A general and inexpensive protocol for the nanomagnetic 5-sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo
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ORIGINAL PAPER
A general and inexpensive protocol for the nanomagnetic 5‑sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo[b] pyrans and quinoxaline derivatives Farzaneh Saboury1 · Najmedin Azizi2 · Zohreh Mirjafari1 · Mohammad Mahmoudi Hashemi1 Received: 17 January 2020 / Accepted: 27 April 2020 © Iranian Chemical Society 2020
Abstract In this study, a novel acid-functionalized magnetic nanoparticles with high loaded multifunctional acidic groups was fabricated by anchoring water-soluble 5-sulfosalicylic acid onto the surface silica-modified F e3O4. The magnetically recyclable Fe3O4@SiO2@5-SA (20 mg) showed excellent reactivity for greener synthesis of tetrahydrobenzo[b]pyrans via a threecomponent reaction of different aromatic aldehydes, malononitrile and dimedone in good to excellent yields (70–95%) in pure water at short reaction times (40–150 min). The method shows eco-friendly synthesis of quinoxaline derivatives from direct condensation of substituted 1,2-diamine with various 1,2-dicarbonyl in ethanol at room temperature to afford the desired quinoxalines with good to excellent yields (60–97%) at shorter reaction times (120–240 min). The morphology and magnetic properties of MNPs were studied with scanning electron microscopy, X-ray powder diffraction, Fourier translation infrared spectroscopy, vibrating sample magnetometer and thermogravimetric. The results showed that the F e3O4@SiO2@5SA catalyst is completely recoverable by an external magnet and retained catalytic activity after five recycles. Keywords 5-Sulfosalicylic acid · Green chemistry · Magnetic nanoparticle · Multicomponent reaction · Tetrahydrobenzo[b] pyrans · Quinoxaline derivatives
Introduction The heterocyclic pyran and quinoxaline scaffold is a widely distributed structural framework with an extensive array of biotic and pharmacological properties such as antiphlogistic, antidepressant, anticonvulsant and antibacterial activity [1]. Quinoxaline ring constitutes as a part of various inhibitors of numerous targets such as HCV protease and activity as kinase inhibitors [2]. Pyran and some of its derivatives are useful to meet the higher sensitivity and selectivity between organic chemistry and materials science [3]. Thus, the synthesis of pyran and quinoxaline derivatives is attracting interest for the past several decades and significant
* Najmedin Azizi [email protected] 1
Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335‑186, Tehran, Iran
2
approaches have been developed through traditional methods or multicomponent reactions [4–12]. Magnetic nanocomposites are key focus and challenge for academic and industrial researchers as magnetic supports in diverse fields due to the abundant, inexpensive, environmentally benign properties [13, 14]. In particular, F e 3O 4 nanoparticles (MNPs) have unique advantages such as nontoxic, high surface area, readily accessible, abundant and retrievable wh
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