title: Solution-phase synthesis of a diverse isocoumarin library.
abstract: The solution-phase synthesis of a 167-member library of isocoumarins is described. The key intermediates for library generation, 4-iodoisocoumarins, are easily prepared by iodocyclization of the corresponding 2-(1-alkynyl)arenecarboxylate esters. The 4-iodoisocoumarins undergo palladium-catalyzed Sonogashira, Suzuki-Miyura, and Heck reactions to yield a diverse set of isocoumarins. Alternatively, isocoumarins, bearing hydroxyl or bromine functionalities, have been prepared by ZnCl(2)- and Pd(PPh(3))(4)-mediated cyclization of the corresponding o-iodobenzoic acid and appropriate terminal alkynes. The resulting isocoumarins were further diversified by derivatization of the hydroxyl or bromine groups. A small set of isoquinolinones were also prepared from the corresponding isocoumarins.
authors.affiliation: Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
authors.forename: Sujata
authors.initials: S
authors.lastname: Roy
authors.forename: Sudipta
authors.initials: S
authors.lastname: Roy
authors.forename: Benjamin
authors.initials: B
authors.lastname: Neuenswander
authors.forename: David
authors.initials: D
authors.lastname: Hill
authors.forename: Richard C
authors.initials: RC
authors.lastname: Larock
mesh_terms: D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D049934:Isocoumarins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D054852:Small Molecule Libraries; D012996:Solutions; D013237:Stereoisomerism
chemical_list: D049934:Isocoumarins; D054852:Small Molecule Libraries; D012996:Solutions