Citation: Hossein Naeimi, Hossein Foroughi. Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions[J]. Chinese Journal of Catalysis, ;2015, 36(5): 734-741. doi: 10.1016/S1872-2067(14)60304-1 shu

Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions

Hossein Naeimi ^, ,
Hossein Foroughi

1.
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, Iran

Corresponding author: Hossein Naeimi,
Received Date: 22 December 2014
Available Online: 23 January 2015

A powerful and environmentally benign method has been developed for the one-pot synthesis of 4-substituted-1,5-benzodiazepines via the three-component reaction of a series of aldehydes with dimedone and o-phenylenediamine using [H-NMP][HSO₄] as a Brönsted acidic ionic liquid catalyst under solvent-free conditions. The key benefits of this new method over existing techniques include high yields, the use of a green catalyst, short reaction times and facile catalyst separation.
- Ionic liquid,
- Benzodiazepine,
- Solvent-free conditions,
- Dimedone
1. [1]
  [1] Shorter E. Benzodiazepines. A Historical Dictionary of Psychiatry. New York: Oxford University Press, 2005. 41
2. [2]
  [2] Bremner J B, Samosorn S. In: Newkome G R ed. Comprehensive Heterocyclic Chemistry III. Amsterdam: Elsevier, 2008
3. [3]
  [3] Riemann D, Perlis M L. Sleep Med Rev, 2009, 13: 205
4. [4]
  [4] Cortes E C, Cornejo A L, Garcia-Mellado de Cortes O. J Heterocycl Chem, 2007, 44: 183
5. [5]
  [5] Makaron L, Moran C A, Namjoshi O, Rallapalli S, Cook J M, Rowlett J K. Pharmacol Biochem Behav, 2013, 104: 62
6. [6]
  [6] Allison C, Pratt J A. Pharmacol Therapeut, 2003, 98: 171
7. [7]
  [7] Hawkins E J, Malte C A, Imel Z E, Saxon A J, Kivlahan D R. Drug Alcohol Depend, 2012, 124: 154
8. [8]
  [8] McGowan D, Nyanguile O, Cummings M D, Vendeville S, Vandyck K, Van-den Broeck W, Boutton C W, De Bondt H, Quirynen L, Amssoms K, Bonfanti J F, Last S, Rombauts K, Tahri A, Hu L L, Delouvroy F, Vermeiren K, Vandercruyssen G, Van der Helm L, Cleiren E, Mostmans W, Lory P, Pille G, Van Emelen K, Fanning G, Pauwels F, Lin T I, Simmen K, Raboisson P. Bioorg Med Chem Lett, 2009, 19: 2492
9. [9]
  [9] Schimer J, Cigler P, Vesely J, Grantz-Saskova K, Lepsik M, Brynda J, Rezacova P, Kozisek M, Cisarova I, Oberwinkler H, Kraeusslich H G, Konvalinka J. J Med Chem, 2012, 55: 10130
10. [10]
  [10] Fader L D, Bethell R, Bonneau P, Boes M, Bousquet Y, Cordingley M G, Coulombe R, Deroy P, Faucher A M, Gagnon A, Goudreau N, Grand-Maitre C, Guse I, Hucke O, Kawai S H, Lacoste J E, Landry S, Lemke C T, Malenfant E, Mason S, Morin S, O'Meara J, Simoneau B, Titolo S, Yoakim C. Bioorg Med Chem Lett, 2011, 21: 398
11. [11]
  [11] Leggio L, Kenna G A, Swift R M. Prog Neuro-Psychopharm Biol Psych, 2008, 32: 1106
12. [12]
  [12] Kodomari M, Noguchi T, Aoyama T. Synth Commun, 2004, 34: 1783
13. [13]
  [13] Maiti G, Kayal U, Karmakar R, Bhattacharya R N. Tetrahedron Lett, 2012, 53: 1460
14. [14]
  [14] Yi W B, Cai C. J Fluorine Chem, 2009, 130: 1054
15. [15]
  [15] Xu J X, Zuo G, Chan W L. Heteroatom Chem, 2001, 12: 636
16. [16]
  [16] Uchida H, Suzuki T, Mamo D C, Mulsant B H, Kikuchi T, Takeuchi H, Tomita M, Watanabe K, Yagi G, Kashima H. J Anxiety Disord, 2009, 23: 477
17. [17]
  [17] Leonard B E. Human Psychopharmacol, 1999, 14: 125
18. [18]
  [18] Holbrook A M, Crowther R, Lotter A, Cheng C, King D. Can Med Assoc J, 2000, 162: 225
19. [19]
  [19] Pan X Q, Zou J P, Huang Z H; Zhang W. Tetrahedron Lett, 2008, 49: 5302
20. [20]
  [20] Sangshetti J N, Chouthe R S, Jadhav M R, Sakle N S, Chabukswar A, Gonjari I, Darandale S, Shinde D B. Arab J Chem, 2013, doi:10.1016/j.arabjc.2013.04.004
