Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst

doi:10.1016/S1872-2067(15)60845-2

催化学报 ›› 2015, Vol. 36 ›› Issue (8): 1379-1386.DOI: 10.1016/S1872-2067(15)60845-2

Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst

Marzieh Mohammadi^a, Ghasem Rezanejade Bardajee^b, Nader Noroozi Pesyan^a

a Department of Chemistry, Faculty of Science, Urmia University, 57159, Urmia, Iran;
b Department of Chemistry, Payame Noor University, P.O. BOX, 19395-3697, Tehran, Iran

收稿日期:2015-02-14 修回日期:2015-03-17 出版日期:2015-07-29 发布日期:2015-07-30
通讯作者: Ghasem Rezanejade Bardajee
基金资助:
This work was supported by Payame Noor University.

Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst

Marzieh Mohammadi^a, Ghasem Rezanejade Bardajee^b, Nader Noroozi Pesyan^a

a Department of Chemistry, Faculty of Science, Urmia University, 57159, Urmia, Iran;
b Department of Chemistry, Payame Noor University, P.O. BOX, 19395-3697, Tehran, Iran

Received:2015-02-14 Revised:2015-03-17 Online:2015-07-29 Published:2015-07-30
Supported by:
This work was supported by Payame Noor University.

摘要/Abstract

摘要：

A catalytic system comprising mesoporous silica functionalized with Cu(II)-DiAmSar was synthesized. This was demonstrated as an efficient heterogeneous catalyst for the synthesis of biologically useful pyridopyrazine and quinoxaline heterocycles under solvent-free conditions. X-ray diffraction, transmission electron microscopy, N₂ adsorption-desorption, Fourtier transformation infrared spectroscopy, and thermogravimetric analysis were used to characterize the catalyst and investigate the texture of SBA-15 during the grafting process.

关键词: DiAmSar, SBA-15, Heterogeneous catalyst, Pyridopyrazine, Quinoxaline

Abstract:

Key words: DiAmSar, SBA-15, Heterogeneous catalyst, Pyridopyrazine, Quinoxaline

Marzieh Mohammadi, Ghasem Rezanejade Bardajee, Nader Noroozi Pesyan. Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst[J]. 催化学报, 2015, 36(8): 1379-1386.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(15)60845-2

https://www.cjcatal.com/CN/Y2015/V36/I8/1379

参考文献

[1] Yadav J S, Reddy B V S, Premalatha K, Shankar K S. Synthesis, 2008: 3787
[2] He W, Myers M R, Hanney B, Spada A P, Bilder G, Galzcinski H, Amin D, Needle S, Page K, Jayyosi Z, Perrone M H. Bioorg Med Chem Lett, 2003, 13: 3097
[3] Escobar-Chavez J J, Merino V, Lopez-Cervantes M, Rodriguez-Cruz I M, Quintanar-Guerrero D, Ganem-Quintanar A. Curr Drug Discov Technol, 2009, 6: 171
[4] McLaughlin M A, Chiou G C Y. J Ocul Pharmacol, 1985, 1: 101
[5] Hugo W B, Stretton R G. Nature, 1964, 202: 1217
[6] Wu S H, Mou C Y, Lin H P. Chem Soc Rev, 2013, 42: 3862
[7] Conley M P, Copéret C, Thieuleux C. ACS Catal, 2014, 4: 1458
[8] Xie W L, Qi C. J Agr Food Chem, 2014, 62: 3348
[9] Xie W L, Hu L B, Yang X L. Ind Eng Chem Res, 2015, 54: 1505
[10] Xie W L, Zhao L L. Energy Convers Manage, 2014, 79: 34
[11] Meynen V, Cool P, Vansant E F. Microporous Mesoporous Mater, 2009, 125: 170
[12] Liu J, Liu Y, Yang W, Guo H, Zhang H Z, Tang Z H, Fang F. Mater Lett, 2014, 128: 15
[13] Shakeri M, Gebbink R J M K, de Jongh P E, de Jong K P. Microporous Mesoporous Mater, 2013, 170: 340
[14] Walcarius A, Mercier L. J Mater Chem, 2010, 20: 4478
[15] Yang Y, Zhang Y, Hao S J, Kan Q B. Chem Eng J, 2011, 171: 1356
[16] Coperet C, Chabanas M, Saint-Arroman R P, Basset J M. Angew Chem Int Ed, 2003, 42: 156
[17] Zou X C, Shi K Y, Wang C. Chin J Catal (邹晓川, 石开云, 王存. 催化学报), 2014, 35: 1446
[18] Zhu X C, Shen R W, Zhang L X. Chin J Catal (朱学成, 沈如伟, 张利雄. 催化学报), 2014, 35: 1716
[19] Malakooti R, Bardajee G R, Hadizadeh S, Atashin H, Khanjari H. Transit Metal Chem, 2014, 39: 47
[20] Motamedi R, Bardajee G R, Shakeri S. Heterocycl Commun, 2014, 20: 181
[21] Malakooti R, Bardajee G R, Mahmoudi H, Kakavand N. Catal Lett, 2013, 143: 853
[22] Bardajee G R, Malakooti R, Abtin I, Atashin H. Microporous Mesoporous Mater, 2013, 169: 67
[23] Bardajee G R, Malakooti R, Jami F, Parsaei Z, Atashin H. Catal Commun, 2012, 27: 49
[24] Mohammadi M, Bardajee G R,Pesyan N N. RSC Adv, 2014, 4: 62888
[25] Qin C J, James L, Chartres J D, Alcock L J, Davis K J, Willis A C, Sargeson A M, Bernhardt P V, Ralph S F. Inorg Chem, 2011, 50: 9131
[26] Geue R J, Hambley T W, Harrowfield J M, Sargeson A M, Snow M R. J Am Chem Soc, 1984, 106: 5478
[27] Di Bartolo N, Sargeson A M, Smith S V. Org Biomol Chem, 2006, 4: 3350
[28] Bell C A, Bernhardt P V, Gahan L R, Martinez M, Monteiro M J, Rodriguez C, Sharrad C A. Chem Eur J, 2010, 16: 3166
[29] Cai H, Fissekis J, Conti P S. Dalton Trans, 2009: 5395
[30] Hilderbrand S A, Weissleder R. Curr Opin Chem Biol, 2010, 14: 71
[31] Pathak K, Ahmad I, Abdi S H R, Kureshy R I, Khan N H, Jasra R V. J Mol Catal A, 2008, 280: 106
[32] Zhao D Y, Huo Q S, Feng J L, Chmelka B F, Stucky G D. J Am Chem Soc, 1998, 120: 6024
[33] Heravi M M, Tehrani M H, Bakhtiari K, Oskooie H A. Catal Commun, 2007, 8: 1341
[34] Darabi H R, Mohandessi S, Aghapoor K, Mohsenzadeh F. Catal Commun, 2007, 8: 389
[35] Aghapoor K, Darabi H R, Mohsenzadeh F, Balavar Y, Daneshyar H. Transit Metal Chem, 2010, 35: 49
[36] Antoine M, Czech M, Gerlach M, Günther E, Schuster T, Marchand P. Synthesis, 2011: 794
[37] Hasaninejad A, Zare A, Zolfigol M A, Shekouhy M. Synthetic Commun, 2009, 39: 569
[38] Heravi M M, Bakhtiari K, Oskooie H A, Taheri S. Heteroat Chem, 2008, 19: 218
[39] Khaksar S, Rostamnezhad F. Bull Korean Chem Soc, 2012, 33: 2581
[40] Huang T K, Wang R, Shi L, Lu X X. Catal Commun, 2008, 9: 1143
[41] Ahmad S, Ali M. Chin J Chem, 2007, 25: 818
[42] Darabi H R, Mohandessi S, Aghapoor K, Mohsenzadeh F. Catal Commun, 2007, 8: 389
[43] Go A, Lee G, Kim J, Bae S, Lee B M, Kim B H. Tetrahedron, 2015, 71: 1215

Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst

Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst

PDF

可视化

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics

[1]	楚庆岩, 陈静, 侯文华, 余昊轩, 王平, 刘睿, 宋广亮, 朱红军, 赵萍萍. 超声吸附制备均匀分散在SBA-15的S₂O₈^2--Fe₂O₃纳米粒子:增强S₂O₈^2--Fe₂O₃本体催化活性[J]. 催化学报, 2018, 39(5): 955-963.
[2]	沈行加, 吴先元, 江大好, 李小年, 倪珺. 利用原位红外光谱确证Ru/SBA-15的加氢活性位点[J]. 催化学报, 2017, 38(9): 1597-1602.
[3]	秦媛, 曲振平, 董翠, 黄娜. 预处理条件对Ag/SBA-15催化剂上甲苯催化氧化反应性能的影响[J]. 催化学报, 2017, 38(9): 1603-1612.
[4]	李冰, 徐振新, 储伟, 罗仕忠, 敬方梨. 有序介孔Sn-SBA-15负载铂催化剂上丙烷脱氢性能的提高[J]. 催化学报, 2017, 38(4): 726-735.
[5]	邹成龙, 沙观宇, 顾海芳, 黄曜, 牛国兴. 改善SBA-15介孔材料水热稳定性的简单溶剂热后处理方法[J]. 催化学报, 2015, 36(8): 1350-1357.
[6]	Sanjay Srivastava, Pravakar Mohanty, Jigisha K. Parikh, Ajay K. Dalai, S. S. Amritphale, Anup K. Khare. Cr-free Co-Cu/SBA-15 catalysts for hydrogenation of biomass-derived α-, β-unsaturated aldehyde to alcohol[J]. 催化学报, 2015, 36(7): 933-942.
[7]	Laxmikant D. Chavan, Sunil G. Shankarwar. KSF supported 10-molybdo-2-vanadophosphoric acid as an efficient and reusable catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazole derivatives under solvent-free condition[J]. 催化学报, 2015, 36(7): 1054-1059.
[8]	邹成龙, 沙观宇, 黄曜, 牛国兴, 赵东元. Al³⁺离子介入提升(NH₄)₂SiF₆对SBA-15介孔材料的水热稳定化作用[J]. 催化学报, 2015, 36(7): 1001-1008.
[9]	Kin Hong Liew, Wan Zurina Samad, Norazzizi Nordin, Poh Lee Loh, Joon Ching Juan, Mohd Ambar Yarmo, Badrul Hisham Yahaya, Rahimi M. Yusop. Preparation and characterization of HypoGel-supported Pd nanocatalysts for Suzuki reaction under mild conditions[J]. 催化学报, 2015, 36(5): 771-777.
[10]	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]. 催化学报, 2015, 36(4): 626-633.
[11]	Sara Sobhani, Farzaneh Zarifi. Pd-isatin Schiff base complex immobilized on γ-Fe₂O₃as a magnetically recyclable catalyst for the Heck and Suzuki cross-coupling reactions[J]. 催化学报, 2015, 36(4): 555-563.
[12]	王润琴, 林荣和, 丁云杰, 刘佳, 罗文婷, 杜虹, 吕元 . 水热合成一锅法制备FePO₄-SBA-15及其水热稳定性能[J]. 催化学报, 2015, 36(3): 446-453.
[13]	胡龙兴, 杨帆, 邹联沛, 袁航, 胡星. Co-Fe/SBA-15与过一硫酸盐联用非均相催化降解水中染料罗丹明B[J]. 催化学报, 2015, 36(10): 1785-1797.
[14]	刘会敏, 李宇明, 吴昊, 杨维维, 贺德华. Nd, Ce和La改性对Ni/SBA-15催化剂在CH₄/CO₂重整反应中性能的影响[J]. 催化学报, 2014, 35(9): 1520-1528.
[15]	Abdol R. Hajipour, Ghobad Azizi. Immobilized Pd nanoparticles on Tris-modified SiO₂：Synthesis, characterization, and catalytic activity in Heck cross-coupling reactions[J]. 催化学报, 2014, 35(9): 1547-1554.