title: Synthesis of fluorenone and anthraquinone derivatives from aryl- and aroyl-substituted propiolates.
abstract: Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Diels-Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg , Hans-Meerwein-Str., 35043 Marburg, Germany.
authors.forename: Florian
authors.initials: F
authors.lastname: Pünner
authors.forename: Justin
authors.initials: J
authors.lastname: Schieven
authors.forename: Gerhard
authors.initials: G
authors.lastname: Hilt
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D061565:Cycloaddition Reaction; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D000880:Anthraquinones; D005449:Fluorenes; D007454:Iodides; D011422:Propionates; D017967:Zinc Compounds; C042834:9,10-anthraquinone; D003035:Cobalt; C029770:zinc iodide