A novel cyclization reaction of ethenetricarboxylate derivative aromatic compounds in the presence of various Lewis acids gave benzo-annulated cyclic compounds such as oxindole and benzofuran derivatives via Friedel-Crafts intramolecular Michael addition in high yields. For example, the reaction of diethyl 2-[(N-methyl-N-phenylcarbamoyl)methylene]malonate (1a) in the presence of ZnCl2 at room t...

In the title compound, C19H14N2O5, the spiro junction links an oxindole moeity and a furan ring, which subtend a dihedral angle of 83.49 (6)°. The mol-ecular structure features an N-H⋯O hydrogen bond, which generates an S(6) ring motif. The crystal packing is governed by two N-H⋯O inter-actions, one of which generates a centrosymmetric R 2 (2)(14) dimer. The other N-H⋯O inter-action along with ...

An enantioselective α-oxyamination of unprotected 3-substituted oxindoles with nitrosobenzene catalyzed by tertiary amine-thiourea bifunctional organocatalysts has been developed and affords the corresponding 3-amino-2-oxindole derivatives in good yields and with moderate to excellent enantioselectivities (up to > 99.9 : 0.1 er when the product is isolated by direct filtration from the reaction...

The title spiro-oxindole compound, C(26)H(23)N(3)O(3), was prepared by the reaction of isatin, 3-methyl-1-phenyl-2-pyrazolin-5-one and 5,5-dimethyl-cyclo-hexane-1,3-dione in an ethanol solution. The fused cyclo-hexene ring adopts an envelope conformation. The dihedral angle between the aromatic and pyrazoline rings is 23.70 (8)°. An intra-molecular C-H⋯O inter-action occurs. The crystal structu...

In the title compound, C(30)H(30)N(4)O(7)S, the two spiro junctions link a planar 2-oxindole ring [with a mean deviation from the plane of 0.0319 (3) Å, a pyrrolidine ring in an envelope conformation and a thia-zolo[3,2-a]pyrimidine system. Two mol-ecules are connected into a dimer by two N-H⋯O hydrogen bonds, forming an R(2) (2)(8) graph-set motif. The title compound has four stereogenic cente...

Multicomponent reactions (MCRs) are a valuable tool in diversity-oriented synthesis. Its application to privileged structures is gaining relevance the fields of organic and medicinal chemistry. Isatin, due its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole-derivatives (including spirooxindoles, bis-oxindoles 3,3-disubstituted oxindoles) ...

MDM2 oncoprotein binds directly to the p53 tumor suppressor and inhibits its function in cancers retaining wild-type p53. Blocking this interaction using small molecules is a promising approach to reactivate p53 function and is being pursued as a new anticancer strategy. The spiro-oxindole MI-43, a small-molecule inhibitor of the MDM2-p53 interaction, was designed and examined for its cellular ...