Citation: Xue Li, Cheng-Hua Xu, Chuan-Qi Liu, Yu Chen, Jian-Ying Liu. Synthesis of pyrazinyl compounds from glycerol and 1,2-propanediamine over Cu-TiO₂ catalysts supported on γ-Al₂O₃[J]. Chinese Chemical Letters, ;2013, 24(8): 751-754. shu

Synthesis of pyrazinyl compounds from glycerol and 1,2-propanediamine over Cu-TiO₂ catalysts supported on γ-Al₂O₃

Xue Li ^a ,
Cheng-Hua Xu ^a,, ,
Chuan-Qi Liu ^a,b ,
Yu Chen ^a ,
Jian-Ying Liu ^a

1.
a Air Environmental Modeling and Pollution Controlling Key Laboratory of Sichuan Higher Education Institutes, Chengdu University of Information Technology, Chengdu 610225, China;
2.
b College of Optoelectronic Technology, Chengdu University of Information Technology, Chengdu 610225, China

Corresponding author: Cheng-Hua Xu,
Received Date: 26 February 2013
Available Online: 3 April 2013

Cu-TiO₂ catalysts supported on γ-Al₂O₃ are prepared and used in glycerol cyclization with 1,2-propanediamine to produce pyrazinyl compounds including 6-hydroxymethyl-2-methylpyrazine, 5-hydroxymethyl-2-methylpyrazine, 2,6-dimethylpyrazine and 2,5-dimethylpyrazine in a fixed-bed system. It is found that glycerol cylclization with 1,2-propanediamine gave a high total yield of pyrazinyl compounds (>80%) over Cu-TiO₂/γ-Al₂O₃ catalyst, and cyclization was through the reactions between activated 1,2-propanediamine and the intermediates from glycerol dehydration and oxidation. In addition, the regioselectivity of the pyrazinyl compounds was mainly controlled by the steric hindrance of the substrates during the cyclization process.
- Catalytic cyclization,
- Glycerol,
- Alkyl-substituted pyrazines,
- Steric effect
1. [1]
  [1] J. Basak, N. Hardia, S. Saxena, et al., Vapor-phase catalytic synthesis of 2-methylpyrazine over a nanocrystalline ferrite catalyst, Ind. Eng. Chem. Res. 46 (2007) 7039-7044.
2. [2]
  [2] F.L. Jing, W. Chu, Y.Y. Zhang, Y.Q. Chen, S.Z. Luo, Synthesis of 2-methylpyrazine from cyclocondensation of ethylene diamine and propyele glycol over promoted copper catalyst, Chin. Chem. Lett. 19 (2008) 752-755.
3. [3]
  [3] I. Park, J.H. Lee, Y.Y. Rhee, Y.H. Han, H.R. Kim, CuO/ZnO/SiO₂ catalysts for cyclization of propyleneglycol with ethylenediamine to 2-methylpyrazine, Appl. Catal. A 253 (2003) 249-255.
4. [4]
  [4] R. Sarkari, C. Anjaneyulu, V. Krishna, et al., Vapor phase synthesis of methylpyrazine using aqueous glycerol and ethylenediamine over ZnCr₂O₄ catalyst: elucidation of reaction mechanism, Catal. Commun. 12 (2011) 1067-1070.
5. [5]
  [5] C.Q. Liu, C.H. Xu, T.W. Xia, Y. Guo, J.Y. Liu, Glycerol catalytic cyclocondensation with ethanediamine to pyrazinyl compounds over the modified SiO₂-Al₂O₃, Heteroatom Chem. 23 (2012) 377-382.
6. [6]
  [6] C.H. Xu, L.K. Zheng, D.F. Deng, J.Y. Liu, S.Y. Liu, Effect of activation temperature on the surface copper particles and catalytic properties of Cu-Ni-Mγ-Al oxides from hydrotalcite-like precursors, Catal. Commun. 12 (2011) 996-999.
7. [7]
  [7] Z.L. Wang, Q.S. Liu, J.F. Yu, T.H. Wu, G.J. Wang, Surface structure and catalytic behavior of silica-supported copper catalysts prepared by impregnation and sol-gel methods, Appl. Catal. A 239 (2003) 87-94.
8. [8]
  [8] A. Ulgen, W.F. Hoelderich, Conversion of glycerol to acrolein in the presence of WO3/TiO₂ catalysts, Appl. Catal. A 400 (2011) 34-38.
9. [9]
  [9] M. Campanati, A. Vaccari, O. Piccolo, Environment-friendly synthesis of nitrogencontaining heterocyclic compounds, Catal. Today 60 (2000) 289-295.
10. [10]
  [10] J. Feng, J.B. Wang, Y.F. Zhou, et al., Effect of base additives on the selective hydrogenolysis of glycerol over Ru/TiO₂ catalyst, Chem. Lett. 36 (2007) 1274-1275.
1. [1]
