 2014; pp. 1 - 15
• Main Authors: Naushad, M., al-Agamy, Mohamed H., Barakat, Assem, Islam, Mohammad Shahidul, Al Majid, Abdullah M. A.
• Format: Journal Article
• Language: English
• Published: Cairo, Egypt Hindawi Publishing Corporation 01.01.2014; Hindawi Limited
• Subjects: Alkenes - chemical synthesis; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - pharmacology; Bacillus subtilis - drug effects; Candida albicans - drug effects; Catalysis; Cyclopropanes - chemical synthesis; Dicarboxylic Acids - chemical synthesis; Escherichia coli - drug effects; Hydrogen Bonding; Indoles - chemical synthesis; Pyrroles - chemical synthesis; Staphylococcus aureus - drug effects
• ISSN: 2356-6140; 1537-744X
• DOI: 10.1155/2014/649197

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.