Condensation Of Isatin Research Articles

Synthesis, characterization and application of alumina/ vanadium pentoxide nanocomposit by sol–gel method

In this work, we report the preparation of Al2O3/V2O5 nanocomposit using vanadium and aluminum nitrate by sol–gel method. Characterization of nanocomposit was carried out by powder X‐ray diffractometry (XRD), Fourier transform infrared (FT‐IR), scanning electron microscopy (SEM), Energy‐Dispersive X‐ray (EDX) and UV spectroscopy. Then, applicability of the synthesized nanocomposit was tested as a nanocatalyst for the synthesis of diindolyl oxindole derivatives, an important class of potentially bioactive compounds. The products were obtained in good to high yields from one‐pot three‐component condensation of isatin with indole. Also, this nanocatalyst has been reused several times, without observable loss of activity.

Efficient four‐component synthesis of spiroindole derivatives catalysed by a versatile and reusable nano‐paramagnetic catalyst

A simple, efficient and environmentally benign route was developed for the preparation of spiro(indoline‐3,4‐pyrano[2,3‐c]pyrazole) derivatives with good yields from condensation of isatins, malononitrile (or ethyl cyanoacetate), hydrazine hydrate and ethyl acetoacetate catalysed by PFu@Fe3O4 nanocomposite. The use of easily available catalyst, shorter reaction times, better yields, simplicity of reaction, heterogeneous system and easy work‐up are the advantages of the method presented. Characterization of the catalyst was performed using Fourier transform infrared spectroscopy, X‐ray diffraction and transmission electron microscopy.

One-Pot Access to a Library of Dispiro Oxindole-pyrrolidine/pyrrolothiazole-thiochromane Hybrids via Three-Component 1,3-Dipolar Cycloaddition Reactions.

A library of novel dispiro compounds containing oxindole pyrrolidine/oxindolopyrrolothiazole-thiochroman-4-one hybrid frameworks has been synthesized in a fully regio- and stereoselective fashion by the three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the condensation of isatins and secondary amino acids (sarcosine/l-thioproline) with 3-arylidenethiochroman-4-ones. This experimentally simple protocol provides good yields of structurally complex, biologically relevant heterocycles in a single operation.

ChemInform Abstract: The Asymmetric Synthesis of CF3‐Containing Spiro[pyrrolidin‐3,2′‐oxindole] Through the Organocatalytic 1,3‐Dipolar Cycloaddition Reaction.

AbstractA series of unprecedented ketimines, obtained by condensation of isatins with trifluoroethylamine, is used in an asymmetric, organocatalyzed 1,3‐dipolar cycloaddition reaction providing trifluoromethylated spirooxindoles bearing four contiguous stereocenters.

ChemInform Abstract: Synthesis of Spirooxindole Pyrimidines Catalyzed by Silica‐Bonded N‐Propyltriethylenetetramine as a Recyclable Solid Base Catalyst in Aqueous Medium.

AbstractThe title compounds and related benzopyran derivatives are obtained by one‐pot three‐component condensation of isatin, activated methylene compounds, and barbituric acid or cyclohexanedione derivatives, respectively.

Synthesis of some new mixed azines, Schiff and Mannich bases of pharmaceutical interest related to isatin

Abstract The mixed azines 3a–h and 4 were obtained by treating 3-hydrazonoindolin-2-one (2) with the appropriate aldehyde or dialdehyde. Treatment of 3b or 3c with formaldehyde or glutaric dialdehyde and the appropriate amine afforded the azine Mannich bases 5–7. The condensation of isatin or its N-Mannich base 8 with 1-aminopiperidine, 4-aminomorpholine and 1,4-diaminopiperazine gave 10a–d, 12 and 13. The Mannich bases 14 and 15 were obtained from 10a and 10b. Treatment of 2 with succinic, phthalic and quinolinic anhydride and pyromellitic dianhydride afforded compounds 16, 17a, 17b and 18, respectively. The synthesis of isatin Schiff bases incorporating a benzoylpiperidine, benzoylmorpholine and 1,4-dibezoylpiperazine moiety and their N-Mannich bases was investigated.

Condensation of Indole with Isatin over AlCl<sub>3</sub>/Mesoporous Aluminosilicate

Aluminium chloride immobilized on mesoporous aluminosilicate was investigated as catalysts in the condensation of isatin with indole. AlCl3/mesoporous aluminosilicate (AlCl3/AM) catalysts were prepared by impregnation of 1, 5, 10 and 15 wt% AlCl3 on the surface of mesoporous aluminosilicate. A maximum conversion of isatin was achieved using 15% AlCl3/AM catalyst whereas the highest selectivity of 68.97% towards trisindoline was obtained using pure AM. The activity of the catalysts was depended on their acid site number and surface area. The number of Brønsted acid and the surface area affected to the conversion of isatin while the total acidity and the number of Lewis acid influenced the selectivity.

