Citation: Nasir Iravani, Mosadegh Keshavarz, Hossein Ali Shojaeian Kish, Rasool Parandvar. Tin sulfide nanoparticles supported on activated carbon as an efficient and reusable Lewis acid catalyst for three-component one-pot synthesis of 4H-pyrano[2, 3-c]pyrazole derivatives[J]. Chinese Journal of Catalysis, ;2015, 36(4): 626-633. doi: 10.1016/S1872-2067(14)60284-9 shu

Tin sulfide nanoparticles supported on activated carbon as an efficient and reusable Lewis acid catalyst for three-component one-pot synthesis of 4H-pyrano[2, 3-c]pyrazole derivatives

1.
a Department of Chemistry, Faculty of Science, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran;

Corresponding author: Nasir Iravani, Mosadegh Keshavarz,
Received Date: 13 November 2014
Available Online: 15 December 2014

Tin sulfide nanoparticles (SnS-NPs) were prepared in aqueous solution at room temperature on the surface of activated carbon (AC) and were investigated using field-emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), X-ray diffraction, reflective ultraviolet-visible spectrophotometry, and spectrofluorimetry. Calculations based on the SEM and TEM images showed that the sizes of the SnS-NPs immobilized on the AC were 30-70 nm. The prepared nanocomposite was used as a heterogeneous Lewis acid catalyst for the three-components one-pot synthesis of 4H-pyrano[2,3-c]pyrazole derivatives in ethanol at 80 ℃. The reactions were efficiently performed in the presence of the prepared catalyst in short reaction times, and gave the desired products in high yields. This catalyst can be easily recovered by simple filtration and recycled up to eight consecutive times without significant loss of its efficiency.
- Tin sulfide nanoparticle,
- Nanocomposite,
- Lewis acid catalyst,
- Heterogeneous catalyst,
- 4H-pyrano[2,3-c]pyrazole,
- Multicomponent reaction
1. [1]
  [1] Buzea C, Pacheco I I, Robbie K. Biointerphases, 2007, 2(4): MR17
2. [2]
  [2] Astruc D. Nanoparticles and Catalysis. Weinheim: Wiley-VCH, 2008
3. [3]
  [3] Tian N, Zhou Z Y, Yu N F, Wang L Y, Sun S G. J Am Chem Soc, 2010, 132: 7580
4. [4]
  [4] Zhang C, Kang Z H, Shen E H, Wang E B, Gao L, Luo F, Tian C G, Wang C L, Lan Y, Li J X, Cao X J. J Phys Chem B, 2006, 110: 184
5. [5]
  [5] Li Z H, Zeng J H, Li Y D. Small, 2007, 3: 438
6. [6]
  [6] Chen L J, Li L P, Li G S. J Alloys Compd, 2008, 464: 532
7. [7]
  [7] Cheng F Y, Shen J, Peng B, Pan Y D, Tao Z L, Chen J. Nat Chem, 2011, 3: 79
8. [8]
  [8] Xia Y N, Xiong Y J, Lim B, Skrabalak S E. Angew Chem Int Ed, 2009, 48: 60
9. [9]
  [9] Xiong Y J, Xia Y N. Adv Mater, 2007, 19: 3385
10. [10]
  [10] Kaneko K, Inoke K, Freitag B, Hungria A B, Midgley P A, Hansen T W, Zhang J, Ohara S, Adschiri T. Nano Lett, 2007, 7: 421
11. [11]
  [11] Wu Y, Wadia C, Ma W L, Sadtler B, Alivisatos A P. Nano Lett, 2008, 8: 2551
12. [12]
  [12] Choi S H, Kim E G, Hyeon T. J Am Chem Soc, 2006, 128: 2520
13. [13]
  [13] Camacho-Bragado G A, Elechiguerra J L, Yacaman M J. Mater Character, 2008, 59: 204
14. [14]
  [14] Pua F L, Chia C H, Zakaria S, Neoh S K, Liew T K. Sains Malaysiana, 2011, 40: 221
15. [15]
  [15] Zou J, Zhang J X, Zhang B H, Zhao P T, Huang K X. Mater Lett, 2007, 61: 5029
16. [16]
  [16] Ma L, Chen W X, Li H, Zheng Y F, Xu Z D. Mater Lett, 2008, 62: 797
17. [17]
  [17] Sun Y F, Cheng H, Gao S, Sun Z H, Liu Q H, Liu Q, Lei F C, Yao T, He J F, Wei S Q, Xie Y. Angew Chem Int Ed, 2012, 51: 8727
18. [18]
  [18] Dai P C, Zhang G, Chen Y C, Jiang H C, Feng Z Y, Lin Z J, Zhan J H. Chem Commun, 2012, 48: 3006
19. [19]
  [19] Ramasamy K, Malik M A, O'Brien P. Chem Commun, 2012, 48: 5703
20. [20]