  Min Fu , Pan He , Sen Zhou , Wenqiang Liu , Bo Ma , Shiying Shang , Yaohao Li , Ruihan Wang , Zhongping Tan . An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation. Chinese Chemical Letters, 2024, 35(8): 109434-. doi: 10.1016/j.cclet.2023.109434
2. [2]
  Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
3. [3]
  Jun-Yi Wang , Jue-Yu Bao , Zheng-Guang Wu , Zheng-Yin Du , Xunwen Xiao , Xu-Feng Luo . Recent progress in steric modulation of MR-TADF materials and doping concentration independent OLEDs with narrowband emission. Chinese Journal of Structural Chemistry, 2025, 44(1): 100451-100451. doi: 10.1016/j.cjsc.2024.100451
4. [4]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
5. [5]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
6. [6]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
7. [7]
  Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
8. [8]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
9. [9]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
10. [10]
  Jian Ji , Jie Yan , Honggen Peng . Modulation of dinuclear site by orbital coupling to boost catalytic performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100360-100360. doi: 10.1016/j.cjsc.2024.100360
11. [11]
  Zhenzhong MEI , Hongyu WANG , Xiuqi KANG , Yongliang SHAO , Jinzhong GU . Syntheses and catalytic performances of three coordination polymers with tetracarboxylate ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1795-1802. doi: 10.11862/CJIC.20240081
12. [12]
  Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411
13. [13]
  Yu Yao , Jinqiang Zhang , Yantao Wang , Kunsheng Hu , Yangyang Yang , Zhongshuai Zhu , Shuang Zhong , Huayang Zhang , Shaobin Wang , Xiaoguang Duan . Nitrogen-rich carbon for catalytic activation of peroxymonosulfate towards green synthesis. Chinese Chemical Letters, 2024, 35(11): 109633-. doi: 10.1016/j.cclet.2024.109633
14. [14]
  Rui HUANG , Shengjie LIU , Qingyuan WU , Nanfeng ZHENG . Enhanced selectivity of catalytic hydrogenation of halogenated nitroaromatics by interfacial effects. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 201-212. doi: 10.11862/CJIC.20240356
15. [15]
  Fanxin Kong , Hongzhi Wang , Huimei Duan . Inhibition effect of sulfation on Pt/TiO2 catalysts in methane combustion. Chinese Journal of Structural Chemistry, 2024, 43(5): 100287-100287. doi: 10.1016/j.cjsc.2024.100287
16. [16]
  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
17. [17]
  Yuan Dong , Mutian Ma , Zhenyang Jiao , Sheng Han , Likun Xiong , Zhao Deng , Yang Peng . Effect of electrolyte cation-mediated mechanism on electrocatalytic carbon dioxide reduction. Chinese Chemical Letters, 2024, 35(7): 109049-. doi: 10.1016/j.cclet.2023.109049
18. [18]
  Botao Gao , He Qi , Hui Liu , Jun Chen . Role of polarization evolution in the hysteresis effect of Pb-based antiferroelecrtics. Chinese Chemical Letters, 2024, 35(4): 108598-. doi: 10.1016/j.cclet.2023.108598
19. [19]
  Xin Huang , Yi Zhao , Wanzhen Liang . Vibronic coupling effect on intersystem crossing rates of TADF emitters. Chinese Journal of Structural Chemistry, 2024, 43(6): 100278-100278. doi: 10.1016/j.cjsc.2024.100278
20. [20]
  Cunjun Li , Wencong Liu , Xianlei Chen , Liang Li , Shenyu Lan , Mingshan Zhu . Adsorption and activation of peroxymonosulfate on BiOCl for carbamazepine degradation: The role of piezoelectric effect. Chinese Chemical Letters, 2024, 35(10): 109652-. doi: 10.1016/j.cclet.2024.109652

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(817)
HTML views(22)

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

Synthesis of pyrazinyl compounds from glycerol and 1,2-propanediamine over Cu-TiO2 catalysts supported on γ-Al2O3

Metrics

通讯作者: 陈斌, bchen63@163.com

Synthesis of pyrazinyl compounds from glycerol and 1,2-propanediamine over Cu-TiO₂ catalysts supported on γ-Al₂O₃