Efficient Green Approach for the Synthesis of Spiro[indoline-3,4′-pyrazolo[3,4-b]quinoline]diones Using [NMP]H2PO4 and Solvatochromic and pH Studies

A mild and efficient protocol for the synthesis of spiro[indoline-3,4′-pyrazolo[3,4-b]quinoline]diones via a one-pot, three-component condensation of isatins, 1,3-dicarbonyls, and 5-amino-1-phenyl-3-methylpyrazole using [NMP]H2PO4 as a catalyst in EtOH/H2O is described. The catalyst could be recycled and reused four times without significant loss of activity. Spiro[indoline-3,4′-pyrazolo[3,4-b]quinoline]diones with stabilized zwitter ionic resonance structures showed feasible application as new fluorescent probes and pH indicators. These chemosensors have a good wavelength shift and showed excellent sensitivity in the range of pH from 11 to 13.

SYNTHESIS AND BIOLOGICAL EVALUATION OF N-(SUBSTITUTED PHENYL)-2-(5H-[1,2,4]TRIAZINO[5,6-b]INDOL-3-YLSULFANYL)ACETAMIDES AS ANTIMICROBIAL, ANTIDEPRESSANT AND ANTICONVULSANT AGENTS.

A new series of N-Aryl-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides were synthesized by condensation of tricyclic compound 2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione with chloro N-phenylacetamides. The tricyclic compound was obtained by condensation of Isatin with thiosemicarbazide. Chloro N-phenylacetamides were obtained from different substituted anilines. Their structures were characterized by IR, 1H NMR, LC-MS and elemental analyses. Newly synthesized compounds were screened for antimicrobial, antidepressant and anticonvulsant activities. Preliminary results indicated that most of the compounds showed lesser MIC value than the standard drug used when tested for antimicrobial activity. Some of the compounds were endowed with very good antidepressant and anticonvulsant activity.

Co(II), Ni(II), Cu(II) and Zn(II) complexes of isatinyl‐2‐aminobenzoylhydrazone: synthesis, characterization and anticancer activity

This article describes the synthesis, structural aspects and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes of a new hydrazone derived from the condensation of isatin and 2‐aminobenzoylhydrazide. The ligand is well characterized using 1H NMR, 13C NMR, 2D HETCOR, mass and IR spectral studies. The chelating tendency of the ligand towards transition metal ions is established using analytical and spectral studies, which reveal the monobasic tridentate nature of the ligand. Octahedral geometry for Co(II), Cu(II) and Zn(II) and tetrahedral geometry for Ni(II) are tentatively proposed. All the synthesized compounds were screened for in vitro anticancer activity against Ehrlich ascites carcinoma and human cancer cell lines (adenocarcinoma HT29, kidney cancer cell line K293 and breast cancer cell line MDA231) using tryphan blue exclusion method and MTT assay. Copyright © 2014 John Wiley & Sons, Ltd.

Oxidative Ring Expansion of Spirocyclic Oxindole Derivatives

Oxidation of the spirocyclic oxindole derivative, isamic acid 1, led to decarboxylation and ring expansion to quinazolino[4,5-b]quinazoline-6,8-dione 7 rather than, as previously believed, its isomer 6. The structure of 7 was confirmed by X-ray crystallography. Condensation of isatin (indole-2,3-dione) and 2-aminobenzamide led to the spirocyclic molecule, spiro[3H-indole-3,2'(1H)quinazoline]-2,4'(1H,3H)dione 8, which was also identified as an intermediate in the oxidation of isamic acid. Mild hydrolysis of 7 gave the 10-membered molecule 22. Isamic acid could easily be converted to N-nitrosoisamic acid, which when heated in ethanol underwent a ring expansion to a hydroximino derivative, 38, of compound 6. The structure of 38 was confirmed by X-ray crystallography.

Synthesis and study of 3-methyl-6H-indolo[2,3-b]quinoxalines

By the condensation of isatin, N-methyl-, N-propyl-, N-benzoylisatin with 4-methyl-1,2-benzeneldiamine 3-methyl-6H-indolo[2,3-b]quinoxalines were obtained in high yields. The reaction occurs stereoselectively, in the mixture only one of possible isomers is present. By the oxidation of methyl group of the quinoxaline fragment new carbonyl derivatives were obtained, and by the reduction of nitro group, the corresponding indoloquinoxalinamines.