21. [21]
  [21] Cortes E C, Banos M A, Garcia-Mellado De Cortes O. J Heterocycl Chem, 2004, 41: 277
22. [22]
  [22] Gurkovskii A L, Tonkikh N N, Petrova M V, Strakov A Y. Chem Heterocycl Compd, 1999, 35: 625
23. [23]
  [23] Strakov A Y, Petrova M V, Tonkikh N N, Gurkovskii A I, Popelis Y, Kreishman G P, Belyakov S V. Chem Heterocycl Compd, 1997, 33: 321
24. [24]
  [24] Tolpygin I E, Mikhailenko N V, Bumber A A, Shepelenko E N, Revinsky U V, Dubonosov A D, Bren V A, Minkin V I. Russ J Gen Chem, 2012, 82: 1243
25. [25]
  [25] Tonkikh N N, Strakovs A Y, Rizhanova K V, Petrova M V. Chem Heterocycl Compd, 2004, 40: 949
26. [26]
  [26] Jiang B, Li Q Y, Zhang H, Tu S J, Pindi S, Li G G. Org Lett, 2012, 14: 700
27. [27]
  [27] Wang S L, Cheng C, Wu F Y, Jiang B, Shi F, Tu S J, Rajale T, Li G G. Tetrahedron, 2011, 67: 4485
28. [28]
  [28] Zhu J P, Bienayme H. Multicomponent Reactions. Weinheim: Wiley-VCH, 2005
29. [29]
  [29] Kumaravel K, Vasuki G. Curr Org Chem, 2009, 13: 1820
30. [30]
  [30] Tietze L F, Bell H P, Brasche G. Domino Reactions in Organic Synthesis. Weinheim: Wiley-VCH, 2006
31. [31]
  [31] Terrett N K. Combinatorial Chemistry. New York: Oxford University Press, 1998
32. [32]
  [32] Chanda A, Fokin V V. Chem Rev, 2009, 109: 725
33. [33]
  [33] Pirrung M C, Das Sarma K. J Am Chem Soc, 2004, 126: 444
34. [34]
  [34] Dupont J, de Souza R F, Suarez P A Z. Chem Rev, 2002, 102: 3667
35. [35]
  [35] Itoh H, Naka K, Chujo Y. J Am Chem Soc, 2004: 126: 3026
36. [36]
  [36] Yue C B, Fang D, Liu L, Yi T F. J Mol Liq, 2011, 163: 99
37. [37]
  [37] Naeimi H, Nazifi Z S. C R Chim, 2014, 17: 41
38. [38]
  [38] Naeimi H, Nazifi Z S. J Ind Eng Chem, 2014, 20: 1043
39. [39]
  [39] Shaterian H R, Ranjbar M. J Mol Liq, 2011, 160: 40
40. [40]
  [40] Liu W W, Cheng L Y, Zhang Y M, Wang H P, Yu M F. J Mol Liq, 2008, 140: 68
41. [41]
  [41] Tong X L, Li Y D. ChemSusChem, 2010, 3: 350
42. [42]
  [42] Xie C X, Li H L, Li L, Yu S, Liu F S. J Hazard Mater, 2008, 151: 847
43. [43]
  [43] Arellano M del R, Martinez R, Cortes E. J Heterocycl Chem, 1982, 19: 321
1. [1]
  Tong Zhang , Xiaojing Liang , Licheng Wang , Shuai Wang , Xiaoxiao Liu , Yong Guo . An ionic liquid assisted hydrogel functionalized silica stationary phase for mixed-mode liquid chromatography. Chinese Chemical Letters, 2025, 36(1): 109889-. doi: 10.1016/j.cclet.2024.109889
2. [2]
  Aonan Wang , Jingwen Dai , Yiming Guo , Fanghua Ning , Xiaoyu Liu , Sidra Subhan , Jiaqian Qin , Shigang Lu , Jin Yi . Imidazolium bromide based dual-functional redox mediator for the construction of dendrite-free Li-CO₂ batteries. Chinese Chemical Letters, 2025, 36(7): 110186-. doi: 10.1016/j.cclet.2024.110186
3. [3]
  Boyuan Hu , Jian Zhang , Yulin Yang , Yayu Dong , Jiaqi Wang , Wei Wang , Kaifeng Lin , Debin Xia . Dual-functional POM@IL complex modulate hole transport layer properties and interfacial charge dynamics for highly efficient and stable perovskite solar cells. Chinese Chemical Letters, 2024, 35(7): 108933-. doi: 10.1016/j.cclet.2023.108933
4. [4]
  Jingjie Tang , Luying Xie , Jiayu Liu , Shangyu Shi , Xinyu Sun , Jiayang Lin , Qikun Yang , Chuan'ang Yu , Zecheng Wang , Yingying Wang , Zengyang Xie . Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University. University Chemistry, 2024, 39(3): 316-326. doi: 10.3866/PKU.DXHX202309091
5. [5]
  Yameen Ahmed , Xiangxiang Feng , Yuanji Gao , Yang Ding , Caoyu Long , Mustafa Haider , Hengyue Li , Zhuan Li , Shicheng Huang , Makhsud I. Saidaminov , Junliang Yang . Interface Modification by Ionic Liquid for Efficient and Stable FAPbI₃ Perovskite Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(6): 2303057-0. doi: 10.3866/PKU.WHXB202303057
