Fe3O4 nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[a]xanthen-11(12H)-ones

引用本文: Davood Habibi, Sharif Kaamyabi, Hasan Hazarkhani. Fe₃O₄nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[a]xanthen-11(12H)-ones[J]. 催化学报, 2015, 36(3): 362-366. doi: 10.1016/S1872-2067(14)60238-2 shu

Citation: Davood Habibi, Sharif Kaamyabi, Hasan Hazarkhani. Fe₃O₄nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[a]xanthen-11(12H)-ones[J]. Chinese Journal of Catalysis, 2015, 36(3): 362-366. doi: 10.1016/S1872-2067(14)60238-2 shu

Fe₃O₄nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[a]xanthen-11(12H)-ones

通讯作者: Davood Habibi

基金项目:
This work was supported by the Bu-Ali Sina University, Hamedan 6517838683, Iran.

摘要: A simple and efficient method for the synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[α]xanthen- 11(12)-one derivatives (DDBXs) was developed by the condensation reaction of various substituted aryl aldehydes with 2-naphthol and dimedone using Fe₃O₄ magnetic nanoparticles (MNPs) as a heterogeneous catalyst under solvent-free conditions at 90-110℃. The experimental procedure is very simple, the products are formed in high yields and the catalyst is easily separated by applying an external magnetic field.

关键词:

English

Fe₃O₄nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[a]xanthen-11(12H)-ones

1.
a Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran;

Corresponding author: Davood Habibi

Received Date: 12 August 2014
Available Online: 20 March 2015
Fund Project:
This work was supported by the Bu-Ali Sina University, Hamedan 6517838683, Iran.

Abstract: A simple and efficient method for the synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[α]xanthen- 11(12)-one derivatives (DDBXs) was developed by the condensation reaction of various substituted aryl aldehydes with 2-naphthol and dimedone using Fe₃O₄ magnetic nanoparticles (MNPs) as a heterogeneous catalyst under solvent-free conditions at 90-110℃. The experimental procedure is very simple, the products are formed in high yields and the catalyst is easily separated by applying an external magnetic field.

Key words:

