Regioselective synthesis of N-aminoisoindolones and mono-N- and di-N,N'-substituted phthalazones utilizing hydrazine nucleophiles in a palladium-catalyzed three-component cascade process.
A palladium-catalyzed three-component cascade process for the synthesis of isoindolone and phthalazone derivatives is reported. The cascade process involves carbonylation of an aryl iodide/Michael acceptor to give an acylpalladium species which is intercepted by a hydrazine nucleophile. Intramolecular Michael addition follows to give either N-aminoisoindolones or mono- N- and di-N,N'-phthalazones depending on whether a monosubstituted or 1,2-disubstituted hydrazine nucleophile is used.
Molecular Innovation Diversity and Automated Synthesis Centre, School of Chemistry, University of Leeds, Leeds LS2 9JT, UK. r.grigg@leeds.ac.uk.
Ronald
R
Grigg
Visuvanathar
V
Sridharan
Mufakhrul
M
Shah
Simon
S
Mutton
Colin
C
Kilner
David
D
MacPherson
Peter
P
Milner
D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry*; D054833:Isoindoles / Q000138:chemical synthesis*; D010165:Palladium; D010793:Phthalazines / Q000138:chemical synthesis*
D006834:Hydrazines; C110621:Isoindol-1-one; D054833:Isoindoles; D010793:Phthalazines; C029424:hydrazine; D010165:Palladium