ChemInform Abstract: A Four‐Component Synthesis of Novel Spiro[pyrazoloquinoline‐oxindoles] under Solvent‐Free Conditions.

AbstractThe four‐component reaction is limited to naphthylamines.

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 nm that 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.

A four-component synthesis of novel spiro[pyrazoloquinoline-oxindoles] under solvent-free conditions

A domino reaction for the rapid and diverse synthesis of spiro[1H-pyrazolo[3,4-b]benzo[h]dihydroquinolin-4,3-indolin-2-ones] is reported. The synthesis represents a thermodynamically-favored four-component reaction between phenylhydrazine, isatins, naphthylamines, and 3-ketoesters giving the novel products in excellent yields under solvent-free conditions. Similar applications of anilines in place of naphthylamines have not led to formation of the expected 4-substituted pyrazolo[3,4-b]quinoline derivatives. The difference was ascribed to lower aromatic character of naphthylamines, with respect to anilines, which enables them to act easier as enamines in reaction with the postulated intermediates formed from condensation of isatins and the in situ generated pyrazolones. Surprisingly, 6-aminouracils in despite of their known enamine properties did not participate in reaction with isatins and pyrazolones, the merit of naphthylamines for this synthesis seems to be met by the favorable balance of their N- and C-nucleophilicity.

Synthesis of functionalized dispiro-oxindoles through azomethine ylide dimerization and mechanistic studies to explain the diastereoselectivity

Synthesis of functionalized dispiro-oxindoles via [3 + 3]-cycloaddition of azomethine ylide generated from condensation of isatin and proline is reported. A transition state model for the origin of diastereoselectivity and mechanism of formation of these types of adducts is proposed.

ChemInform Abstract: Synthesis of Spiro[pyrazolo[3,4‐b]pyridine‐4,3′‐indoline] and Spiro[benzo[h]pyrazolo[3,4‐b]quinoline‐4,3′‐indoline] Derivatives Using Wet Cyanuric Chloride under Solvent‐Free Conditions.

AbstractThe title compounds (IV), (VI) are efficiently obtained by one‐pot condensation of isatins, pyrazolamine and Meldrum′s acid or hydroxynaphthoquinone within relatively short reaction times.

Synthesis, spectroscopic characterisation, DNA cleavage, superoxidase dismutase activity and antibacterial properties of some transition metal complexes of a novel bidentate Schiff base derived from isatin and 2-aminopyrimidine

Complexes of manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II) with a Schiff base, formed by the condensation of isatin with 2-aminopyrimidine have been synthesised and characterised through elemental analysis, molar conductance measurements, magnetic susceptibility, IR, UV–Vis, 1HNMR, FAB mass and EPR spectral studies. The spectral data revealed that the ligand acts as neutral bidentate, coordinating to the metal ion through the carbonyl oxygen and azomethine nitrogen. Molar conductance values adequately support the electrolytic nature of the complexes. On the basis of the above observations the complexes have been formulated as [M(ISAP)2]X2, where M=Mn(II), Co(II), Ni(II), Cu(II) and Zn(II); X=Cl, OAc; ISAP=2-[N-indole-2-one]aminopyrimidine. The ligand and copper(II) complex were subjected to X-ray diffraction studies. The DNA cleavage study was monitored by gel electrophoresis method. The superoxide dismutase (SOD) mimetic activities of the ligand and the metal complexes were checked using NBT assay. The in vitro antibacterial activity of the synthesized compounds has been tested against gram negative and gram positive bacteria.

ChemInform Abstract: Carbon—SO3H: A Novel and Recyclable Solid Acid Catalyst for the Synthesis of Spiro[4H‐pyran‐3,3′‐oxindoles

AbstractThe title catalyst, derived from bioglycerol, is successfully used for the one‐pot three‐component condensation of isatins or acenaphthenequinone with 1,3‐dicarbonyl compounds and malononitrile or ethyl cinnnamate.

ChemInform Abstract: Utility of Cyano‐N‐(2‐oxo‐1,2‐dihydroindol‐3‐ylidene)acetohydrazide in the Synthesis of Novel Heterocycles.

Cyano-N-(2-oxo-1,2-dihydroindol-3-ylidene)acetohydrazide was prepared by condensation of isatin with cyanoaceto-hydrazide in refluxing 1,4-dioxane. Subsequent reaction with a variety of electrophil...