Synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by poly(ferric 2-acrylamido-2-methylpropanesulfonate)
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ORIGINAL PAPER
Synthesis of 3,4‑dihydropyrimidin‑2(1H)‑ones catalyzed by poly(ferric 2‑acrylamido‑2‑methylpropanesulfonate) Zhihao Zhao1 · Hongguang Dai1 · Lan Shi1 Received: 28 May 2020 / Accepted: 17 August 2020 © Institute of Chemistry, Slovak Academy of Sciences 2020
Abstract Poly(ferric 2-acrylamido-2-methylpropanesulfonate) (PFAMPS) was prepared via the reaction of poly(2-acrylamido-2-methylpropanesulfonic acid) and Fe(OH)3. PFAMPS was used as a heterogeneous catalyst for the Biginelli reaction of aldehyde, ethyl acetoacetate, and urea to synthesize 3,4-dihydropyrimidin-2(1H)-ones with yields of 70–87%. PFAMPS can be recycled six times without significant loss in catalytic activity. For comparison, ferric lignosulfonate (FLSA), ferric cellulose sulfonate (FCSA), ferric starch sulfonate (FSSA), and ferric 732 cation exchange resin (FACER) were used as catalysts of the Biginelli reaction. It was shown that the catalytic activities of recycled FLSA, FCSA, FSSA, and FACER significantly decreased after two reactions. Fe3+ in the polymer sulfonates acted as the catalyst for the Biginelli reaction. PFAMPS was the chelate, where the action between F e3+ and the poly(2-acrylamido-2-methylpropanesulfonate) matrix was strong, and 3+ Fe lost little from the PFAMPS. However, significant Fe3+ loss was observed in the FLSA, FCSA, FSSA and FACER polymer matrices after reuse. Keywords Biginelli reaction · Catalyst · Poly(ferric 2-acrylamido-2-methylpropanesulfonate) · Synthesis
Introduction 3,4-Dihydropyrimidin-2(1H)-ones exhibit biological and pharmacological activities, and are widely used as calcium channel antagonists, anti-bacterial, anti-hypertensive, and anti-inflammatory agents (Tayebee and Ghadamgahi 2017). In 1893, Pietro Biginelli (1893) first reported the synthesis of 3,4-dihydropyrimidin-2(1H)-one (DHPM) by a simple one-pot condensation reaction of aromatic aldehydes, β-ketoesters and urea under strongly acidic conditions (Tayebee and Ghadamgahi 2017). In recent decades, a number of catalysts for the Biginelli reaction were studied by researchers, such as calix[8]arene sulfonic acid (An et al. 2016), phthalic acid (Mohamadpour et al. 2018), zirconium(IV) 4-sulphophenylethyliminobismethylphosphonate (Yang et al. 2011), gallium(III) triflate (Li et al. 2010), Co(NO3)2 (NasrEsfahani et al. 2014), iron(III) tosylate (Starcevich et al. 2013), 3-[(3-(trimethoxysilyl)propyl)thio]propane-1-oxysulfonic acid (Jetti et al. 2017), mesoporous NH4H2PO4/ * Hongguang Dai [email protected] 1
College of Science, Inner Mongolia Agricultural University, Hohhot 010018, People’s Republic of China
MCM-41 (Tayebee and Ghadamgahi 2017), phosphotungstic acid grafted zeolite imidazolate (Tayebee et al. 2019), Fe3O4@meglumine sulfonic acid (Moradi and Tadayon 2018), sulfated graphene and graphene oxide (Vessally et al. 2017), ionic liquid 1,3-disulfonic acid benzimidazolium chloride (Abbasi 2016), Pb/Cu (Mathur et al. 2018), Fe+3-montmorillonite K10 (Fekri et al. 2017), Co@imineNa+-MMT (Khorshidi et al. 2017), metal-suppo
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