Citation: Abolghasem Davoodnia, Rahil Mahjoobin, Niloofar Tavakoli-Hoseini. A facile, green, one-pot synthesis of amidoalkyl naphthols under solvent-free conditions catalyzed by a carbon-based solid acid[J]. Chinese Journal of Catalysis, ;2014, 35(4): 490-495. doi: 10.1016/S1872-2067(14)60011-5 shu

A facile, green, one-pot synthesis of amidoalkyl naphthols under solvent-free conditions catalyzed by a carbon-based solid acid

1.
Department of Chemistry, Faculty of Sciences, Mashhad Branch, Islamic Azad University, Mashhad, Iran

Corresponding author: Abolghasem Davoodnia,
Received Date: 18 October 2013
Available Online: 25 December 2013

An efficient, environmentally friendly procedure for the synthesis of amidoalkyl naphthols through the one-pot, three-component reaction of β-naphthol, aryl aldehydes, and acetamide in the presence of a carbon-based solid acid under thermal solvent-free conditions is described. The beneficial features of this new synthetic approach include short reaction time, high yields, clean reaction profiles, and a simple work-up procedure. Furthermore, the catalyst can be readily recycled and reused four times without obvious significant loss of activity. The structure of the catalyst was confirmed by Fourier transform infrared spectroscopy, N₂ adsorption/desorption analysis, and X-ray diffraction.
- Amidoalkyl naphthol,
- Carbon-based solid acid,
- Heterogeneous catalysis,
- Solvent-free condition
1. [1]
  [1] Poliakoff M, Fitzpatrick J M, Farren T R, Anastas P T. Science, 2002, 297: 807
2. [2]
  [2] Khojastehnezhad A, Davoodnia A, Bakavoli M, Tavakoli-Hoseini N, Zeinali-Dastmalbaf M. Chin J Chem, 2011, 29: 297
3. [3]
  [3] Ugi I. Pure Appl Chem, 2001, 73: 187
4. [4]
  [4] Dömling A. Chem Rev, 2006, 106: 17
5. [5]
  [5] Davoodnia A, Heravi, M M, Safavi-Rad Z, Tavakoli-Hoseini N. Synth Commun, 2010, 40: 2588
6. [6]
  [6] Weber L. Drug Discov Today, 2002, 7: 143
7. [7]
  [7] Hulme C, Gore V. Curr Med Chem, 2003, 10: 51
8. [8]
  [8] Nagawade R R, Shinde D B. Mendeleev Commun, 2007, 17: 299
9. [9]
  [9] Das B, Laxminarayana K, Ravikanth B, Rao B R. J Mol Catal A, 2007, 261: 180
10. [10]
  [10] Nagarapu L, Baseeruddin M, Apuri S, Kantevari S. Catal Commun, 2007, 8: 1729
11. [11]
  [11] Nagawade R R, Shinde D B. Chin J Chem, 2007, 25: 1710
12. [12]
  [12] Lei M, Ma L, Hu L H. Tetrahedron Lett, 2009, 50: 6393
13. [13]
  [13] Kumar A, Rao M S, Ahmad I, Khungar B. Can J Chem, 2009, 87: 714
14. [14]
  [14] Jiang W Q, An L T, Zou J P. Chin J Chem, 2008, 26: 1697
15. [15]
  [15] Wang M, Liang Y. Monatsh Chem, 2011, 142: 153
16. [16]
  [16] Wang M, Liang Y, Zhang T T, Gao J J. Chin J Chem, 2011, 29: 1656
17. [17]
  [17] Shaterian H R, Yarahmadi H, Ghashang M. Bioorg Med Chem Lett, 2008, 18: 788
18. [18]
  [18] Shaterian H R, Yarahmadi H, Ghashang M. Tetrahedron, 2008, 64: 1263
19. [19]
  [19] Zali A, Shokrolahi A. Chin Chem Lett, 2012, 23: 269
20. [20]
  [20] Kantevari S, Vuppalapati S V N, Nagarapu L. Catal Commun, 2007, 8: 1857
21. [21]
