Facile and promising method for michael addition of indole and pyrrole to electron-deficient trans-?-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-?-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 ?-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.

SUBMITTER: Al Majid AM 

PROVIDER: S-EPMC3915498 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature