10.1007/s40097-019-0298-5

Exploration of catalytic performance of nano-La2O3 as an efficient catalyst for dihydropyrimidinone/thione synthesis and gas sensing

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  • Vishnu Ashok Adole*1,
  • Thansing Bhavsing Pawar1,
  • Prashant Bhimrao Koli1,
  • Bapu Sonu Jagdale1,
  1. Research Centre in Chemistry and PG Department of Chemistry, Loknete Vyankatrao Hiray Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University Pune), Nashik, Maharashtra, 422003, IN
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Published in Issue 12-02-2019

How to Cite

Adole, V. A., Pawar, T. B., Koli, P. B., & Jagdale, B. S. (2019). Exploration of catalytic performance of nano-La2O3 as an efficient catalyst for dihydropyrimidinone/thione synthesis and gas sensing. Journal of Nanostructure in Chemistry, 9(1 (March 2019). https://doi.org/10.1007/s40097-019-0298-5
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Abstract

Abstract In the present work, we report an proficient, elegant, and rapid one-pot synthesis of variety of 3,4-dihydropyrimidine-2(1 H )-one/thione derivatives from β-dicarbonyl compounds, urea/thiourea, and various aromatic aldehydes using nano-La 2 O 3 catalyst under ultrasonic irradiation. This novel synthetic strategy benefits with excellent yields, short reaction time, benign reaction conditions, clean transformation, and purification of products by non-chromatographic strategies. In addition, the synthesized nano-material was also explored as an effective gas sensor for NO 2 , LPG, methyl alcohol, and ammonia. The gas-sensing properties such as selectivity and sensitivity of selected gases along with response and recovery for nano-La 2 O 3 sensor are reported in this paper. In this way, conferring nano-La 2 O 3 is a multifunctional catalyst not only for organic synthesis but also for gas sensing. The synthesized La 2 O 3 nano-material was characterized by Fourier transform IR, powder X-ray diffraction, field-emission scanning electron microscopy, high-resolution transmission electron microscopy, energy-dispersive spectroscopy, and Brunauer–Emmett–Teller isotherm. The formation of Biginelli adducts was confirmed by Fourier transform IR, 1 HNMR, 13 CNMR, DEPT-135 (distortionless enhancement by polarization transfer spectra), and mass spectral techniques. Graphical abstract

Keywords

  • Nano-La2O3 catalyst,
  • 3,4-Dihydropyrimidine-2(1H)-ones/thiones,
  • Ultrasonic irradiation,
  • Gas sensing and BET
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References

