119771-51-6

Basic information

• Product Name: 2-amino-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile
• Synonyms: 2-amino-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile
• CAS NO: 119771-51-6
• Molecular Formula: C19H17N3O3
• Molecular Weight: 335.35658
• Mol File: 119771-51-6.mol
• Article Data: 108

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-amino-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile(119771-51-6)
• EPA Substance Registry System: 2-amino-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile(119771-51-6)

Safety Data

• Hazardous Substances Data: 119771-51-6(Hazardous Substances Data)

Upstream product

• 151-18-8 2-cyanoethylamine 
• 91-56-5 indole-2,3-dione 
• 126-81-8 dimedone 
• 3471-13-4 dimedone 
• 109-77-3 malononitrile 
• 105-56-6 ethyl 2-cyanoacetate 
• 6532-16-7 1-(4-morpholinylmethyl)-1H-indole-2,3-dione 
• 6623-89-8 2-oxo-2,3-dihydroindolylidenemalononitrile 

Relevant articles and documents

Ammonium salt catalyzed multicomponent transformation: simple route to functionalized spirochromenes and spiroacridines

The combination of isatin or acenaphthoquinone, an activated methylene reagent, and 1,3-dicarbonyl compounds in the presence of catalytic ammonium chloride was found to be a suitable and efficient method for the synthesis of the biologically important spirooxindoles.

Synthesis of mono- and bis-spiro-2-amino-4H-pyrans catalyzed by S-alkyl O-hydrogen sulfothioate functionalized silica-coated magnetic nanoparticles under ultrasound irradiation

New S-alkyl O-hydrogen sulfothioate functionalized silica-coated magnetic nanoparticles were prepared in a simple method and evaluated as an efficient catalyst in synthesis of mono- and bis-spiro-2-amino-4H-pyrans through three or pseudo-five component re

An efficient one-pot multi-component synthesis of spirooxindoles using Fe3O4/g-C3N4 nanocomposite as a green and reusable catalyst in aqueous media

In this study, an efficacious method is described for the synthesis of spirooxindole derivatives using Fe3O4/g-C3N4 as a green catalyst. This is a one-pot three-component condensation in water as a clean and environmentally favorable media. The present procedure proposes various remarkable privileges such as mild reaction conditions, simple work-up procedure and environment friendly. Moreover, the catalyst used is easily recovered by the external magnetic field and reused without significant deterioration in catalytic activity after at least six times.

An efficiently and quickly synthesized NiO@g-C3N4 nanocomposite-catalyzed green synthesis of spirooxindole derivatives

NiO@g-C3N4 as an efficient catalyst for the synthesis of spirooxindole derivatives was prepared by impregnation of g-C3N4 with NiO nanoparticles and characterized by various techniques including thermogravimetri

Sulfonated chitosan encapsulated magnetically Fe3O4 nanoparticles as effective and reusable catalyst for ultrasound-promoted rapid, three-component synthesis of spiro-4H-pyrans

Abstract: A facile one-pot protocol for synthesis of spiro-4H-pyrans using sulfonated chitosan-coated Fe3O4 nanoparticles (Fe3O4@CS-SO3H NPs) as an efficient catalyst under ultrasonic condition has been developed. First, the Fe3O4@CS NPs were prepared from the reaction of chitosan with Fe3O4 NPs. Then, the treatment of Fe3O4@CS NPs with chlorosulfonic acid leads to the formation of Fe3O4@CS-SO3H NPs which exerts excellent catalytic activity toward one-pot, three-component synthesis of spiro-4H-pyran derivatives. The core–shell structure and the composition of produced magnetic nanocatalyst were characterized by FT-IR, XRD, VSM, SEM and EDX techniques. Graphical Abstract: [Figure not available: see fulltext.].

