title: A novel class of sugar-based ether-linked-dispirooxindolo-pyrrolidines/pyrrolizidines through [3+2]-cycloaddition of azomethine ylides.
abstract: 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 α-,β-unsaturated-β-C-glycosidic ketones as the dipolarophile. All these sugar-based heterocyclics were characterized by NMR ((1)H and (13)C) and elemental analysis. Antimicrobial studies of sugar based dispiroheterocyclic compound 10 shows excellent activity against different microbes.
authors.affiliation: Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
authors.forename: Arasappan
authors.initials: A
authors.lastname: Hemamalini
authors.forename: Subbiah
authors.initials: S
authors.lastname: Nagarajan
authors.forename: Thangamuthu
authors.initials: T
authors.lastname: Mohan Das
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001391:Azo Compounds / Q000737:chemistry*; D001419:Bacteria / Q000187:drug effects; D004987:Ethers / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D000078183:Oxindoles; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013379:Substrate Specificity; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D001391:Azo Compounds; D004987:Ethers; D006027:Glycosides; D007211:Indoles; D007659:Ketones; D000078183:Oxindoles; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine; C022960:2-oxindole