Expanding the chemical diversity of spirooxindoles via alkylative pyridine dearomatization
نویسندگان
چکیده
A mild and practical synthesis of spirooxindole [1,3]oxazino derivatives from N-substituted isatins and 1,3-dicarbonyl compounds with pyridine derivatives is reported. The reactions provided good to excellent yields. Further exploration of the molecular diversity of these compounds is demonstrated through Diels-Alder reactions.
منابع مشابه
Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration
The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization-cyclization followed by C3- to C2-alkyl migration and rearomatization.
متن کاملH6P2W18O62: A Green and Reusable Catalyst for the One-pot Three-Component Synthesis of Spirooxindoles in Water
Wells–Dawson tungsten heteropolyacid (H6P2W18O62) has been applied as an effective heterogeneous catalyst for one-pot synthesis of spiro[4H-pyran-3,3’-oxindoles] via reaction of various isatins, malonitrile and 1,3-dicarbonyl compound in water. The corresponding products were obtained in high yields. The catalysts were easily recycled and reused without loss of their catalytic activity.
متن کاملAn enantioselective organocatalytic oxidative dearomatization strategy.
The inherent reactivity and functionality stored within aromatic systems provide numerous possibilities for the synthesis of 3-D organic structures via dearomatization processes.1,2 Under oxidizing conditions, the dearomatization of orthoand para-substituted phenols forms cyclohexadienones,3 and these products have found widespread use in the chemical synthesis of natural products.4 Additionall...
متن کاملMetal-ligand cooperation by aromatization-dearomatization as a tool in single bond activation.
Metal-ligand cooperation (MLC) plays an important role in bond activation processes, enabling many chemical and biological catalytic reactions. A recent new mode of activation of chemical bonds involves ligand aromatization-dearomatization processes in pyridine-based pincer complexes in which chemical bonds are broken reversibly across the metal centre and the pincer-ligand arm, leading to new ...
متن کاملPd(0)-catalyzed chemoselective construction of spirocarbocycles via an alkyne insertion/β-naphthol dearomatization cascade.
A microwave-assisted Pd(0)-catalyzed alkyne migratory insertion/β-naphthol dearomatization cascade process has been accomplished to access a variety of spirocyclic compounds bearing all-carbon quaternary stereogenic centers in high yields with excellent chemoselectivities.
متن کامل