  [21] Shaterian H R, Amirzadeh A, Khorami F, Ghashang M. Synth Commun, 2008, 38: 2983
22. [22]
  [22] Gerard V S, Notheisz F. Heterogeneous Catalysis in Organic Chemistry. San Diego: Elsevier, 2000
23. [23]
  [23] Wilson K, Clark J H. Pure Appl Chem, 2000, 72: 1313
24. [24]
  [24] Seifi N, Zahedi-Niaki M H, Barzegari M R, Davoodnia A, Zhiani R, Kaju A A. J Mol Catal A, 2006, 260: 77
25. [25]
  [25] Zeinali-Dastmalbaf M, Davoodnia A, Heravi M M, Tavakoli-Hoseini N, Khojastehnezhad A, Zamani H A. Bull Korean Chem Soc, 2011, 32: 656
26. [26]
  [26] Tanaka K, Toda F. Chem Rev, 2000, 100: 1025
27. [27]
  [27] Martins M A P, Frizzo C P, Moreira D N, Buriol L, Machado P. Chem Rev, 2009, 109: 4140
28. [28]
  [28] Davoodnia A, Heravi M M, Rezaei-Daghigh L, Tavakoli-Hoseini N. Monatsh Chem, 2009, 140: 1499
29. [29]
  [29] Davoodnia A, Bakavoli M, Moloudi R, Khashi M, Tavakoli-Hoseini N. Chin Chem Lett, 2010, 21: 1
30. [30]
  [30] Tavakoli-Hoseini N, Davoodnia A. Asian J Chem, 2010, 22: 7197
31. [31]
  [31] Davoodnia A, Khojastehnezhad A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 2243
32. [32]
  [32] Davoodnia A. Asian J Chem, 2010, 22: 1595
33. [33]
  [33] Davoodnia A. Synth React Inorg Met-Org Nano-Met Chem, 2012, 42: 1022
34. [34]
  [34] Mohammadzadeh-Dehsorkh N, Davoodnia A, Tavakoli-Hoseini N, Moghaddas M. Synth React Inorg Met-Org Nano-Met Chem, 2011, 41: 1135
35. [35]
  [35] Emrani A, Davoodnia A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 2385
36. [36]
  [36] Davoodnia A, Zare-Bidaki A, Behmadi H. Chin J Catal (催化学报), 2012, 33: 1797
37. [37]
  [37] Davoodnia A, Khashi M, Tavakoli-Hoseini N. Chin J Catal (催化学报), 2013, 34, 1173
38. [38]
  [38] Hara M, Yoshida T, Takagaki A, Takata T, Kondo J N, Hayashi S, Domen K. Angew Chem Int Ed, 2004, 43: 2955
39. [39]
  [39] Davoodnia A, Tavakoli-Nishaburi A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 635
40. [40]
  [40] Moghaddas M, Davoodnia A, Heravi M M, Tavakoli-Hoseini N. Chin J Catal, 2012, 33: 706
41. [41]
  [41] Tavakoli-Hoseini N, Davoodnia A. Chin J Chem, 2011, 29: 203
42. [42]
  [42] Sing K S W, Everett D H, Haul R A W, Moscou L, Pierotti R A, Rouquerol J, Siemieniewska T. Pure Appl Chem, 1985, 57: 603
1. [1]
  Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2024.100332
2. [2]
  Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
3. [3]
  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
4. [4]
  Chun Yin , Shuli Wang , Fulin Yang , Ligang Feng . Carbon-constrained heterogeneous Ni-Mo telluride for efficient urea oxidation. Chinese Chemical Letters, 2026, 37(6): 110999-. doi: 10.1016/j.cclet.2025.110999
5. [5]
  Tianyi Zhou , Heng Yang , Guangbin Zhou , Feng Chen , Pan Gao . Recent advances of heterogeneous manganese catalysis in organic synthesis. Chinese Chemical Letters, 2026, 37(6): 112223-. doi: 10.1016/j.cclet.2025.112223
6. [6]
  Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
7. [7]
