ABSTRACT
A convergent total synthesis of MK-801 has been achieved. Key synthetic transformations include a multicomponent Barbier-type reaction to construct the α-branched amine, a selective Heck α-coupling tactic to generate the exocyclic alkene skeleton, and a late-stage intramolecular hydroamination reaction between the exocyclic alkene and the secondary protected amine. The efficacy of this method was demonstrated by the synthesis of two news analogues substituted on the aromatic rings.
Subject(s)
Dizocilpine Maleate/chemical synthesis , Dizocilpine Maleate/chemistry , Molecular StructureABSTRACT
An intriguing conversion of 3-bromo-2H-coumarins to 3-(benzofuran-2-yl)-2H-coumarins under palladium catalysis is reported. The process involves, from only one single starting material, three transformations and two bond formations in one pot: C-C bond formation via C-H activation and C-O bond formation through 2H-coumarin-to-benzofuran ring contraction under palladium catalysis. Moreover, the photophysical properties of all synthesized compounds were studied.
ABSTRACT
An efficient Pd-catalyzed decarboxylative coupling of heterocyclic carboxylic acids with heterocyclic halides to achieve the synthesis of biheterocycles of biological interest has been reported. In all cases, the cross-coupling reactions take place rapidly in DMSO in good yields and efficiently proceed in the presence of a PdBr2/DPEphos catalytic system, furnishing the novel biheterocycles based on quinolin-4-one, quinolin-2-one, chromone, and coumarin scaffolds.
