Sulfated tin oxide (SO4−2/SnO2): an efficient heterogeneous solid superacid catalyst for the facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones

Gajare, Shivanand; Kagne, Raju; Kukade, Mahesh G.; Pawar, Arvind; Rashinkar, Gajanan; Tamhankar, Bhaskar

doi:10.1007/s11164-022-04670-4

Cited by 9 publications

(10 citation statements)

References 59 publications

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“…2‐(4‐Nitrophenyl)‐2,3‐dihydroquinazolin‐4(1 H )‐one (Table 2, product entry 3a, Figures S1–S4) Yellow solid, M.P‐200–202°C 41–43 ; IR (KBr) cm −1 : 3362, 3390, 2923, 2373, 1660, 1612, 1513; 1 H NMR (400 MHz, DMSO‐ d 6 ): δ (ppm): δ 8.07–8.11 (m, J = 8 Hz, 2H), 7.93 (s, 1H), 7.63–7.67 (d, J = 8 Hz, 3H), 7.13–7.17 (m, 1H), 6.61–6.69 (m, J = 8 Hz, 3H), 5.83 (s, 1H); 13 C NMR (100 MHz, DMSO‐ d 6 ): δ (ppm): 164.35, 148.81, 147.82, 147.25, 133.80, 128.09, 127.84, 123.59, 118.15, 115.14, 114.84, 66.23. LC–MS: m / z calcd for C 14 H 11 N 3 O 3 [M + H] + : 269.26, found: 270.30.…”

Section: Methodsmentioning

confidence: 99%

“…2‐(3‐Nitrophenyl)‐2,3‐dihydoquinazolin‐4(1 H )‐one (Table 2, product entry 3b, Figures S5–S8) Yellow solid, M.P‐188–190°C 41–43 ; IR (KBr) cm −1 : 3295, 3191, 3073, 2372, 2318, 1653, 1608, 1533, 1483, 1392; 1 H NMR (400 MHz, DMSO‐ d 6 ): δ (ppm): 8.32–8.33 (q, J = 4 Hz, 2H), 8.07–8.10 (m, 1H), 7.84–7.89 (m, J = 8 Hz, 1H), 7.60–7.62 (m, J = 8 Hz, 1H), 7.51–7.55 (t, J = 8 Hz, 1H), 7.15–7.19 (m, 1H), 6.98 (s, 1H), 6.70–6.72 (d, J = 8 Hz, 1H), 6.61–6.65 (t, J = 8 Hz, 1H) 5.84 (d, J = 2 Hz, 1H); 13 C NMR (100 MHz, DMSO‐ d 6 ): δ (ppm): 164.25, 148.13, 147.41, 144.30, 133.84, 133.40, 129.86, 127.80, 123.38, 121.97, 118, 115.15, 114.92, 65.88. LC–MS: m / z calcd for C 14 H 11 N 3 O 3 [M + H] + : 270.29.…”

Section: Methodsmentioning

confidence: 99%

“…2-(4-Nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one (Table 2, product entry 3a, Figures S1-S4) Yellow solid, M.P-200-202 C [41][42][43]…”

Section: Spectroscopic Data Of Synthesized Compoundsmentioning

confidence: 99%

“…M.P-178 C41,42 ; IR (KBr) cm À1 : 3239, 2851, 1616, 1514, 1258, 1016; 1 H NMR (400 MHz, CDCl 3 ): δ (ppm): 7.81-7.83(s, 1H), 7.43-7.46 (t, J = 8, 2H), 7.22-7.26 (m, 2H), 6.80-6.88 (d, 2H), 6.76-6.80 (t, 1H), 6.62-6.64 (d, 1H), 6.05 (s, 1H), 5.76-5.77 (d, 1H), 3.74-3.76 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ (ppm): 178.92, 165.0, 161.79, 160.85, 147[M + H] + : 254.11, found: 254. 2-(2-Chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one (…”

