Chitosan magnetic nanocomposite: a magnetically reusable nanocatalyst for green synthesis of Hantzsch 1,4-dihydropyridin
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ORIGINAL RESEARCH
Chitosan magnetic nanocomposite: a magnetically reusable nanocatalyst for green synthesis of Hantzsch 1,4‑dihydropyridines under solvent‑free conditions Parichehr Kamalzare1 · Behrooz Mirza1 · Somayeh Soleimani‑Amiri1 Received: 12 July 2020 / Accepted: 9 October 2020 © Islamic Azad University 2020
Abstract An environmentally friendly method for the efficient synthesis of biologically active 1,4-dihydropyridine derivatives has been performed. The reaction was carried out under solvent-free conditions using chitosan magnetic nanocomposite of Ch-Rhomboclase as an efficient heterogeneous recyclable catalyst. The chitosan magnetic nanocomposite was synthesized through a comfortable and reasonably priced method. It was specified by FT-IR, XRD, EDS, SEM, TEM, VSM, and TGA analyses. Mild reaction conditions, absence of toxic solvent, low catalyst loading, high speed and efficiency, magnetically removable catalyst, and reusability of catalyst are the most important advantages of this method for the synthesis of Hantzsch 1,4-dihydropyridines.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s40097-020-00361-x) contains supplementary material, which is available to authorized users. * Behrooz Mirza [email protected]; [email protected] * Somayeh Soleimani‑Amiri [email protected]; [email protected] 1
Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran
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Vol.:(0123456789)
Journal of Nanostructure in Chemistry
Graphic abstract
OH
O
O
H2N
HO O NH2 OH rh o OH OH O
rh o
NH2 O
O
OH HO rh o H2N NH2
OH rho
O
HO O
HO rh o
OH
OH
O HO H2N rh o
O
NH2 O
Ch-Rhomboclase NCs
Ar R2
R2
CHO O
O
Ar
O
O R2
O R3
O NH4OAC
R3
Solvent-Free 80 °C
R2 R3
N H
R3
(4a-q, 5a-f)
Keyword Chitosan magnetic nanocomposite · Heterogeneous catalyst · Hantzsch condensation · 1,4-Dihydropyridines · Solvent-free
Introduction The 1,4-dihydropyridine derivatives (DHP) are found in many pharmaceutical compounds. These compounds have attracted a lot of attention due to their numerous therapeutic and medicinal activities [1]. These can be used as drugs to the blood vessels dilation and liver protection. The DHPs are also anti-wrinkle, anti-asthma, anti-tumor, anti-aging, and anti-diabetic drugs [2]. Moreover, 4-substituted 1,4-dihydropyridines have been identified as calcium channel blockers and also have been known as one of the most valuable types of drugs for cardiovascular disease treatment. Accordingly, numerous methods have been reported for the synthesis of 1,4-dihydropyridine derivatives so far. The organic chemistry has found new approaches to designing and synthesizing novel heterocyclic compounds through a multicomponent reaction (MCR) with an
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ecologically acceptable perspective. The MCR has emerged as an effectual and powerful device in modern synthetic organic chemistry. MCRs, through a simple one-step reaction with high atom-economy and high selectivity, replaced the classical method with sequential syn
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