  Shuai Tang , Zian Wang , Mengyi Zhu , Xinyun Zhao , Xiaoyun Hu , Hua Zhang . Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation. Chinese Chemical Letters, 2025, 36(5): 110503-. doi: 10.1016/j.cclet.2024.110503
8. [8]
  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
9. [9]
  Hua Liu , Jian Zhao , Qi Li , Xiang-Yu Zhang , Zhi-Wei Zheng , Kun Huang , Da-Bin Qin , Bin Zhao . Indium-captured zirconium-porphyrin frameworks displaying rare multi-selectivity for catalytic transfer hydrogenation of aldehydes and ketones. Chinese Chemical Letters, 2025, 36(6): 110593-. doi: 10.1016/j.cclet.2024.110593
10. [10]
  Shuangyu Wu , Jian Peng , Yue Jiang , Sijie Lin . The overlooked promotional effects of alcohols to BiOBr catalysts in photocatalytic degradation of organic pollutants. Chinese Chemical Letters, 2025, 36(11): 110819-. doi: 10.1016/j.cclet.2025.110819
11. [11]
  Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860
12. [12]
  Xinyuan Li , Zhuozhu Li , Wenzhong Huang , Jiantao Li , Wei Zhang , Shihao Feng , Hao Fan , Zhuo Chen , Sungsik Lee , Congcong Cai , Liang Zhou . Solvent-free synthesis of Co single atom and nanocluster decorated N-doped carbon for efficient oxygen reduction. Chinese Chemical Letters, 2025, 36(9): 110716-. doi: 10.1016/j.cclet.2024.110716
13. [13]
  Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
14. [14]
  Honghong Zhang , Zhen Wei , Derek Hao , Lin Jing , Yuxi Liu , Hongxing Dai , Weiqin Wei , Jiguang Deng . 非均相催化CO₂与烃类协同催化转化的最新进展. Acta Physico-Chimica Sinica, 2025, 41(7): 100073-0. doi: 10.1016/j.actphy.2025.100073
15. [15]
  Yongqing Xu , Yuyao Yang , Mengna Wu , Xiaoxiao Yang , Xuan Bie , Shiyu Zhang , Qinghai Li , Yanguo Zhang , Chenwei Zhang , Robert E. Przekop , Bogna Sztorch , Dariusz Brzakalski , Hui Zhou . Review on Using Molybdenum Carbides for the Thermal Catalysis of CO₂ Hydrogenation to Produce High-Value-Added Chemicals and Fuels. Acta Physico-Chimica Sinica, 2024, 40(4): 2304003-0. doi: 10.3866/PKU.WHXB202304003
16. [16]
  Fangyu Leng , Jian Zhang , Yuwen Zhang , Yuchun Jiang , Xiaohong Chang , Jie Wei . 以废治废：回收锌锰电池负极材料催化糖解PET塑料的综合实验教学. University Chemistry, 2026, 41(5): 319-329. doi: 10.12461/PKU.DXHX202510077
17. [17]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
18. [18]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
19. [19]
  Menglin Zhou , Lin Zhang , Xuefei Shan , Fengqin Chang , Wentong Chen , Xuguang An , Guangzhi Hu . Hydrangea-like B/N co-doped carbon-based electrochemical sensors for the efficient and sensitive detection of aristolochic acid in Aristolochia. Chinese Chemical Letters, 2025, 36(12): 111073-. doi: 10.1016/j.cclet.2025.111073
20. [20]
  Pengfu Gao , Yuan Geng , Wei Gong . Homochiral metal-organic frameworks bearing privileged ligands for heterogeneous asymmetric catalysis. Chinese Journal of Structural Chemistry, 2025, 44(10): 100719-100719. doi: 10.1016/j.cjsc.2025.100719

Get Citation

PDF

XML

Metrics

PDF Downloads(483)
Abstract views(1288)
HTML views(47)

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