An efficient, room temperature, oxygen radical anion (O2?-) mediated, one-pot, and multicomponent synthesis of spirooxindoles

The present report highlights an efficient use of oxygen radical anion to promote a room temperature multi-component synthesis of spirooxindoles (4a-4l) under mild reaction conditions. The potassium superoxide (KO2) and tetraethylammonium bromide (TEAB) combination generate the oxygen radical anion in situ to promote this transformation. This method offers a sustainable and direct access to the biologically important spirooxindole derivatives in good to excellent yields.

A green synthesis of spirooxindole derivatives catalyzed by SiO2@g-C3N4 nanocomposite

In this study, SiO2 nanoparticles were immobilized onto the surface of g-C3N4 nanosheets. The characterization of SiO2@g-C3N4 nanocomposite has been done by Fourier transform infrared spect

Sodium stearate-catalyzed multicomponent reactions for efficient synthesis of spirooxindoles in aqueous micellar media

A new type of Lewis base-surfactant-combined catalyst (LBSC), sodium stearate, was applied as a catalyst in three-component one-pot reaction involving isatin, malononitrile, and 1,3-dicarbonyl compounds to afford the corresponding spirooxindoles derivativ

Synthesis, characterization, and application of CoFe2O4@amino-2-naphthol-4-sulfonic acid as a novel and reusable catalyst for the synthesis of spirochromene derivatives

In the present work, 1-amino-2-naphthol-4-sulfonic acid immobilized on functionalized CoFe2O4 nanoparticles was successfully synthesized as a new, efficient, and recoverable catalyst and tested for the synthesis of spirochromene derivatives by a simple, green, and inexpensive procedure. This magnetically heterogeneous nanocatalyst was characterized by various techniques such as Fourier transform infrared (FT-IR), thermal gravimetric analysis (TGA)/derivative thermogravimetric (DTG), X-ray diffraction (XRD), MAP, transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDS), vibrating sample magnetometer (VSM), Brunauer–Emmett–Teller (BET), and scanning electron microscopy (SEM) analyses. The novel synthesized nanocatalyst can be easily separated and can also be reused several times without appreciable loss in its catalytic activity. Furthermore, in comparison with previous reports, this nanocatalyst showed high thermal stability and acidic properties.

A practical green approach to diversified spirochromene/spiropyran scaffolds via a glucose-water synergy driven organocatalytic system

The development of a versatile, new biomimetic glucose-water organocatalytic system promoted, one-pot green and practical method for the synthesis of diversified spirochromenes/spiropyrans is reported. To the best of our knowledge this is the first report

Polyethylene glycol in water: Simple, efficient, and catalyst-free synthesis of 4H-pyran derivatives

A green, one-pot, multicomponent method for the synthesis of diverse library of 4H-pyran derivatives such as 4-phenyl-4H-pyrans, spirochromenes, and dihydropyrano[3,2-c]chromines was developed using polyethylene glycol (PEG-600) as promoting reaction medi

Oxalic acid dihydrate: Proline as a new recyclable designer solvent: A sustainable, green avenue for the synthesis of spirooxindole

The quest to develop an environmentally friendly, sustainable protocol for immensely bioactive spirooxindole derivatives has encouraged to explore oxalic acid dihydrate: proline low transition temperature mixture as a new designer solvent for the said syn

Microwave-assisted aqueous multicomponent reaction: Facile synthesis of polyfunctionalized indoline-spiro fused pyran derivatives

A green and highly efficient method for the synthesis of polyfunctionalized indoline-spiro fused pyran derivatives has been established. This reaction was conducted by reacting readily available and inexpensive starting materials, such as isatins, cyclic-1,3-dicarbonyl compounds, and malononitrile in aqueous media without any catalysts under microwave irradiation. The present green synthesis shows fascinating properties such as the use of water as the reaction solution, concise one-pot conditions, short reaction periods (8-14 min), and easy purifications. The synthesis could also set a good example to GAP (Group-Assistant-Purification) chemistry in which purification via chromatography can be avoided and the pure products can be easily acquired only by washing the crude products with 95% EtOH.