1. [1] Hideo T. JP Patent 56005480A. 1981[1] Hideo T. JP Patent 56005480A. 1981
2. [2] Lambert R W, Martin J A, Merrett J H, Parkes K E B, Thomas G J. WO Patent 9706178 Al. 1997[2] Lambert R W, Martin J A, Merrett J H, Parkes K E B, Thomas G J. WO Patent 9706178 Al. 1997
3. [3] Ahmad M, King T A, Ko D K, Cha B H, Lee J. J Phys D Appl Phys, 2002, 35: 1473[3] Ahmad M, King T A, Ko D K, Cha B H, Lee J. J Phys D Appl Phys, 2002, 35: 1473
4. [4] Banerjee A, Mukherjee A K. Stain Technol, 1981, 56: 83[4] Banerjee A, Mukherjee A K. Stain Technol, 1981, 56: 83
5. [5] Knight C G, Stephens T. Biochem J, 1989, 258: 683[5] Knight C G, Stephens T. Biochem J, 1989, 258: 683
6. [6] Gao S, Tsai C H, Yao C F. Synlett, 2009: 949[6] Gao S, Tsai C H, Yao C F. Synlett, 2009: 949
7. [7] Mirjalili B F, Bamoniri A, Akbari A. Tetrahedron Lett, 2008, 49: 6454[7] Mirjalili B F, Bamoniri A, Akbari A. Tetrahedron Lett, 2008, 49: 6454
8. [8] Kumar A, Sharma S, Maurya R A, Sarkar J. J Comb Chem, 2010, 12: 20[8] Kumar A, Sharma S, Maurya R A, Sarkar J. J Comb Chem, 2010, 12: 20
9. [9] Zhang Z H, Zhang P, Yang S H, Wang H J, Deng J. J Chem Sci, 2010, 122: 427[9] Zhang Z H, Zhang P, Yang S H, Wang H J, Deng J. J Chem Sci, 2010, 122: 427
10. [10] Ghorbani-Vaghei R, M alaekepoor S M. Org Prep Proc Int, 2010, 42: 494[10] Ghorbani-Vaghei R, M alaekepoor S M. Org Prep Proc Int, 2010, 42: 494
11. [11] Nazeruddin G M, Al-Kadasi A M A. Res J Pharm Biol Chem Sci, 2011, 2: 71[11] Nazeruddin G M, Al-Kadasi A M A. Res J Pharm Biol Chem Sci, 2011, 2: 71
12. [12] Mo L P, Chen H L. J Chin Chem Soc (Taipei), 2010, 57: 157[12] Mo L P, Chen H L. J Chin Chem Soc (Taipei), 2010, 57: 157
13. [13] Nandi G C, Samai S, Kumar R, Singh M S. Tetrahedron, 2009, 65: 7129[13] Nandi G C, Samai S, Kumar R, Singh M S. Tetrahedron, 2009, 65: 7129
14. [14] Wang R Z, Zhang L F, Cui Z S. Synth Commun, 2009, 39: 2101[14] Wang R Z, Zhang L F, Cui Z S. Synth Commun, 2009, 39: 2101
15. [15] Das B, Laxminarayana K, Krishnaiah M, Srinivas Y. Synlett, 2007: 3107[15] Das B, Laxminarayana K, Krishnaiah M, Srinivas Y. Synlett, 2007: 3107
16. [16] Karimi N, Oskooie H A, Heravi M M, Tahershamsi L. Synth Commun, 2011, 41: 307[16] Karimi N, Oskooie H A, Heravi M M, Tahershamsi L. Synth Commun, 2011, 41: 307
17. [17] Li J J, Lu L M, Su W K. Tetrahedron Lett, 2010, 51: 2434[17] Li J J, Lu L M, Su W K. Tetrahedron Lett, 2010, 51: 2434
18. [18] Heravi M M, Alinejhad H, Bakhtiari K, Oskooie H A. Mol Divers, 2010, 14: 621[18] Heravi M M, Alinejhad H, Bakhtiari K, Oskooie H A. Mol Divers, 2010, 14: 621
19. [19] Li J J, Tang W Y, Lu L M, Su W K. Tetrahedron Lett, 2008, 49: 7117[19] Li J J, Tang W Y, Lu L M, Su W K. Tetrahedron Lett, 2008, 49: 7117
20. [20] Khurana J M, Magoo D. Tetrahedron Lett, 2009, 50: 4777[20] Khurana J M, Magoo D. Tetrahedron Lett, 2009, 50: 4777
21. [21] Wang H J, Ren X Q, Zhang Y Y, Zhang Z H. J Braz Chem Soc, 2009, 20: 1939[21] Wang H J, Ren X Q, Zhang Y Y, Zhang Z H. J Braz Chem Soc, 2009, 20: 1939
22. [22] Foroughifar N, Mobinikhaledi A, Moghanian H. Int J Green Nanotechnol, Phys Chem, 2009, 1: 57[22] Foroughifar N, Mobinikhaledi A, Moghanian H. Int J Green Nanotechnol, Phys Chem, 2009, 1: 57
23. [23] Shaterian H R, Yarahmadi H, Ghashang M. Tetrahedron, 2008, 64: 1263[23] Shaterian H R, Yarahmadi H, Ghashang M. Tetrahedron, 2008, 64: 1263
24. [24] Maschmeyer T, Rey F, Sankar G, Thomas J M. Nature, 1995, 378: 159[24] Maschmeyer T, Rey F, Sankar G, Thomas J M. Nature, 1995, 378: 159
25. [25] Rahimizadeh M, Bakhtiarpoor Z, Eshghi H, Pordel M, Rajabzadeh G. Monatsh Chem, 2009, 140: 1465[25] Rahimizadeh M, Bakhtiarpoor Z, Eshghi H, Pordel M, Rajabzadeh G. Monatsh Chem, 2009, 140: 1465
26. [26] Ballini R, Bordoni M, Bosica G, Maggi R, Sartori G. Tetrahedron Lett, 1998, 39: 7587[26] Ballini R, Bordoni M, Bosica G, Maggi R, Sartori G. Tetrahedron Lett, 1998, 39: 7587
27. [27] Zhang Z H, Lü H Y, Yang S H, Gao J W. J Comb Chem, 2010, 12: 643[27] Zhang Z H, Lü H Y, Yang S H, Gao J W. J Comb Chem, 2010, 12: 643
28. [28] Karami B, Hoseini S J, Eskandari Kh, Ghasemi A, Nasrabadi H. Catal Sci Technol, 2012, 2: 331[28] Karami B, Hoseini S J, Eskandari Kh, Ghasemi A, Nasrabadi H. Catal Sci Technol, 2012, 2: 331
29. [29] Ebrahimzadeh H, Moazzen E, Amini M M, Sadeghi O. Anal Methods, 2012, 4: 3232[29] Ebrahimzadeh H, Moazzen E, Amini M M, Sadeghi O. Anal Methods, 2012, 4: 3232
30. [30] Esmaeilpour M, Sardarian A R, Javidi J. Appl Catal A, 2012, 445-446: 359[30] Esmaeilpour M, Sardarian A R, Javidi J. Appl Catal A, 2012, 445-446: 359
31. [31] Rama V, Kanagaraj K, Pitchumani K. Tetrahedron Lett, 2012, 53: 1018[31] Rama V, Kanagaraj K, Pitchumani K. Tetrahedron Lett, 2012, 53: 1018
32. [32] Nandi G C, Samai S, Kumar R, Singh M S. Tetrahedron, 2009, 65: 7129[32] Nandi G C, Samai S, Kumar R, Singh M S. Tetrahedron, 2009, 65: 7129
33. [33] Tabatabaeian Kh, Khorshidi A, Mamaghani M, Dadashi A, Jalali M Kh. Can J Chem, 2011, 89: 623[33] Tabatabaeian Kh, Khorshidi A, Mamaghani M, Dadashi A, Jalali M Kh. Can J Chem, 2011, 89: 623
34. [34] Sun X J, Zhou J F, Zhao P S. J Heterocyclic Chem, 2011, 48: 1347[34] Sun X J, Zhou J F, Zhao P S. J Heterocyclic Chem, 2011, 48: 1347

扫一扫看文章

计量

PDF下载量: 223
文章访问数: 537
HTML全文浏览量: 10

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

Fe₃O₄nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[a]xanthen-11(12H)-ones

通讯作者: Davood Habibi

English

Fe₃O₄nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 9,9-dimethyl-9,10-dihydro-8H-benzo-[a]xanthen-11(12H)-ones

Corresponding author: Davood Habibi

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处