313381-87-2

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 130817-33-3 2-(5-bromo-2-oxoindolin-3-ylidene)malononitrile 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 109-77-3 malononitrile 
• 126-81-8 dimedone 

Relevant academic research and scientific papers

Application of sulfonic acid functionalized SBA-15 as a new nanoporous acid catalyst in the green one-pot synthesis of spirooxindole-4H-pyrans

Sulfonic acid functionalized SBA-15 (SBA-Pr-SO3H) as a new nanoporous solid acid catalyst was applied in the green one-pot synthesis of spirooxindole-4H-pyrans via condensation of isatins, malononitrile or methyl cyanoacetate or ethyl cyanoacetate, and 4-hydroxycoumarin in water solvent. SBA-Pr-SO3H was proved to be an efficient heterogeneous nanoporous solid acid catalyst with a pore size of 6 nmthat could be easily handled and removed from the reaction mixture by simple filtration and can be recovered and reused for several times without any loss of activity. The significant merits of present methodology are its simplicity, short reaction time, good yields, and environmentally benign mild reaction condition as water was used as a green solvent.

Microwave promoted and improved thermal synthesis of spiro[indole- pyranobenzopyrans] and spiro[indole-pyranoimidazoles]

Spiro[indole-pyranoimidazoles] (5) and spiro[indole-pyranobenzopyrans] (6) are readily synthesized in one step in 86-92 and 91-97% yields by the Michael condensation of 3-dicyanomethylene-2H-indol-2-ones (2) with 1-phenyl-2- thiohydantoin (3) and 4-hydroxy-2H-1-benzopyran-2-one (4), respectively, without using any catalyst under different reaction conditions (conventional heating and microwave irradiation using (a) polar solvents (b) neutral alumina/silica gel as inorganic solid support in solvent free conditions). 2 was synthesized in situ by the Knoevenagel condensation of indole-2,3-dione (1) and malononitrile in the absence of any catalyst. 100% conversion was observed in most cases on TLC which also showed the formation of a single product. The comparison between the various methods is established.

Application of immobilized sulfonic acid on the cobalt ferrite magnetic nanocatalyst (CoFe2O4@SiO2@SO3H) in the synthesis of spirooxindoles

Sulfonic acid immobilized on the surface of magnetically cobalt ferrite/silicate is a green, convenient, efficient and recyclable catalyst which can be applied in organic reactions ranges from lab to industry goals as a solid acid to achieve high yield products. After synthesizing (CoFe2O4/SiO2/SO3H), it was also characterized by using different techniques such as FT-IR, XRD, EDX, VSM, TEM, SEM, TGA and so on which everyone approved presented structure. In this study, we are on to use this catalyst in a certain multicomponent reaction that is a common way to produce heterocycle compounds in order to synthesis spirooxindole derivatives which possess biological capabilities as anticancer and antimicrobial drugs. Hence, the three-component reaction of malononitrile, dimedone and isatin were performed in one pot under optimized situations of 80?°C temperature, reflux condition and water/ethanol (1:1) mixture as the solvent. Also, the present study shows unique advantages, such as simple synthesis of the catalyst, high magnetic properties, easy separation of catalyst with a permanent magnet, and the application of inexpensive and available precursors. At the end of the reaction, we gained the high yields of product at a short time that represents the high catalytic activity of the catalyst.

γ-Valerolactone as a Promising Bio-Compatible Media for One-Pot Synthesis of Spiro[indoline-3,4'-pyrano[3,2-c]chromene Derivatives

A general, highly efficient, and green protocol for the synthesis of biologically important spiro[indoline-3,4′-pyrano[3,2-c]chromene derivatives is developed by one-pot, three-component approach involving substituted isatin, active methylene group, and 4

An efficient approach for the synthesis of spirooxindole derivatives catalyzed by novel sulfated choline based heteropolyanion at room temperature

A new zwitterionic salt, sulfated choline based heteropolyanion, which was reported earlier by our group, has been found to be very effective for the synthesis of spirooxindole derivatives at room temperature. The heteropolyanion based on sulfated ionic liquid (HIL) showed promising features for the reaction, such as shorter reaction time, high product yields (about 90-95%), simple work up, easy removal, and reusability of the catalyst for several times without significant loss in its efficiency. This has made the protocol sustainable and economic.

