5,5’-Indigodisulfonic acid as an efficient catalyst for the synthesis of 2,3-dihydroquinazolinone derivatives

Liu, Cheng‐Hang; Wang, Qiong; Xu, Zhi‐Kang; Li, Dongling; Zheng, Yun‐Wen

doi:10.1080/00397911.2022.2098045

Cited by 8 publications

(2 citation statements)

References 36 publications

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“…2‐(2‐Bromophenyl)‐2,3‐dihydroquinazolin‐4(1 H )‐one (Table 2, product entry 3h) Pale yellow solid, M.P‐172–174°C 45 ; IR (KBr) cm −1 : 3302, 3184, 3052, 1661, 1602, 1500, 1480; 1 H‐NMR (400 MHz, DMSO‐ d 6 ): δ (ppm): δ 8.25 (s, 1H), 7.78–7.68 (m, 3H), 7.50 (t, J = 7.2 Hz, 1H), 7.42–7.28 (m, 2H), 7.04 (s, 1H), 6.86–6.73 (m, 2H), 6.16 (s, 1H); 13 C NMR (100 MHz, DMSO‐ d 6 ):δ (ppm): 164.21, 148.29, 139.73, 134.02, 133.38, 131.29, 129.71, 128.66, 127.97, 122.80, 118.10, 115.30, 115.19, 66.97.…”

Section: Methodsmentioning

confidence: 99%

Design and synthesis of γ‐Fe₂O₃@Ag‐S‐CH₂‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and their anti‐skin cancer activity

Gurav

Gurav²,

Zond

et al. 2023

Applied Organom Chemis

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The ongoing work describes the catalytic evaluation of γ‐Fe2O3@Ag‐S‐CH2‐COOH magnetic nanoparticles utilizing γ‐Fe2O3 obtained from waste iron rust for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones. As‐prepared γ‐Fe2O3@Ag‐S‐CH2‐COOH nanoparticles were characterized by Fourier transform infrared spectroscopy (FT‐IR), X‐ray diffraction (XRD), scanning electron microscopy (SEM), energy‐dispersive X‐ray spectroscopy (EDX), dynamic light scattering (DLS), transmission electron microscopy (TEM), X‐ray photoelectron spectroscopy (XPS), and Brunauer–Emmett–Teller (BET) technique. The catalytic performance of greener γ‐Fe2O3@Ag‐S‐CH2‐COOH nanoparticles was utilized in the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones. The excellent catalytic performance was shown by magnetic nanoparticles in addition to its ease of separation by an external magnet and can be recycled for five consecutive turns without significant loss of catalytic activity. Furthermore, the synthesized 2,3‐dihydroquinazolin‐4(1H)‐ones were confirmed by FT‐IR, 1H, 13C nuclear magnetic resonance (NMR), and mass spectrometry. Moreover, the synthesized 2,3‐dihydroquinazolin‐4(1H)‐ones were evaluated for their anticancer efficiency against the human skin cancer cell line B16F10 along with molecular docking investigation.

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Section: Methodsmentioning

confidence: 99%

Design and synthesis of γ‐Fe₂O₃@Ag‐S‐CH₂‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and their anti‐skin cancer activity

Gurav

Gurav²,

Zond

et al. 2023

Applied Organom Chemis

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“…In recent years, there have been numerous reports on the synthesis of 2,3-dihydroquinazolin-4(1H)-ones using diverse catalysts, such as Fe 3 O 4 @SiO 2 @TiO 2 -OSO 3 H 22 , 5,5'-Indigodisulfonic acid 23 , MCM-41-SO 3 H 24 , SCMNPs-Pr-HMTA-SO 3 H 25 , Al(H 2 PO 4 ) 3 26 , CoAl 2 O 4 Nanoparticles 27 , SnCl 2 .2H 2 O 28 , Fe 3 O 4 @EDTA/CuI 29 , SiO 2 –H 3 PW 12 O 40 30 , Co aminobenzamid@Al SBA 15 31 , Boric Acid Supported on Montmorillonites 32 . However, most of these procedures have certain limitations, such as lengthy procedures, harsh reaction conditions, hazardous and volatile organic solvents, application of expensive and unavailable reagents, and non-reusability of the catalyst.…”

