Solution-phase synthesis of a diverse isocoumarin library.
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.
Roy
Sujata
S
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Roy
Sudipta
S
Neuenswander
Benjamin
B
Hill
David
D
Larock
Richard C
RC
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
D049934:Isocoumarins; D054852:Small Molecule Libraries; D012996:Solutions