title: Domino Prins/pinacol reaction for the stereoselective synthesis of spiro[pyran-4,4'-quinoline]-2',3'-dione derivatives.
abstract: A wide array of aldehydes undergo smooth cross-coupling with 3-hydroxy-3-(4-hydroxybut-1-en-2-yl)-1-methylindolin-2-one in the presence of 10 mol% BF3·OEt2 at 0 °C in dichloromethane to afford the corresponding 2,3,5,6-tetrahydro-1'H-spiro[pyran-4,4'-quinoline]-2',3'-dione derivatives in good yields with excellent diastereoselectivity. This is the first report on the synthesis of tetrahydro-1'H-spiro[pyran-4,4'-quinoline]-2',3'-dione scaffolds through a cascade of Prins/pinacol reactions.
authors.affiliation: Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India. basireddy@iict.res.in.
authors.forename: B V Subba
authors.initials: BV
authors.lastname: Reddy
authors.forename: S Gopal
authors.initials: SG
authors.lastname: Reddy
authors.forename: M
authors.initials: M
authors.lastname: Durgaprasad
authors.forename: Manika Pal
authors.initials: MP
authors.lastname: Bhadra
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D015363:Quinolones; D013141:Spiro Compounds; C000604287:spiro(pyran-4,4'-quinoline)-2',3'-dione