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An efficient synthesis of 3-indolyl-3-hydroxy oxindoles and 3,3-di(indolyl)indolin-2-ones catalyzed by sulfonated β-CD as a supramolecular catalyst in water.

ABSTRACT: Sulfonated-β-cyclodextrin (β-CD-SO₃H) promoted efficient and fast electrophilic substitution reaction of indoles with various isatins reflux in water is reported affording various 3-indolyl-3-hydroxy oxindoles and 3,3-di(indolyl)indolin-2-ones in good to excellent yields in short reaction time.

SUBMITTER: Tayade YA

PROVIDER: S-EPMC7111843 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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An efficient synthesis of 3-indolyl-3-hydroxy oxindoles and 3,3-di(indolyl)indolin-2-ones catalyzed by sulfonated β-CD as a supramolecular catalyst in water.

Tayade Yogesh A YA Patil Dipak R DR Wagh Yogesh B YB Jangle Asha D AD Dalal Dipak S DS

Tetrahedron letters 20141212 5

Sulfonated-β-cyclodextrin (β-CD-SO<sub>3</sub>H) promoted efficient and fast electrophilic substitution reaction of indoles with various isatins reflux in water is reported affording various 3-indolyl-3-hydroxy oxindoles and 3,3-di(indolyl)indolin-2-ones in good to excellent yields in short reaction time. ...[more]

PMID: 32287446

Similar Datasets

Synthesis, α-glucosidase inhibition, α-amylase inhibition, and molecular docking studies of 3,3-di(indolyl)indolin-2-ones.

Project description:The synthesized 3,3-di(indolyl)indolin-2-ones 1a-p showed desired higher α-glucosidase inhibitory activities and lower α-amylase inhibitory activities than standard drug acarbose. Particularly, compound 1i showed favorable higher α-glucosidase % inhibition of 67 ± 13 and lower α-amylase % inhibition of 51 ± 4 in comparison to acarbose with % inhibition activities of 19 ± 5 and 90 ± 2, respectively. Docking studies of selected 3,3-di(indolyl)indolin-2-ones revealed key interactions with the active sites of both α-glucosidase and α-amylase, further supporting the observed % inhibitory activities. Furthermore, the binding energies are consistent with the % inhibition values. The results suggest that 3,3-di(indolyl)indolin-2-ones may be developed as suitable Alpha Glucosidase Inhibitors (AGIs) and the lower α-amylase activities should be advantageous to reduce the side effects exhibited by commercial AGIs.

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Silica-Coated Magnetic-Nanoparticle-Supported DABCO-Derived Acidic Ionic Liquid for the Efficient Synthesis of Bioactive 3,3-Di(indolyl)indolin-2-ones.

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1-Allyl-3,3-diphenyl-indolin-2-one.

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Site-specific role of bifunctional graphitic carbon nitride catalyst for the sustainable synthesis of 3,3-spirocyclic oxindoles in aqueous media.

Project description:Functionalized graphitic carbon nitride (Sg-C3N4) has been manufactured and used as a reusable catalyst for the one-pot production of various spiro-pyrano chromenes and spiro indole-3,1'-naphthalene tetracyclic systems in aqueous media. An ultrasound-assisted method has been used for the functionalization of g-C3N4. The catalytic functionalities and the structural integrity of the catalyst were characterized via different analytical tools. The catalytic site-specific role of Sg-C3N4 was confirmed via various control experiments in one-pot reaction sequences. We recognized that Sg-C3N4 acts as a bifunctional acid-base catalyst for the first reaction sequence whereas it is an acidic catalyst for the second reaction sequence during the one-pot production of various spiro-pyrano chromenes. In addition, the bifunctional acid-base catalytic role of Sg-C3N4 has been confirmed for the first reaction sequence whereas it has a basic catalytic role for the second reaction sequence during the one-pot production of spiro indole-3,1'-naphthalene tetracyclic systems. Diverse C-C, C-O, and C-N bonds, six-membered cycles, stereogenic centers, and spiro frameworks were formed in a single reaction, enhancing the biocidal profile and possibly resulting in the discovery of new medicinal properties. The mild reaction environment, simple workup, easy separation, low cost, heterogeneity, and recyclability of Sg-C3N4 are some rewards of this approach.

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3,3-Dichloro-1-(chloro-meth-yl)indolin-2-one.

