A novel class of sugar-based ether-linked-dispirooxindolo-pyrrolidines/pyrrolizidines through [3+2]-cycloaddition of azomethine ylides

An efficient one-pot synthesis of novel sugar based dispirooxindolo-pyrrolidines/pyrrolizidines has been accomplished by a [3+2]-cycloaddition. This method utilizes an azomethine ylide derived from isatin and sarcosine/L-proline, with an ether linked alpha-, beta-unsaturated-beta-C-glycosidic ketones as the dipolarophile. All these sugar-based heterocyclics were characterized by NMR (H-1 and C-13) and elemental analysis. Antimicrobial studies of sugar based dispiroheterocyclic compound 10 shows excellent activity against different microbes. (C) 2012 Elsevier Ltd. All rights reserved.