  1. Schauermann et al. (2013) Nanoparticles for heterogeneous catalysis: new mechanistic insights 46(8) (pp. 1673-1681) https://doi.org/10.1021/ar300225s
  2. Chaturvedi et al. (2012) Applications of nano-catalyst in new era (pp. 307-325) https://doi.org/10.1016/j.jscs.2011.01.015
  3. Shan et al. (2009) Applications of nanomaterials in environmental science and engineering: review (pp. 110-119) https://doi.org/10.1061/(ASCE)1090-025X(2009)13:2(110)
  4. Sharma et al. (2015) Preparation and catalytic applications of nanomaterials: a review (pp. 53381-53403) https://doi.org/10.1039/C5RA06778B
  5. Astruc et al. (2015) Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis (pp. 7852-7872) https://doi.org/10.1002/anie.200500766
  6. Xu et al. (2018) Nanomaterial-based gas sensors: a review (pp. 115-145) https://doi.org/10.1080/10739149.2017.1340896
  7. Datsan et al. (2012) Environmentally benign synthesis of heterocyclic compounds by combined microwave-assisted heterogeneous catalytic approaches (pp. 17-37) https://doi.org/10.1039/C1GC15837F
  8. Kassaee et al. (2010) An efficient one-pot solvent-free synthesis of 2,3-dihydroquinazoline-4(1H)-ones via Al/Al2O3 nanoparticles (pp. 1421-1424) https://doi.org/10.1002/jhet.506
  9. Maleki et al. (2017) One-pot synthesis of 1,4-dihydropyridine derivatives catalyzed by silica-coated magnetic NiFe2O4 nanoparticles-supported H14[NaP5W30O110] (pp. 2922-2929) https://doi.org/10.1134/S1070363217120325
  10. Draye and Kardos (2016) Advances in green organic sonochemistry https://doi.org/10.1007/s41061-016-0074-7
  11. Atwal et al. (1990) Dihydropyrimidine calcium channel blockers: 2-heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5- pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines 33(9) (pp. 1510-1515) https://doi.org/10.1021/jm00167a035
  12. Kim et al. (2012) Discovery of 3,4-dihydropyrimidin-2(1H)-ones with inhibitory activity against HIV-1 replication 22(5) (pp. 2119-2124) https://doi.org/10.1016/j.bmcl.2011.12.090
  13. Mansouri et al. (2012) Synthesis and antioxidant evaluation of 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate esters 7(4) (pp. 257-264)
  14. Kumar et al. (2009) Novel Biginelli dihydropyrimidines with potential anticancer activity: a parallel synthesis and CoMSIA study 44(10) (pp. 4192-4198) https://doi.org/10.1016/j.ejmech.2009.05.014
  15. Yadlapalli et al. (2012) Synthesis and in vitro anticancer and antitubercular activity of diarylpyrazole ligated dihydropyrimidines possessing lipophilic carbamoyl group 22(8) (pp. 2708-2711) https://doi.org/10.1016/j.bmcl.2012.02.101
  16. Sharma et al. (2004) Synthesis and QSAR studies of pyrimido[4,5 d]pyrimidine-2,5-dione derivatives as potential antimicrobial agents (pp. 4185-4190) https://doi.org/10.1016/j.bmcl.2004.06.014
  17. Trivedi et al. (2010) Novel dihydropyrimidines as a potential new class of antitubercular agents 20(20) (pp. 6100-6102) https://doi.org/10.1016/j.bmcl.2010.08.046
  18. Tale et al. (2011) The novel 3,4-dihydropyrimidin-2(1H)-one urea derivatives of N-aryl urea: synthesis, anti-inflammatory, antibacterial and antifungal activity evaluation (pp. 4648-4651) https://doi.org/10.1016/j.bmcl.2011.03.062
  19. Adibi et al. (2007) Iron(III) trifluoroacetate and trifluoromethanesulfonate: recyclable Lewis acid catalysts for one-pot synthesis of 3,4-dihydropyrimidinones or their sulfur analogues and 1,4-dihydropyridines via solvent-free Biginelli and Hantzsch condensation protocols (pp. 2119-2124) https://doi.org/10.1016/j.catcom.2007.04.022
  20. Hamper et al. (1999) Solid phase synthesis of dihydropyrimidinones and pyrimidinone carboxylie acids from malonic acid resin (pp. 4973-4976) https://doi.org/10.1016/S0040-4039(99)00961-2
  21. Fang et al. (2007) One-pot green procedure for Biginelli reaction catalyzed by novel task-specific room-temperature ionic liquids (pp. 208-211) https://doi.org/10.1016/j.molcata.2007.04.013
  22. Khabazzadeh et al. (2008) Microwave-assisted synthesis of dihydropyrimidin-2(1H)-ones using graphite supported lanthanum chloride as a mild and efficient catalyst (pp. 278-280) https://doi.org/10.1016/j.bmcl.2007.10.087
  23. Kamali et al. (2015) One-pot, solvent-free synthesis via Biginelli reaction: catalyst-free and new recyclable catalysts https://doi.org/10.1080/23312009.2015.1081667
  24. Auroux et al. (1996) Dehydration of 4-methylpentan-2-ol over lanthanum and cerium oxides (pp. 2619-2624) https://doi.org/10.1039/ft9969202619
  25. Liu et al. (2017) Facile shape-controlled synthesis of lanthanum oxide with different hierarchical micro/nanostructures for antibacterial activity based on phosphate removal (pp. 40965-40972) https://doi.org/10.1039/C7RA07521A
