352329-70-5Relevant articles and documents
Highly efficient and green synthesis of spiro[indoline-3,9′-xanthene]trione and spiro[chromene-4,3′-indoline]-3-carbonitrile derivatives in water catalyzed by graphene oxide-supported dicationic ionic liquid
Patel, Nipun,Patel, Unnati,Dadhania, Abhishek
, p. 2189 - 2206 (2021/02/21)
In this article, a mild and highly efficacious synthetic route has been developed for the synthesis of spiro[indoline-3,9′-xanthene]trione and spiro[chromene-4,3′-indoline]-3-carbonitrile derivatives using graphene oxide-supported dicationic ionic liquid (DIL@GO) as a heterogeneous catalyst in aqueous media. Targeted spiro[indoline-3,9′-xanthene]trione derivatives were synthesized via one-pot condensation of substituted isatins and 1,3-diketone compounds (1,3-cyclohexanedione/dimedone), and spiro[chromene-4,3′-indoline]-3-carbonitrile derivatives were synthesized via one-pot reaction of substituted isatins, malononitrile, and enolizable C-H-activated compounds (2-hydroxynaphthalene-1,4-dione/dimedone). The DIL@GO catalyst demonstrated outstanding catalytic capabilities in all the tested reactions and yielded excellent isolated yields of the final products within a short reaction time. Additionally, the heterogeneous nature of the catalyst facilitates catalyst separation through centrifugation, and its reusability up to five successive reaction cycles with retention in activity makes this methodology more advantageous and environmentally benign. Graphic abstract: [Figure not available: see fulltext.]
Guanine base stabilized on the magnetic nanoparticles as recyclable catalyst “on water” for the synthesis of spirooxindole derivatives
Azizi, Zohre,Bashkar, Mohammad,Niknam, Khodabakhsh,Rezaei, Arash,Saberi, Dariush
, (2021/06/15)
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.
Synthesis of functionalized chromene and spirochromenes using L-proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
Nagaraju, Sakkani,Paplal, Banoth,Sathish, Kota,Giri, Santanab,Kashinath, Dhurke
supporting information, p. 4200 - 4204 (2017/10/06)
An efficient and recyclable homogeneous catalyst is developed using commercially cheap L-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, L-proline and melamine (3:1 ratio; 3 mol% on total weight) was found to be best catalyst to give the desired products with excellent yields (up to 99%) in very short times (1–15 min) at room temperature in DMSO as solvent. The catalyst was recovered by adding EtOAc and reused up to 5 cycles without losing the catalytic activity.
