59762-59-3

Upstream product

• 1217-89-6 1-benzylisatin 
• 109-77-3 malononitrile 
• 91-56-5 indole-2,3-dione 
• 100-39-0 benzyl bromide 
• 92552-73-3 1-benzyl-3-hydroxyindolin-2-one 
• 7135-32-2 1-benzylindolin-2-one 
• 620-05-3 iodomethylbenzene 

Downstream Products

• 933850-37-4 2?amino?1'?benzyl?2',5?dioxo?1',2',5,6,7,8?hexahydrospiro[chromene?4,3'?indole]?3?carbonitrile 
• 625367-49-9 C₂₇H₂₁N₅O 
• 1234379-45-3 (R)-ethyl 2′-amino-1-benzyl-3′-cyano-6′-methyl-2-oxospiro[indoline-3,4′-pyran]-5′-carboxylate 
• 1234379-40-8 C₂₃H₁₉N₃O₃ 

Relevant academic research and scientific papers

Bifunctional Squaramide-Catalyzed Asymmetric [3 + 2] Cyclization of 2-(1-Methyl-2-oxoindolin-3-yl)malononitriles with Unsaturated Pyrazolones to Construct Spirooxindole-Fused Spiropyrazolones

The present paper reports a highly stereoselective synthesis of spirooxindole-fused spiropyrazolones through the asymmetric [3 + 2] cyclization reaction of 2-(1-methyl-2-oxoindolin-3-yl)malononitriles with unsaturated pyrazolones under mild conditions. Wi

A One-Pot, Multicomponent Synthesis of 5′-Amino-2,2′-dioxospiro[indoline-3,3′-pyrrole]-4′-carbonitriles

A novel, one-pot, multicomponent synthesis of 5′-amino-2,2′-dioxospiro[indoline-3,3′-pyrrole]-4′-carbonitriles is described. The Knoevenagel condensation reaction between isatin derivatives and malononitrile gave the corresponding cyclic arylmethylidenema

'On water' Knoevenagel condensation of isatins with malononitrile

Grinding of isatins with malononitrile in the presence of 1-5 equiv. of water for 15 min at room temperature affords the corresponding (2-oxo-1,2-dihydro-3H-indol-3-ylidene)malononitriles, the Knoevenagel condensation products, in 89-99% yields.

Chiral naphthyl-C2-indole as scaffold for phosphine organocatalysis: Application in asymmetric formal [4 + 2] cycloaddition reactions

The applications of a newly designed chiral naphthyl-C2-indole bifunctional phosphine organocatalyst in stereoselective formal [4 + 2] cycloaddition reactions were reported. The chiral naphthyl-C2-indole skeleton was introduced to bifunctional phosphine o

Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon-carbon double bond formation

The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)-H/C(sp3)-H bonds to afford olefins by 4H elimination is described. This method employs air (molecular oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations suggest that the present transformation involves a radical process.

Iron-catalyzed one-pot oxidation/Knoevenagel condensation reaction using air as an oxidant

A green and highly efficient iron-catalyzed one-pot oxidation/Knoevenagel tandem reaction for the synthesis of α, β-unsaturated nitriles from secondary alcohols and malononitrile has been achieved. The reaction performed under mild conditions with air as

Design, synthesis and evaluation of structurally diverse chrysin-chromene-spirooxindole hybrids as anticancer agents

A series of structurally diverse chrysin-chromene-spirooxindole hybrids were designed, synthesized via a Knoevenagel/Michael/cyclization of chrysin and isatylidene malononitrile derivatives through utilizing a hybrid pharmacophore approach. The newly synthesized compounds were evaluated for their in vitro anticancer activity, and most of the compounds showed stronger anti-proliferative activity than parent compound chrysin. In particular, compound 3e had the highest cytotoxicity towards A549 cells (IC50 = 3.15 ± 0.51 μM), and had better selectivity in A549 cells and normal MRC-5 cells. Furthermore, compound 3e could significantly inhibit the proliferation and migration of A549 cells in a dose-dependent manner, as well as induce the apoptosis possibly through mitochondria-mediated caspase-3/8/9 activation and multi-target co-regulation of the p53 signaling pathway. Thus, our results provide in vitro evidence that compound 3e may be a potential candidate for the development of new anti-tumour drugs.

Enantioselective Construction of Tetrahydroquinolin-5-one-Based Spirooxindole Scaffold via an Organocatalytic Asymmetric Multicomponent [3 + 3] Cyclization

The first catalytic enantioselective construction of biologically important tetrahydroquinolin-5-one-based spirooxindole has been developed via a chiral cinchona alkaloid catalyzed asymmetric three-component [3 + 3] cyclization of cyclic enaminone, isatin

[bmim]OH: An efficient catalyst for the synthesis of mono and bis spirooxindole derivatives in ethanol at room temperature

A rapid and efficient, one pot synthesis of spirooxindole derivatives has been attempted by three-component reaction of isatin, malononitrile and carbonyl compound possessing a reactive α-methylene group by using task specific ionic liquid, 1-butyl-3-meth

Molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael addition reaction: Efficient and mild conditions for the synthesis of 3,3-disubstituted oxindoles with an all carbon quaternary center

A one-pot, molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael addition reaction has been developed. We discovered that the molecular sieves not only promoted the Knoevenagel condensation of isatins and malononitrile to generate isatylidene malononitriles, but also promoted the later decarboxylative Michael addition reactions of β-ketoacids and malonic acid half thioesters (MAHTs) with isatylidene malononitriles. This protocol provides a mild and efficient method for the preparation of 3,3-disubstituted oxindoles with an all carbon quaternary center in high yields.