Branch-selective synthesis of oxindole and indene scaffolds: transition metal-controlled intramolecular aryl amidation leading to c3 reverse-prenylated oxindoles.
In an effort to access biologically important scaffolds, a concise branch-selective synthesis of C3 tertiary oxindoles by Cu(I)-catalyzed aryl amidation and 2,2-dimethyl indene by Pd(0)-catalyzed Heck cyclization has been accomplished from acyclic reverse-prenylated intermediates. Oxindole C3-enolate generation using NaH followed by alkylation in the presence of appropriate electrophiles provides a novel route to quaternary C3 reverse-prenylated oxindoles.
Ignatenko
Vasily A
VA
Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA.
Deligonul
Nihal
N
Viswanathan
Rajesh
R
D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D054876:Prenylation
D007192:Indenes; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D003300:Copper