Synthesis of fused 2′-amino-3′-R-spiro-[indole-3,4′-pyran]-2(1H)-ones

An efficient one‐pot three‐component reaction for synthesis of spirooxindole derivatives in water media under catalyst‐free condition

“…A literature survey reveals several multicomponent reactions (MCRs) procedures using InCl 3 5, triethylbenzylammonium chloride (TEBA) 6, tris(2–8 hydroxyethyl)amine 7, tetrabutylammonium fluoride (TBAF) 8, L ‐Proline 9, and ethylenediamine diacetate(EDDA) 10 as catalyst, as well as using electrocatalytic method 11 to prepare them. However, few attempts have been done on reducing prolonged reaction time, toxic solvents, and moderate yields of the product.…”

Molecular diversity of spirooxindoles. Synthesis and biological activity

“…The main synthetic method for assembling of spiro[4H -pyran-oxindole] compounds is based on the three-component reactions of two (usually different) 1,3-dicarbonyl compounds, or alternatively their synthetic equivalents, with isatin derivatives. We and others investigated three-component reactions of isatins 114, malononitrile 240, phenyl-acetonitrile 241, methyl-, ethyl-and other cyanoacetates 242, and various 1,3-dicarbonyl compounds 243 to afford a series of spiroindolones 244 (Scheme 66)[132][133][134][135][136].…”

Three-component condensation of ethyl 4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates with malononitrile and 5,5-dimethylcyclohexane-1,3-dione

“…We previously reported on three-component spiro heterocyclization of isatin with malononitrile and 5,5-dimethylcyclohexane-1,3-dione (dimedone), which led to the formation of 2′-aminospiro[indole-3,4′-pyran]-2(1H)-ones [1]. We now describe the three-component reaction of 1-substituted ethyl 4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates Ia and Ib with malononitrile and dimedone.…”