mentioning

confidence: 99%

“…) White solid, M.P-202 C[41][42][43] ; IR (KBr) cm À1 : 3361, 3193, 2923, 2372, 1645, 1613, 1502;1 H NMR (400 MHz, DMSO-d 6 ) δ (ppm): 8.21 (br. s., 1H), 7.63 (d, J = 7.8 Hz, 1H), 7.51-7.60 (m, 1H), 7.42-7.49 (m, 1H), 7.30-7.41 (m, 2H), 7.26 (t, J = 7.7 Hz, 1H), 6.99 (s, 1H), 6.67-6.78 (m, 2H), 6.11 (s, 1H); 13 C NMR (101 MHz, DMSO-d 6 ): δ (ppm): 164.6, 147.9, 138.2, 134.4, 132.2, 130.9, 130.2, 128.8, 127.9, 118.2, 115.1, 114.8, 64.0.…”

mentioning

confidence: 99%

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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

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%

Section: Methodsmentioning

confidence: 99%

“…2-(4-Nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one (Table 2, product entry 3a, Figures S1-S4) Yellow solid, M.P-200-202 C [41][42][43]…”

Section: Spectroscopic Data Of Synthesized Compoundsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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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

Gurav

Gurav²,

Zond

et al. 2023

Applied Organom Chemis

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Small Organic Molecule‐Assisted Mesoscopic Self‐Assembly of SnO₂ Nanoparticles: An Efficient Catalyst for the Synthesis of β‐Nitroaldol

Das,

Abdul Matheen,

Kathiravan

et al. 2024

ChemCatChem

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A large number of mesoporous materials have been synthesized by using supramolecular assembly of ionic/non‐ionic surfactants as structure‐directing agents (SDAs). Here, we report a facile synthetic strategy to fabricate self‐assembled SnO2 nanoparticles with well‐defined nanocrystalline spherical morphology and mesoporosity using sodium salicylate as a SDA and stabilizing agent. The mesophases of the materials were investigated by powder XRD, TEM and N2 sorption studies. TEM results show that the mesopores are formed by the assembly of ultrasmall SnO2 NPs with broad range of interparticle void spaces. This synthesis strategy facilitated the generation of SnO2 NPs with increased surface area and pores of nanoscale dimensions with a large number of exposed surface active sites. The photoinduced electron transfer in these materials was investigated by the fluorescence quenching study with pyranine, which suggested the presence of surface Lewis basicity. The materials showed excellent catalytic activity for the synthesis of β‐nitroaldol through the reaction of benzaldehyde and nitromethane. The heterogeneous nature of the catalyst could be attributed to the high surface area, presence of numerous surface active sites, and structural robustness of the self‐assembled SnO2 nanostructure. The catalysts exhibited negligible loss in activity after several catalytic cycles.

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Nanoparticle Supported Bronsted Acidic Ionic Liquid Catalyzed Synthesis of Dihydro-1H-pyrazolylnaphthalene-1,4-diones

Chandane¹,

Gajare

Patil

et al. 2022

Catal Lett

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Sulfated tin oxide (SO4−2/SnO2): an efficient heterogeneous solid superacid catalyst for the facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones

Cited by 9 publications

References 59 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

Small Organic Molecule‐Assisted Mesoscopic Self‐Assembly of SnO₂ Nanoparticles: An Efficient Catalyst for the Synthesis of β‐Nitroaldol

Nanoparticle Supported Bronsted Acidic Ionic Liquid Catalyzed Synthesis of Dihydro-1H-pyrazolylnaphthalene-1,4-diones

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Sulfated tin oxide (SO4−2/SnO2): an efficient heterogeneous solid superacid catalyst for the facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones

Cited by 9 publications

References 59 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

Small Organic Molecule‐Assisted Mesoscopic Self‐Assembly of SnO2 Nanoparticles: An Efficient Catalyst for the Synthesis of β‐Nitroaldol

Nanoparticle Supported Bronsted Acidic Ionic Liquid Catalyzed Synthesis of Dihydro-1H-pyrazolylnaphthalene-1,4-diones

Contact Info

Product

Resources

About

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

Small Organic Molecule‐Assisted Mesoscopic Self‐Assembly of SnO₂ Nanoparticles: An Efficient Catalyst for the Synthesis of β‐Nitroaldol