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A facile and efficient copper(I)-catalyzed one-pot, three-component diastereoselective synthesis that provides new 3-spiroazetidinimine-2-oxindoles in excellent yield has been accomplished. The 3-spiroazetidinimine-2-oxindoles underwent a facile ring-opening reaction of the spiroazetidinimine unit by treatment with KOH/MeOH and p-thiocresol under basic conditions to afford two new classes of fluorescent conjugated indolones. This method has general applications with regard to the imines that are derived from 9-fluorenone, 1,2-diketones, and 1,2,3-triketones. [ABSTRACT FROM AUTHOR]

Abstract: Palladium catalyzed synthesis of a number of novel 3-spirocyclopentene-2-oxindoles in good yields has been accomplished from geometrically strained 3-vinylcyclopropane-2-oxindole via vinylcyclopropane–cyclopentene rearrangement. [Copyright &y& Elsevier]

Abstract: Unusual reactivity of 1-aminoanthraquinone with a number of isatins and aryl alkynes in a copper catalyzed multicomponent reaction afforded a novel, highly conjugated, and separable regioisomers of 3-spiroheterocyclic 2-oxindoles in excellent combined yield. Both the regioisomers exhibited considerable optical properties and found as fluorescence materials. Based on experimental observation, a plausible reaction mechanism has been proposed. [Copyright &y& Elsevier]

Synthesis of highly functionalized allene appended oxindole derivatives from vinyl propargyl ether derivatives of Morita-Baylis-Hillman adducts of isatin via Claisen rearrangement has been achieved. Synthetic utility of the allene derivatives obtained has been demonstrated with the synthesis of methyl 2,5-dihydro-5-methyl-2-(1-methyl-2-oxoindolin-3-ylidene)furan-3-carboxylates in a one-pot cyclization reaction under basic conditions. A plausible mechanism of the reaction is presented. [ABSTRACT FROM AUTHOR]

The tert-hydroxyl protection in Morita-Baylis-Hillman (MBH) adducts of isatin using the system acyl halogenide/potassium carbonate is studied. [ABSTRACT FROM AUTHOR]

[Display omitted] • 7-Azaindole scaffolds are privileged bioactive compounds. • AMY undergoes cycloadditions to afford a range of bioactive heterocycles. • Synthesis of spiro pyrrolidines and Spiro pyrrolizidines products were achieved. • New products have two quaternary spiro carbons and two stereogenic centers. • Plausible mechanisms of the reactions have been provided. • Characterization of products, including XRD, are described. 32 AY CA reactions of 3-alkylidene-7-aza-2-indalone with acyclic and cyclic AY's generated in situ from 7-azaisatin/isatin and sarcosine/proline in the presence of Montmorillonite k 10 clay afforded highly functionalized 3, 3′-dispiropyrrolidine- and 3,3′-dispiropyrrolizidine bis 7-aza and 2-oxindole in excellent yield. The structure of the representative cycloadducts was established by single-crystal XRD. A plausible reaction mechanism is provided. Significantly the final product forms with newly formed two quaternary spiro carbons and two stereogenic centers simultaneously. [ABSTRACT FROM AUTHOR]

Abstract: The Morita–Baylis–Hillman adducts derived from isatins and maleimides have undergone a facile and efficient allylic nucleophilic substitution reaction with X, S, N, and O-nucleophiles to afford functionalized tetrasubstituted alkene appended oxindoles in very good yield. The MBH adducts and their acetates on treatment with halides, saturated and unsaturated amines, thiols, and trialkyl orthoformates afforded allyl halide, allyl amine, allyl thio-ether and allyl ether derivatives of oxindole, respectively. [Copyright &y& Elsevier]