Efficient and convenient Polyethylene Glycol (PEG)-mediated synthesis of spiro-oxindoles

Polyethylene glycol (PEG) has been reported as an efficient and convenient medium for the three-component synthesis for spiro-oxindole.

An efficient protocol for multicomponent synthesis of spirooxindoles employing L-proline as catalyst at room temperature

An efficient three-component one-pot synthesis of medicinally important spirooxindoles is described by the reaction of isatin, malononitrile/ethyl cyanoacetate, and dimedone/barbituric acid using L-proline as catalyst in ethanol at room temperature. This approach is convenient, mild, and affords the products in high yields without the use of chromatography.

One-pot three-component synthesis of spirooxindoles catalyzed by hexamethylenetetramine in water

A simple, convenient, and multicomponent strategy for synthesis of spirooxindole derivatives has been developed. This strategy provides a rapid access to construct a diversity-oriented library of spirooxindoles by using three simple and readily available isatin, malononitrile or cyanoacetic ester, and 1,3-dicarbonyl compound catalyzed by hexamethylenetetramine in water.

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.

Sulfuric acid-modified poly(ethylene glycol): An efficient, biodegradable, and reusable polymeric catalyst for synthesis of spiro oxindole derivatives in aqueous medium

A versatile, novel, and environmentally benign strategy has been successfully developed for synthesis of oxindoles, an important class of potentially bioactive compounds. Sulfonated poly(ethylene glycol) was used as inexpensive and recyclable acidic catal

Synthesis and characterization of Co (III) salen complex immobilized on cobalt ferrite-silica nanoparticle and their application in the synthesis of spirooxindoles

The preparation, characterization and catalytic application of Co (III) salen complex loaded on cobalt ferrite-silica nanoparticle [CoFe2O4@SiO2@ Co (III) salen complex] are described. Co (III) salen complex loaded on ferr

Multi-component supramolecular synthesis of spirooxindoles catalyzed byβ -cyclodextrin in water

A neutral and efficient one-pot three-component aqueous-phase synthesis is developed for various spirooxindole derivatives from isatin, malononitrile, and 1,3-dicarbonyl compounds in high yields by supramolecular catalysis involving β-cyclodextrin. The β-

Na2EDTA: an efficient, green and reusable catalyst for the synthesis of biologically important spirooxindoles, spiroacenaphthylenes and spiro-2-amino-4H-pyrans under solvent-free conditions

For the first time, the organic salt Na2EDTA was used as a catalyst for an effective and facile preparation of spiro-4H-pyrans via single-pot three-component condensation of isatin/acenaphthoquinone/ninhydrin, malononitrile, and CH-acids throug

Guanine base stabilized on the magnetic nanoparticles as recyclable catalyst “on water” for the synthesis of spirooxindole derivatives

Guanine stabilized on the surface of silica-modified magnetic nanoparticles, by the propyl group as a linker, (Fe3O4@SiO2-n-(propyl)-guanine), was prepared, identified and used as a recyclable base in the synthesis of novel spirooxindole compounds and highly substituted dihydro-2-oxopyrroles in aqueous media. Fe3O4@SiO2-n-(propyl)-guanine was characterized via some spectroscopic and microscopic techniques such as Infrared spectroscopy (IR), X-ray diffraction spectroscopy (XRD), Energy dispersive X-ray spectroscopy (EDX), Vibrating sample magnetometry (VSM), Scanning electron microscopy (SEM), High resolution transmission electron microscopy (HR-TEM), Thermo-gravimetric analysis (TGA) and NMR-detected hydrogen/deuterium (H/D) exchange technique. The synthesized nanocomposite was employed as a new base catalyst for the synthesis of some novel spirooxindole compounds and highly substituted dihydro-2-oxopyrroles in aqueous media with good to excellent yields. This heterogeneous base catalyst could be recycled and reused up to ten times without appreciable loss of activity.