  26. Rao and Karthikeyan (2012) Removal of fluoride from water by adsorption onto lanthanum oxide (pp. 1101-1114) https://doi.org/10.1007/s11270-011-0928-0
  27. Vignolo et al. (2002) Structural and electrical properties of lanthanum oxide thin films deposited by laser ablation (pp. 522-526) https://doi.org/10.1016/S0169-4332(02)00329-X
  28. Qaroush et al. (2018) An efficient atom-economical chemoselective CO2 cycloaddition using lanthanum oxide/tetrabutyl ammonium bromide (pp. 1342-1349) https://doi.org/10.1039/C8SE00092A
  29. Pisecny et al. (2004) Growth of lanthanum oxide films for application as a gate dielectric in CMOS technology (pp. 231-236) https://doi.org/10.1016/j.mssp.2004.09.020
  30. Dey and Rai (2014) Yb3+ sensitized Er3+ doped La2O3 phosphor in temperature sensors and display devices (pp. 111-118) https://doi.org/10.1039/C3DT51773J
  31. Dey (2018) Semiconductor metal oxide gas sensors: a review (pp. 206-217) https://doi.org/10.1016/j.mseb.2017.12.036
  32. Fine et al. (2010) Metal oxide semi-conductor gas sensors in environmental monitoring (pp. 5469-5502) https://doi.org/10.3390/s100605469
  33. Wetchakuna et al. (2011) Semiconducting metal oxides as sensors for environmentally hazardous gases (pp. 580-591) https://doi.org/10.1016/j.snb.2011.08.032
  34. Gao et al. (2016) One-pot synthesis of La-doped SnO2 layered nanoarrays with enhanced gas-sensing performance toward acetone (pp. 10298-10310) https://doi.org/10.1039/C5RA27270J
  35. Nivolianitou et al. (2006) Statistical analysis of major accidents in petrochemical industry notified to the major accident reporting system (MARS) (pp. 1-7) https://doi.org/10.1016/j.jhazmat.2004.12.042
  36. Holt and Nickson (2018) Severe methanol poisoning with neurological sequelae: implications for diagnosis and management (pp. 335-339) https://doi.org/10.1111/imj.13725
  37. Pyatt (2003) Potential effects on human health of an ammonia rich atmospheric environment in an archaeologically important cave in Southeast Asia (pp. 986-988) https://doi.org/10.1136/oem.60.12.986
  38. Petit et al. (2017) The pathophysiology of nitrogen dioxide during inhaled nitric oxide therapy (pp. 7-13) https://doi.org/10.1097/MAT.0000000000000425
  39. Heravi et al. (2006) 12 Molybdophosphoric acid: a recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones (pp. 373-376) https://doi.org/10.1016/j.catcom.2005.12.007
  40. Pasunooti et al. (2011) A microwave-assisted, copper-catalyzed three-component synthesis of dihydropyrimidinones under mild conditions (pp. 80-84) https://doi.org/10.1016/j.tetlet.2010.10.150
  41. Debache et al. (2008) A one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base (pp. 6119-6121) https://doi.org/10.1016/j.tetlet.2008.08.016
  42. Silva et al. (2011) p-Sulfonic acid calixarenes as efficient and reusable organocatalysts for the synthesis of 3,4- dihydropyrimidin-2(1H)-ones/thiones (pp. 6328-6330) https://doi.org/10.1016/j.tetlet.2011.08.175
  43. Pourmousavi and Hasani (2011) H2SO4-Silica catalyzed one-pot and efficient synthesis of dihydropyrimidones under solvent-free conditions 8(S1) (pp. 462-466) https://doi.org/10.1155/2011/158612
  44. Bigdeli et al. (2007) Trichloroisocyanuric acid, a new and efficient catalyst for thesynthesis of dihydropyrimidinones (pp. 1641-1644) https://doi.org/10.1016/j.catcom.2007.01.022
  45. Quan et al. (2009) PS–PEG–SO3H as an efficient catalyst for 3,4-dihydropyrimidones via Biginelli reaction (pp. 1146-1148) https://doi.org/10.1016/j.catcom.2008.12.017
  46. Rong et al. (2018) Highly selective and sensitive methanol gas sensor based on molecular imprinted silver doped LaFeO3 core–shell and cage structures https://doi.org/10.1088/1361-6528/aaabd0
  47. Teeramongkonrasmee and Sriyudthsak (2000) Methanol and ammonia sensing characteristics of sol–gel derived thin film gas sensor (pp. 256-259) https://doi.org/10.1016/S0925-4005(00)00346-4
  48. Nechita et al. (2012) Ethanol and methanol sensing characteristics of Nb-doped TiO2 porous thin films 209(1) (pp. 153-159) https://doi.org/10.1002/pssa.201127057
  49. Koli et al. (2017) Methanol gas sensing properties of pervoskite LaFeO3 nanoparticles doped by transition metals Cr3+ and Co2+ 9(1) (pp. 253-259)
  50. Gao et al. (2017) General fabrication and enhanced VOC gas-sensing properties of hierarchically porous metal oxides (pp. 35897-35904) https://doi.org/10.1039/C7RA06808E
  51. Gao, Q., Zheng, W.T., Wei, C.D., Lin, H.M.: Methanol-sensing property improvement of mesostructured zinc oxide prepared by the nano casting strategy. J. Nanomater. 263852 (2013).
  52. https://doi.org/10.1155/2013/263852