Butane‐1‐sulfonic acid immobilized on magnetic Fe₃O₄@SiO₂ nanoparticles: A novel and heterogeneous catalyst for the one‐pot synthesis of barbituric acid and pyrano[2,3‐d] pyrimidine derivatives in aqueous media

Abstract

Butane‐1‐sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2‐Sultone) was easily prepared via direct ring opening of 1,4‐butanesultone with nanomagnetic Fe3O4@SiO2. The prepared reagent was characterized and used for the efficient promotion of the synthesis of barbituric acid and pyrano[2,3‐d] pyrimidine derivatives. All reactions were performed under mild and completely heterogeneous reaction conditions affording products in good to high yields. The catalyst is easily isolated from the reaction mixture by magnetic decantation and can be reused at least eight times without significant loss in activity.

Synthesis of Silica-Based Solid-Acid Catalyst Material as a Potential Osteochondral Repair Model In Vitro

“…The broad peak near 3,490 cm −1 was assigned to N-H stretching vibrations, while the peaks at 2,936 and 2,873 cm −1 were attributed to C-H stretching vibrations. The peak at 1,084 cm −1 arises from the stretching vibration of Si-O-Si, but due to the overlap of S O and Si-O-Si characteristic peaks around 1,100 cm −1 , the half-peak at 1,118 cm −1 was considered to be the stretching vibration peak of S O (Pourghasemi-Lati et al, 2018). In the low wavenumber region, some characteristic sulfonic acid peaks also overlapped with SiO 2 , and the peaks at 617 and 616 cm −1 could be stretching vibrations of S-O.…”

“…Silica is preferred as a carrier for its stability in most solvents, and Niknam and coworkers (Niknam et al, 2010) successfully prepared silica-bonded S-sulfonic acid (SBSSA) and employed it as a recyclable catalyst for the condensation reaction of aromatic aldehydes with 3-methyl-l-phenyl-5-pyrazolone. With continued catalyst development, Pourghasemi-Lati and colleagues (Pourghasemi-Lati et al, 2018) immobilized butane-1-sulfonic acid on magnetic Fe 3 O 4 @SiO 2 nanoparticles for the synthesis of 5-arylidine barbituric acids and pyrano [2,3-d] pyrimidine derivatives. In addition, silica-based biomaterials have been widely studied in bone and cartilage tissue engineering due to high mechanical stiffness, high biocompatibility, and special bioactivities including stimulating osteogenesis and angiogenesis by enhancing corresponding gene expressions (Li et al, 2000;Du et al, 2015;Ishikawa et al, 2018).…”

WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3‐d]pyrimidinones as inhibitors of SARS‐CoV‐2

“…Given this, a large number of catalysts were introduced for the three‐component synthesis of tetrahydrobenzo[ b ]pyran and pyrano[2,3‐ d ]‐pyrimidinone/thiones under multifarious catalytic circumstances. [ 9 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ] There are numerous catalysts derived from fruit extracts, and agro‐wastes have been utilized to synthesize various heterocycles. [ 35 , 36 , 37 , 38 , 39 ]…”

Microwave‐associate synthesis of Co3O4 nanoparticles as an effcient nanocatalyst for the synthesis of arylidene barbituric and Meldrum's acid derivatives in green media

“…This condensation is a significant and practical reaction for the carbon–carbon bond formation in organic synthesis. Substituted barbituric and thiobarbituric acid derivatives have diverse biological activities such as antispasmodic, anticancer, anticonvulsant, sedative, complex and salt forming reagents . Arylidene analogues of Meldrum's acid are vital mediators in cycloaddition responses, synthesizing heterocyclic composites that are biologically profound (e.g., cardiotonic28a and HIV integrase hindrance behavior28b).…”