Design and fabrication of novel polymerized dual nature ionic liquid as highly effective catalyst for regioselective synthesis of monospiro derivatives

Poly (ionic liquid)s (PILs) are promising candidates in catalytic transformations; however, hyper cross-linked poly ionic liquids have been rarely reported in catalysis field. In this study, we developed a novel hyper cross-linked PIL (HCPIL) as an effective heterogeneous catalyst for regioselective synthesis of monospiro compounds. For this purpose, a new polymerizable ionic liquid (1-(2-methacryloyloxy)ethyl)-3-vinylimidazolium bromide ([MEVIm]Br)) was designed and synthesized with two different natures; that is, ionic monomer and cross-linker agent. The successful construction of dual nature ionic liquid (IL) was confirmed by analytical techniques such as 1H NMR, 13C NMR, elemental, and FTIR. Next, magnetic HCPIL was fabricated using copolymerization of the prepared IL with N,N-methylenebisacrylamide (MBAA) in the presence of a water soluble initiator (4,4‘-azobis(4-cyanopentanoic acid)) supported on vinyl functionalized Co3O4 nanoparticles (NPs). The results illustrated that the polymerization of ILs and covalent binding onto the magnetic support improved the thermal stability (from 75 to 33% weight loss around 450 °C), reusability, catalytic activity, and generated porous structure. Accordingly, the proposed magnetic Co3O4@p[MEVIm]Br composite was investigated as a heterogeneous catalyst for the ultrasound-assisted synthesis of new and known spirooxindole-2-azapyrrolizidines and spiro-2-amino-4H-pyran-oxindoles; and it showed accelerated mass transfer owing to its great porosity, high surface area (170.0 m2/g), and abundant accessible active sites. The applied scalable catalytic protocol has integrated the rules of an ideal biology-oriented synthesis and organic synthesis to access a spiro heterocyclic skeleton. Easy work-up, high regioselectivity, excellent yields (>90%), short reaction time (6–12 min), and green reaction media are the other advantages of the proposed synthetic method.

CsF promoted rapid synthesis of spirooxindole-pyran annulated heterocycles at room temperature in ethanol

A newer, versatile, and straightforward synthetic strategy for the construction of functionalized spirooxindole-pyran annulated heterocycles is described. The procedure is based on CsF-promoted rapid tandem Knoevenagel-Michael-Cyclocondensation reaction o

Cu (II)-β-cyclodextrin complex stabilized on magnetic nanoparticles: A retrievable hybrid promoter for green synthesis of spiropyrans

The magnetic core of manganese ferrite (MnFe2O4) nanoparticles has a significant stability in comparison with ferrite (Fe3O4) nanoparticles. The unique supramolecular properties of β-cyclodextrin (β-CD), such as

Tris-hydroxymethylaminomethane (THAM): An efficient organocatalyst in diversity-oriented and environmentally benign synthesis of spirochromenes

Tris-hydroxymethylaminomethane has been demonstrated to be an efficient organocatalyst in diversity-oriented synthesis of medicinally prevalent spirochromenes by one-pot, three-component reactions between isatins, malononitrile, and enolizable C–H acids l

Synthesis of spiropyran derivatives over 1-(carboxymethyl) pyridinium iodide as nanostructured pyridinium salt under aqueous media

In this work, acetic acid functionalized pyridinium salt, namely 1-(carboxymethyl)pyridinium iodide {[cmpy]I}, has been applied as reusable nanostructured catalyst for green, simple and efficient preparation of spiropyrans by the one-pot domino Knoevenagel-Michael-cyclization reaction of isatin derivatives or acenaphthenquinone, with malononitrile, and 1,3-dicarbonyl compounds under aqueous media. Moreover, 1H and 13C NMR, mass, CHN analysis, Fourier transform infrared spectroscopy (FTIR), scanning electron microscope (SEM), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), X-ray diffraction analysis (XRD), and calculation of crystallite size and interplaner distance of the catalyst have been studied.