title: A green, multicomponent, regio- and stereo-selective 1,3-dipolar cycloaddition of azides and azomethine ylides generated in situ with bifunctional dipolarophiles using PEG-400.
abstract: A series of novel dispiropyrrolidine-linked 1,2,3-triazole derivatives have been prepared by one-pot, four-component protocol that employed 5-arylidene-3-(prop-2-ynyl)thiazolidine-2,4-dione, isatin, sarcosine and substituted azides using Cu(I) generated in situ as catalyst in PEG-400 as a highly efficient and green media. This is the first report of a four-component reaction involving a classical Huisgen reaction, in which the two dipolar moieties (substituted azides and in situ generated azomethine ylides) react with acetylenic and olefinic dipolarophiles, respectively. The 1,3-dipolar cycloaddition proceeds in a highly regio- and stereo-selective manner. This methodology can be an ideal tool for the preparation of biologically important five-membered heterocyclic compounds in one pot.
authors.affiliation: Department of Chemistry, University of Delhi, Delhi, 110007, India.
authors.forename: Jayant
authors.initials: J
authors.lastname: Sindhu
authors.forename: Harjinder
authors.initials: H
authors.lastname: Singh
authors.forename: J M
authors.initials: JM
authors.lastname: Khurana
mesh_terms: D001386:Azides / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D055772:Green Chemistry Technology; D008958:Models, Molecular; D008968:Molecular Conformation; D011092:Polyethylene Glycols / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013882:Thiosemicarbazones / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001386:Azides; D001391:Azo Compounds; D013882:Thiosemicarbazones; D014230:Triazoles; C512188:azomethine; D011092:Polyethylene Glycols; D003300:Copper