Section: Introductionmentioning

confidence: 99%

Sulfonated magnetic spirulina nanobiomaterial as a novel and environmentally friendly catalyst for the synthesis of dihydroquinazolin-4(1H)-ones in aqueous medium

Mashhadi,

Safaei-Ghomi

2024

Sci Rep

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Spirulina algae is an excellent candidate for catalyst preparation due to its reactive functional groups, cost-effectiveness, widespread commercial accessibility, and biodegradability. In this study, magnetized Spirulina was used for the synthesis of dihydroquinazolin-4(1H)-ones (DHQZs) as catalyst. Magnetized Spirulina was produced by CoFe2O4 and sulfonation method using chlorosulfonic acid to create the catalyst [CoFe2O4-Sp-SO3H]. It was affirmed by various techniques, including Fourier transform infrared (FT-IR), Vibrating sample magnetometry (VSM), Powder X-ray diffraction (XRD), Energy-dispersive X-ray spectroscopy (EDS), Thermogravimetric analysis (TGA), Transmission electron microscopy (TEM), Field emission scanning electron microscopy (FE-SEM), and elemental mapping techniques. DHQZs synthesis was accomplished through a concise one-pot, three-component reaction involving a range of diverse aldehydes, isatoic anhydride, and primary aromatic amine, within an aqueous medium. The method offers several advantages, including using green conditions, the generation of several new 2-furan-quinazolinone derivatives, chromatography-free purification, short reaction times, appropriate yield of product (75–96%), and catalyst recyclability. The proposed catalyst and water as solvent demonstrated a strong synergistic effect, leading to the prosperous synthesis of various novel dihydroquinazolinones at 60 °C. These numerous benefits make our approach highly attractive for academic research and industrial applications.

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Synthesis of biologically active dihydroquinazolinone catalyzed by the micro–meso-composite of zeolite H-BEA

2023

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5,5’-Indigodisulfonic acid as an efficient catalyst for the synthesis of 2,3-dihydroquinazolinone derivatives

Cited by 8 publications

References 36 publications

Design and synthesis of γ‐Fe₂O₃@Ag‐S‐CH₂‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and their anti‐skin cancer activity

Design and synthesis of γ‐Fe₂O₃@Ag‐S‐CH₂‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and their anti‐skin cancer activity

Sulfonated magnetic spirulina nanobiomaterial as a novel and environmentally friendly catalyst for the synthesis of dihydroquinazolin-4(1H)-ones in aqueous medium

Synthesis of biologically active dihydroquinazolinone catalyzed by the micro–meso-composite of zeolite H-BEA

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5,5’-Indigodisulfonic acid as an efficient catalyst for the synthesis of 2,3-dihydroquinazolinone derivatives

Cited by 8 publications

References 36 publications

Design and synthesis of γ‐Fe2O3@Ag‐S‐CH2‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and their anti‐skin cancer activity

Design and synthesis of γ‐Fe2O3@Ag‐S‐CH2‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and their anti‐skin cancer activity

Sulfonated magnetic spirulina nanobiomaterial as a novel and environmentally friendly catalyst for the synthesis of dihydroquinazolin-4(1H)-ones in aqueous medium

Synthesis of biologically active dihydroquinazolinone catalyzed by the micro–meso-composite of zeolite H-BEA

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Design and synthesis of γ‐Fe₂O₃@Ag‐S‐CH₂‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and their anti‐skin cancer activity

Design and synthesis of γ‐Fe₂O₃@Ag‐S‐CH₂‐COOH nanocatalyst for one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and their anti‐skin cancer activity