title: Synthesis and reactivity of furoquinolines bearing an external methylene-bond: access to reduced and spirocyclic structures.
abstract: A family of furoquinolines were efficiently obtained through a tandem acetalization/cycloisomerization process catalyzed by (5 mol%) silver imidazolate polymer and triphenylphosphine, and diversity was brought by the use of 7 different alcohol groups. From these furoquinolines, 3 examples of reduced derivatives could be obtained (d.r. up to 94 : 6), 10 different spiroketal derivatives by hetero-Diels-Alder reaction (d.r. up to 20 : 1), 8 hetero-[5,5]-spirocycles by cycloaddition with dibromoformaldoxime (d.r. up to 86 : 14) and finally 6 hetero-[5,6]-spirocycles by [4 + 2] cycloaddition with ethyl 3-bromo-2-(hydroxyimino)propanoate (d.r. up to 90 : 10).
authors.affiliation: Institut Curie and CNRS, UMR 176 CSVB, 26 rue d'Ulm, 75248, Paris cedex 05, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Bantreil
authors.forename: Carine
authors.initials: C
authors.lastname: Vaxelaire
authors.forename: Thomas
authors.initials: T
authors.lastname: Godet
authors.forename: Evelyne
authors.initials: E
authors.lastname: Parker
authors.forename: Carole
authors.initials: C
authors.lastname: Sauer
authors.forename: Philippe
authors.initials: P
authors.lastname: Belmont
mesh_terms: D003500:Cyclization; D008697:Methane / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D015363:Quinolones / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*
chemical_list: D015363:Quinolones; D013141:Spiro Compounds; D008697:Methane