  [20] Xin X K, He M, Han W, Jung J, Lin Z Q. Angew Chem Int Ed, 2011, 50: 11739
21. [21]
  [21] Kuo S C, Huang L J, Nakamura H. J Med Chem, 1984, 27: 539
22. [22]
  [22] Wang J L, Liu D X, Zhang Z J, Shan S M, Han X B, Srinivasula S M, Croce C M, Alnemri E S, Huang Z W. Proc Natl Acad Sci USA, 2000, 97: 7124
23. [23]
  [23] Zaki M E A, Soliman H A, Hiekal O A, Rashad A E Z. Zeit Naturforsch C, 2006, 61: 1
24. [24]
  [24] Zhu J P, Bienayme H (Eds). Multicomponent Reactions. Weinheim: Wiley-VCH, 2005
25. [25]
  [25] Balaskar R S, Gavade S N, Mane M S, Shingate B B, Shingare M S, Mane D V. Chin Chem Lett, 2010, 21: 1175
26. [26]
  [26] Mecadon H, Rohman M R, Kharbangar I, Laloo B M, Kharkongor I, Rajbangshi M, Myrboh B. Tetrahedron Lett, 2011, 52: 3228
27. [27]
  [27] Heravi M M, Ghods A, Derikvand F, Bakhtiari K, Bamoharram F F. J Iran Chem Soc, 2010, 7: 615
28. [28]
  [28] Vasuki G, Kumaravel K. Tetrahedron Lett, 2008, 49: 5636
29. [29]
  [29] Gogoi S, Zhao C G. Tetrahedron Lett, 2009, 50: 2252
30. [30]
  [30] Sheibani H, Babaie M. Synth Commun, 2010, 40: 257
31. [31]
  [31] Ziarani G M, Abbasi A, Badiei A, Aslani Z. E J Chem, 2011, 8: 293
32. [32]
  [32] Gao S, Tsai C H, Tseng C, Yao C F. Tetrahedron, 2008, 64: 9143
33. [33]
  [33] Fotouhi L, Heravi M M, Fatehi A, Bakhtiari K. Tetrahedron Lett, 2007, 48: 5379
34. [34]
  [34] Azarifar D, Khatami S M, Nejat-Yami R. J Chem Sci, 2014, 126: 95
35. [35]
  [35] Azarifar A, Nejat-Yami R, Al-Kobaisi M, Azarifar D. J Iran Chem Soc, 2013, 10: 439
36. [36]
  [36] Khaksar S, Rouhollahpour A, Talesh S M. J Fluorine Chem, 2012, 141:11
37. [37]
  [37] Heravi M M, Javanmardi N, Oskooei H A, Baghernejad B. GU J Sci, 2011, 24: 227
38. [38]
  [38] Shi D Q, Mou J, Zuang Q Y, Niu L H, Wu N, Wang X S. Synth Commun, 2004, 34: 4557
39. [39]
  [39] Jin T S, Zhao R Q, Li T S. Arkivoc, 2006, (xi): 176
40. [40]
  [40] Niknam K, Borazjani N, Rashidian R, Jamali A. Chin J Catal (催化学报), 2013, 34: 2245
41. [41]
  [41] Hasaninejad A, Golzar N, Beyrati M, Zare A, Doroodmand M M. J Mol Catal A, 2013, 372: 137
42. [42]
  [42] Hasaninejad A, Shekouhy M, Golzar N, Zare A, Doroodmand M M. Appl Catal A, 2011, 402: 11
43. [43]
  [43] Albadi J, Keshavarz M, Shirini F, Vafaee-nezhad M. Catal Commun, 2012, 27: 17
44. [44]
  [44] Albadi J, Keshavarz M, Abedini M, Khoshakhlagh M. J Chem Sci, 2013, 125: 295
45. [45]
  [45] Albadi J, Keshavarz M, Abedini M, Vafaee-nezhad M. Chin Chem Lett, 2012, 23: 797
46. [46]
  [46] Keshavarz M, Iravani N, Ghaedi A, Ahmady A Z, Vafaei-Nezhad M, Karimi S. SpringerPlus, 2013, 2: 64
47. [47]
  [47] Yavari I, Hajinasiri R, Sayyed-Alangi S Z, Iravani N. Monatsh Chem, 2008, 139: 1029
48. [48]
  [48] Yavari I, Sanaeishoar T, Ghazvini M, Iravani N. J Sulfur Chem, 2010, 31: 169
49. [49]
  [49] Iravani N, Safikhani Mohammadzade N, Niknam K. Chin Chem Lett, 2011, 22: 1151
50. [50]
  [50] Iravani N, Karami B, Asadimoghaddam F, Monfared M, Karami N. J Sulfur Chem, 2012, 33: 279
51. [51]
  [51] Iravani N, Albadi J, Varnaseri S, Jaberi Z, Karami N, Khadamati M. J Chin Chem Soc, 2012, 59: 1567
52. [52]
  [52] Iravani N, Keshavarz M, Monfared M, Hosseini F. J Chin Chem Soc, 2014, 61: 357
53. [53]
  [53] Nazari S, Keshavarz M, Karami B, Iravani N, Vafaee-Nezhad M. Chin Chem Lett, 2014, 25: 317
54. [54]
  [54] Koktysh D S, McBride J R, Rosenthal S J. Nanoscale Res Lett, 2007, 2: 144
55. [55]
  [55] Avellaneda D, Delgado G, Nair M T S, Nair P K. Thin Solid Films, 2007, 515: 5771
56. [56]
  [56] Goudarzi A, Motedayen Aval G, Sahraei R, Ahmadpoor H. Thin Solid Films, 2008, 516: 4953
1. [1]