A green one-pot three-component synthesis of spirooxindoles under conventional heating conditions or microwave irradiation by using Fe3O4@SiO2-imid-PMAn magnetic porous nanospheres as a recyclable catalyst

An efficient, green and environmentally procedure for the synthesis of spirooxindole derivatives has been developed by a one-pot three-component reaction of isatin derivatives, activated methylene, and 1,3-dicarbonyl compounds in the presence of Fe3

Convenient synthesis of spirooxindoles using SnO2 nanoparticles as effective reusable catalyst at room temperature and study of their in vitro antimicrobial activity

New highly efficient method for safe, green and facile synthesis of spirooxindole derivatives have been presented. SnO2 nanoparticles (SnO2 NPs) as effective catalyst were synthesized through chemical precipitation method and charact

Protic guanidinium ionic liquid as a green and highly efficient catalyst for the synthesis of functionalized spirochromenes under solvent-free conditions

A simple and efficient method for the synthesis of functionalized spirochromenes is explained using protic guanidinium ionic liquid as a catalyst under solvent-free conditions at room temperature. This procedure is simple, clean, and excellent yields are

Environmentally friendly synthesis of Ag/SiO2 nanoparticles using Thymus kotschyanus extract and its application as a green catalyst for synthesis of spirooxindoles

Today, plant extracts based on synthetic procedures have drawn consideration over conventional methods like physical and chemical procedures to synthesize nanomaterials. Green synthesis of nanomaterials has become an area of interest because of numerous advantages such as non-hazardous, economical, and feasible methods with a variety of applications in biomedicine, nanotechnology and nano-optoelectronics and as catalysts for various organic transformations. In this research, silver nanoparticles were deposited on the surface of nano-silica spheres by an in-situ reduction of Ag+ ions using an aqueous extract of Thymus kotschyanus aerial parts as a natural reducing and a capping agent. The result recorded from ultraviolet–visible (UV–Vis) spectrometer, Fourier transform infrared spectroscopy (FT-IR), thermal gravimetric analysis, scanning electron microscopy with energy-dispersive X-ray spectroscopy (SEM–EDS) and X-ray powder diffraction supports the biosynthesis and characterization of Ag/SiO2 nanoparticles. The results indicated that the average size of Ag/SiO2 nanoparticles is 25–60?nm. The Ag/SiO2 nanoparticles act as an environmentally friendly heterogeneous catalyst in the synthesis of spirooxindoles via the three-component condensation reaction of isatins, activated methylene reagents, and 1,3-dicarbonyl compounds in aqueous media, and the desired products were obtained with yields ranging from 90 to 98%. The catalyst can be recovered easily and used repetitively without significant loss of catalytic activity. Graphical abstract: [Figure not available: see fulltext.].

Green synthesis and antibacterial, antifungal activities of 4H-pyran, tetrahydro-4H-chromenes and spiro2-oxindole derivatives by highly efficient Fe3O4@SiO2@NH2@Pd(OCOCH3)2 nanocatalyst

An efficiently, magnetically retrievable Fe3O4@SiO2@NH2@Pd(OCOCH3)2 nanoparticles was successfully synthesized and affirmed by several physicochemical characterization tools, such as scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-disoersive X-ray spectroscopy (EDX), Fourier-transform infrared spectroscopy (FT-IR), and power X-ray diffraction. Thereafter, the catalytic performance of this environmentally benign nanocatalyst was investigated in the one-pot multicomponent synthesis of biologically important 2-amino-3-cyano-4H-pyran, tetrahydro-4H-chromenes and spiro2-oxindole derivatives. The reaction was simply achieved via one-pot three-component reaction of arylaldehydes, malononitrile and dimedone/isatins/methylaceto acetate ethanol at room temperature, with excellent yields and high purity. A new catalytic system, recyclability of reaction medium, little reaction times and excellent yields with easy workup render this protocol more attractive and economically viable.