Project description:In the title compound, C(9)H(6)Cl(3)NO, the pyrrole ring is almost coplanar with the benzene ring [dihedral angle = 1.90 (9)°], while the Cl-C-N-C torsion angle is 98.78 (17)°. In the crystal, pairs of mol-ecules are inter-connected by pairs of Cl⋯Cl inter-actions [3.564 (5) Å], forming dimers, which are further peripherally connected through inter-molecular C-H⋯O=C and π-π inter-actions [centroid-centroid distances = 4.134 (7), 4.134 (6) and 4.238 (7) Å], forming a two-dimensional network.

| S-EPMC3009249 | biostudies-literature

1-Allyl-3,3-di-p-tolyl-indolin-2-one.

Project description:In the title compound, C(25)H(23)NO, the indoline system is essentially planar. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯N inter-actions and the crystal packing is determined by inter-molecular C-H⋯π inter-actions.

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3-(4-Hydroxy-phenyl-imino)indolin-2-one.

Project description:In the title compound, C(14)H(10)N(2)O(2), the dihedral angle between the indole and benzene rings is 61.63 (4)°. In the crystal structure, centrosymmetrically related mol-ecules are linked into dimers by N-H⋯O hydrogen bonds, generating rings of graph-set motif R(2) (2)(8). The dimers are further connected into a three-dimensional network by O-H⋯O and C-H⋯O hydrogen bonds.

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Sulfonated magnetic spirulina nanobiomaterial as a novel and environmentally friendly catalyst for the synthesis of dihydroquinazolin-4(1H)-ones in aqueous medium.

Project description:Spirulina algae is an excellent candidate for catalyst preparation due to its reactive functional groups, cost-effectiveness, widespread commercial accessibility, and biodegradability. In this study, magnetized Spirulina was used for the synthesis of dihydroquinazolin-4(1H)-ones (DHQZs) as catalyst. Magnetized Spirulina was produced by CoFe2O4 and sulfonation method using chlorosulfonic acid to create the catalyst [CoFe2O4-Sp-SO3H]. It was affirmed by various techniques, including Fourier transform infrared (FT-IR), Vibrating sample magnetometry (VSM), Powder X-ray diffraction (XRD), Energy-dispersive X-ray spectroscopy (EDS), Thermogravimetric analysis (TGA), Transmission electron microscopy (TEM), Field emission scanning electron microscopy (FE-SEM), and elemental mapping techniques. DHQZs synthesis was accomplished through a concise one-pot, three-component reaction involving a range of diverse aldehydes, isatoic anhydride, and primary aromatic amine, within an aqueous medium. The method offers several advantages, including using green conditions, the generation of several new 2-furan-quinazolinone derivatives, chromatography-free purification, short reaction times, appropriate yield of product (75-96%), and catalyst recyclability. The proposed catalyst and water as solvent demonstrated a strong synergistic effect, leading to the prosperous synthesis of various novel dihydroquinazolinones at 60 °C. These numerous benefits make our approach highly attractive for academic research and industrial applications.

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Crystal structures of 5,5'-bis(-hydroxy-methyl)-3,3'-biisoxazole and 4,4',5,5'-tetrakis-(hydroxy-methyl)-3,3'-biisoxazole.

Project description:The mol-ecular structure of 5,5'-bis(-hydroxy-methyl)-3,3'-biisoxazole, C8H8N2O4 (1), is composed of two trans planar isoxazole rings [r.m.s deviation = 0.006 (1) Å], each connected with a methyl hydroxyl group. Similarly, the structure of 4,4',5,5'-tetrakis-(hydroxy-methyl)-3,3'-biisoxazole, C10H12N2O6 (2), is composed of two planar isoxazole rings [r.m.s. deviation = 0.002 (1) Å], but with four hydroxymethyl groups as substituents. Both mol-ecules sit on a center of inversion, thus Z' = 0.5. The crystal structures are stabilized by networks of O-H⋯N [for (1)] and O-H⋯O hydrogen-bonding inter-actions [for (2)], giving rise to corrugated supra-molecular planes. The isoxazole rings are packed in a slip-stacked fashion, with centroid-to-centroid distances of 4.0652 (1) Å for (1) (along the b-axis direction) and of 4.5379 (Å) for (2) (along the a-axis direction).

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