High-efficient synthesis of 2-imino-2 H -chromenes and dihydropyrano[ c ]chromenes using novel and green catalyst (CaO@S
- PDF / 1,834,908 Bytes
- 19 Pages / 439.37 x 666.142 pts Page_size
- 60 Downloads / 187 Views
High‑efficient synthesis of 2‑imino‑2H‑chromenes and dihydropyrano[c]chromenes using novel and green catalyst (CaO@SiO2@AIL) Fatemeh Sameri1,2 · Akbar Mobinikhaledi1,2 · Mohammad Ali Bodaghifard1,2 Received: 12 August 2020 / Accepted: 3 October 2020 © Springer Nature B.V. 2020
Abstract In this work, 1,3,5,7-tetraazaadamantan-1-ium chloride (AIL) functionalized silicacoated calcium oxide hybrid nanocatalyst (CaO@SiO2@AIL) as a novel, efficient, green and recyclable heterogeneous ionic liquid catalyst was synthesized. Catalytic activity of the CaO@SiO2@AIL hybrid nanoparticles was investigated for synthesis of the pharmaceutically valuable 2-imino-2H-chromene and dihydropyrano[c] chromene derivatives. A wide range of amines and aromatic aldehydes containing either electron-withdrawing or electron-donating substituent were examined using optimized conditions to produce the desired products. 2-Imino-2H-chromenes were synthesized under solvent-free condition, and dihydropyrano[c]chromenes were prepared in aqueous medium as green conditions within short reaction times, high yields and using easy workup procedures. Structure confirmation and surface properties of the core/shell hybrid nanoparticles were considered via Fourier transform infrared spectroscopy, X-ray powder diffraction, scanning electron microscope, energy-dispersive X-ray spectroscopy, WDS map scan, thermogravimetric and elemental analyses. This IL-supported heterogeneous nanocatalyst can be reused at least six times without considerable loss of its performance. Keywords Ionic liquid · Eggshells waste · Biocatalyst · 2-Imino-2H-chromenes · Dihydropyrano[c]chromenes
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04295-5) contains supplementary material, which is available to authorized users. * Akbar Mobinikhaledi [email protected] 1
Department of Chemistry, Faculty of Science, Arak University, Arāk 38156‑88138, Iran
2
Institute of Nanosciences and Nanotechnology, Arak University, Arāk 38156‑88138, Iran
13
Vol.:(0123456789)
F. Sameri et al.
Introduction Heterocyclic motifs with anticancer and anti-HIV properties play a notable role in design and synthesis of bioactive molecules [1, 2]. The chromene derivatives are an important type of heterocyclic compounds, which have received considerable attention due to their biological and pharmacological properties and critical intermediates in the synthesis of many natural products and medicinal agents [3], such as anticancer, antibacterial [4], antiviral [5], antimicrobial [6] and anti-HIV [7] activities. They have also been widely employed as cosmetics, pigments, potent biodegradable agrochemicals [8] and are found in several natural tocopherols, alkaloids, anthocyanins and flavonoids [9]. In this sense, chromene’s structural matter exists in several significant biologically active compounds like 2-imino-2H-chromenes. Functionalized 2-imino-2Hchromenes have attracted widespread attention due to their different applications, includi
Data Loading...