6. [6]
  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
7. [7]
  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
8. [8]
  Jiajia Wang , XinXin Ge , Yajing Xiang , Xiaoliang Qi , Ying Li , Hangbin Xu , Erya Cai , Chaofan Zhang , Yulong Lan , Xiaojing Chen , Yizuo Shi , Zhangping Li , Jianliang Shen . An ionic liquid functionalized sericin hydrogel for drug-resistant bacteria-infected diabetic wound healing. Chinese Chemical Letters, 2025, 36(2): 109819-. doi: 10.1016/j.cclet.2024.109819
9. [9]
  Yuhao Zhou , Siyuan Wu , Xiaozhe Ren , Hongjin Li , Shu Li , Tianying Yan . Effects of salt fraction on the Na⁺ transport in salt-in-ionic liquid electrolytes. Chinese Chemical Letters, 2025, 36(6): 110048-. doi: 10.1016/j.cclet.2024.110048
10. [10]
  Mengyu Chen , Qinglin Zhou , Tianyun Qin , Ningyao Sun , Yuxi Chen , Yuwei Gong , Xingyi Li , Jinsong Liu . An ionic liquid-reinforced gelatin hydrogel with strong adhesion, antibacterial and anti-inflammatory properties for treating oral ulcers. Chinese Chemical Letters, 2025, 36(7): 110441-. doi: 10.1016/j.cclet.2024.110441
11. [11]
  Luyu Zhang , Zirong Dong , Shuai Yu , Guangyue Li , Weiwen Kong , Wenjuan Liu , Haisheng He , Yi Lu , Wei Wu , Jianping Qi . Ionic liquid-based in situ dynamically self-assembled cationic lipid nanocomplexes (CLNs) for enhanced intranasal siRNA delivery. Chinese Chemical Letters, 2024, 35(7): 109101-. doi: 10.1016/j.cclet.2023.109101
12. [12]
  Qiangwei Wang , Huijiao Liu , Mengjie Wang , Haojie Zhang , Jianda Xie , Xuanwei Hu , Shiming Zhou , Weitai Wu . Observation of high ionic conductivity of polyelectrolyte microgels in salt-free solutions. Chinese Chemical Letters, 2024, 35(4): 108743-. doi: 10.1016/j.cclet.2023.108743
13. [13]
  Li-Ying Wang , Jun-Jie Yu , Shuai Wang , Yang Liu , Ke-Xian Song , Ji-Pan Yu , Li-Yong Yuan , Zhi-Rong Liu , Wei-Qun Shi . Pyridine-based ionic sp² carbon-conjugated covalent organic frameworks for selective extraction of Pu(Ⅳ) from high-level liquid waste. Chinese Chemical Letters, 2025, 36(8): 110706-. doi: 10.1016/j.cclet.2024.110706
14. [14]
  Yixia Zhang , Caili Xue , Yunpeng Zhang , Qi Zhang , Kai Zhang , Yulin Liu , Zhaohui Shan , Wu Qiu , Gang Chen , Na Li , Hulin Zhang , Jiang Zhao , Da-Peng Yang . Cocktail effect of ionic patch driven by triboelectric nanogenerator for diabetic wound healing. Chinese Chemical Letters, 2024, 35(8): 109196-. doi: 10.1016/j.cclet.2023.109196
15. [15]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
16. [16]
  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
17. [17]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747
18. [18]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
19. [19]
  Jingyu Shi , Xiaofeng Wu , Yutong Chen , Yi Zhang , Xiangyan Hou , Ruike Lv , Junwei Liu , Mengpei Jiang , Keke Huang , Shouhua Feng . Structure factors dictate the ionic conductivity and chemical stability for cubic garnet-based solid-state electrolyte. Chinese Chemical Letters, 2025, 36(5): 109938-. doi: 10.1016/j.cclet.2024.109938
20. [20]
  Hao Zhang , Hao Liu , Ke Huang , Qingxiu Xia , Hongjie Xiong , Xiaohui Liu , Hui Jiang , Xuemei Wang . Ionic exchange based intracellular self-assembly of pitaya-structured nanoparticles for tumor imaging. Chinese Chemical Letters, 2025, 36(6): 110281-. doi: 10.1016/j.cclet.2024.110281

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(548)
HTML views(25)

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