  Jia-Cheng Hou , Hong-Tao Ji , Yu-Han Lu , Jia-Sheng Wang , Yao-Dan Xu , Yan-Yan Zeng , Wei-Min He . Sustainable and practical semi-heterogeneous photosynthesis of 5-amino-1,2,4-thiadiazoles over WS₂/TEMPO. Chinese Chemical Letters, 2024, 35(8): 109514-. doi: 10.1016/j.cclet.2024.109514
2. [2]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
3. [3]
  Fereshte Hassanzadeh-Afruzi , Mina Azizi , Iman Zare , Ehsan Nazarzadeh Zare , Anwarul Hasan , Siavash Iravani , Pooyan Makvandi , Yi Xu . Advanced metal-organic frameworks-polymer platforms for accelerated dermal wound healing. Chinese Chemical Letters, 2024, 35(11): 109564-. doi: 10.1016/j.cclet.2024.109564
4. [4]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
5. [5]
  Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
6. [6]
  Mengxiang Zhu , Tao Ding , Yunzhang Li , Yuanjie Peng , Ruiping Liu , Quan Zou , Leilei Yang , Shenglei Sun , Pin Zhou , Guosheng Shi , Dongting Yue . Graphene controlled solid-state growth of oxygen vacancies riched V₂O₅ catalyst to highly activate Fenton-like reaction. Chinese Chemical Letters, 2024, 35(12): 109833-. doi: 10.1016/j.cclet.2024.109833
7. [7]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
8. [8]
  Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H₄PMo₁₁VO₄₀ catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
9. [9]
  Xingang Kong , Yabei Su , Cuijuan Xing , Weijie Cheng , Jianfeng Huang , Lifeng Zhang , Haibo Ouyang , Qi Feng . Facile synthesis of porous TiO₂/SnO₂ nanocomposite as lithium ion battery anode with enhanced cycling stability via nanoconfinement effect. Chinese Chemical Letters, 2024, 35(11): 109428-. doi: 10.1016/j.cclet.2023.109428
10. [10]
  Peng Wang , Daijie Deng , Suqin Wu , Li Xu . Cobalt-based deep eutectic solvent modified nitrogen-doped carbon catalyst for boosting oxygen reduction reaction in zinc-air batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100199-100199. doi: 10.1016/j.cjsc.2023.100199
11. [11]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
12. [12]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
13. [13]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
14. [14]
  Yatian Deng , Dao Wang , Jinglan Cheng , Yunkun Zhao , Zongbao Li , Chunyan Zang , Jian Li , Lichao Jia . A new popular transition metal-based catalyst: SmMn₂O₅ mullite-type oxide. Chinese Chemical Letters, 2024, 35(8): 109141-. doi: 10.1016/j.cclet.2023.109141
15. [15]
  Yaoyin Lou , Xiaoyang Jerry Huang , Kuang-Min Zhao , Mark J. Douthwaite , Tingting Fan , Fa Lu , Ouardia Akdim , Na Tian , Shigang Sun , Graham J. Hutchings . Stable core-shell Janus BiAg bimetallic catalyst for CO₂ electrolysis into formate. Chinese Chemical Letters, 2025, 36(3): 110300-. doi: 10.1016/j.cclet.2024.110300
16. [16]
  Chaozheng He , Menghui Xi , Chenxu Zhao , Ran Wang , Ling Fu , Jinrong Huo . Highly N₂ dissociation catalyst: Ir(100) and Ir(110) surfaces. Chinese Chemical Letters, 2025, 36(3): 109671-. doi: 10.1016/j.cclet.2024.109671
17. [17]
  Hong Yin , Zhipeng Yu . Hexavalent iridium catalyst enhances efficiency of hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(1): 100382-100382. doi: 10.1016/j.cjsc.2024.100382
18. [18]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
19. [19]
  Yiwen Xu , Chaozheng He , Chenxu Zhao , Ling Fu . Single-atom Ti doping on S-vacancy two-dimensional CrS₂ as a catalyst for ammonia synthesis: A DFT study. Chinese Chemical Letters, 2025, 36(4): 109797-. doi: 10.1016/j.cclet.2024.109797
20. [20]
  Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe₂O₄@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(306)
HTML views(45)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142