Citation: Chen Liang, Wang Baoqu, Zhao Yucheng, Yan Shengjiao, Lin Jun. One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1433-1442. doi: 10.6023/cjoc201612038 shu

One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science andTechnology, Yunnan University, Kunming 650091

Corresponding author: Yan Shengjiao, yansj@ynu.edu.cn Lin Jun, linjun@ynu.edu.cn
Received Date: 12 December 2016
Revised Date: 21 January 2017

Fund Project: the National Natural Science Foundation of China U1202221the Talent Found in Yunnan Province 2012HB001the National Natural Science Foundation of China 21362042the National Natural Science Foundation of China 21662042the National Natural Science Foundation of China 21262042the Excellent Young Talents of Yunnan University XT412003

Figures(1)

A concise and environment friendly route for the synthesis of multisubstituted chromone-fused bicyclic pyridine compounds via one-step reaction of chromone-3-carboxaldehyde 1 and N-benzyl nitro ketene aminals (NBNKAs, 2) in ethanol media has been developed. The targeted compounds 3 can efficiently obtain by filter without extra post-treatment. The reaction is particularly attractive due to following features: low-cost and biocompatibility solvent, mild temperature, atom economy, high yields, and potential biological activity.
- environment friendly,
- atom economy,
- catalyst-free,
- bicyclic pyridine,
- neonicotinoids
1. [1]
  Hunt, A. J.; Sin, E. H. K.; Marriott, R.; Clark, J. H. CHemSusChem 2010, 3, 306. doi: 10.1002/cssc.200900169
2. [2]
  Agana, B. A.; Reeve, D.; Orbell, J. D. J Environ. Manage. 2013, 114, 445. doi: 10.1016/j.jenvman.2012.10.047
3. [3]
  Marr, P. C.; Marr, A. C. Green Chem. 2016, 18, 105. doi: 10.1039/C5GC02277K
4. [4]
  Marteel-Parrish, A. E. J. Chem. Educ. 2014, 91, 1084. doi: 10.1021/ed400393b
5. [5]
  Trost, B. M. Science 1991, 254, 1471. doi: 10.1126/science.1962206
6. [6]
  Misono, M. Yuki Gosei Kagaku Kyokaishi 2003, 61, 406. doi: 10.5059/yukigoseikyokaishi.61.406
7. [7]
  Hartman, G. J.; Jin, Q. Z.; Collins, G. J.; Lee, K. N.; Ho, C. T.; Chang, S. S. J. Agric. Food Chem. 1983, 31, 1030. doi: 10.1021/jf00119a027
8. [8]
  Ren, T.; Liu, W.; Xue, Q.; Wang, H. Lubr. Sci. 1993, 5, 205. doi: 10.1002/(ISSN)1557-6833
9. [9]
  Ueda, Y.; Connolly, T. P.; Kadow, J. F.; Meanwell, N. A.; Wang, T.; Chen, C.-P. H.; Yeung, K.-S.; Zhang, Z.; Leahy, D. K.; Pack, S. K.; Soundararajan, N.; Sirard, P.; Levesque, K.; Thoraval, D. US 20050209246, 2005[Chem. Abstr. 2005, 143, 306343].
10. [10]
  Garuti, L.; Roberti, M.; Pizzirani, D. Mini-Rev. Med. Chem. 2007, 7, 481. doi: 10.2174/138955707780619626
11. [11]
  Schultz, C.; Link, A.; Leost, M.; Zaharevitz, D. W.; Gussio, R.; Sausville, E. A.; Meijer, L.; Kunick, C. J. Med. Chem. 1999, 42, 2909. doi: 10.1021/jm9900570
12. [12]
  Pluta, K.; Morak-Mlodawska, B.; Jelen, M. Eur. J. Med. Chem. 2011, 46, 3179. doi: 10.1016/j.ejmech.2011.05.013
13. [13]
  Sujatha, K.; Shanmugam, P.; Perumal, P. T.; Muralidharan, D.; Rajendran, M. Bioorg. Med. Chem. Lett. 2006, 16, 4893. doi: 10.1016/j.bmcl.2006.06.059
14. [14]
  Helal, C. J.; Kang, Z.; Hou, X.; Pandit, J.; Chappie, T. A.; Humphrey, J. M.; Marr, E. S.; Fennell, K. F.; Chenard, L. K.; Fox, C.; Schmidt, C. J.; Williams, R. D.; Chapin, D. S.; Siuciak, J.; Lebel, L.; Menniti, F.; Cianfrogna, J.; Fonseca, K. R.; Nelson, F. R.; O'Connor, R.; MacDougall, M.; McDowell, L.; Liras, S. J. Med. Chem. 2011, 54, 4536. doi: 10.1021/jm2001508
15. [15]
  Kim, I. Y.; Kim, S. H. KR 2016006050, 2016[Chem. Abstr. 2016, 164, 225869].
16. [16]
  Lhassani, M.; Chavignon, O.; Chezal, J.-M.; Teulade, J.-C.; Chapat, J.-P.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Gueiffier, A. Eur. J. Med. Chem. 1999, 34, 271. doi: 10.1016/S0223-5234(99)80061-0
17. [17]
  Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernandez, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290. doi: 10.1021/ja0423769
18. [18]
  Mizushige, K.; Ueda, T.; Yukiiri, K.; Suzuki, H. Cardiovasc. Drug Rev. 2002, 20, 163.
19. [19]
  Ankley, G. T.; Kahl, M. D.; Jensen, K. M.; Hornung, M. W.; Korte, J. J.; Makynen, E. A.; Leino, R. L. Toxicol. Sci. 2002, 67, 121. doi: 10.1093/toxsci/67.1.121
20. [20]
  Veber, D. F.; Johnson, S. R.; Cheng, H.-Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. J. Med. Chem. 2002, 45, 2615. doi: 10.1021/jm020017n
21. [21]
  Bai, D.; Lummis, S. C. R.; Leicht, W.; Breer, H.; Sattelle, D. B. Pestic. Sci. 1991, 33, 197. doi: 10.1002/ps.v33:2
22. [22]
  Feng, X.-G.; Liu, X.-W.; Han, Z.-L.; Guan, L.-T.; Xu, L.-Z. J. Qingdao Univ. Sci. Technol., Nat. Sci. Ed. 2012, 33, 381.
23. [23]
  Li, J.; Huang, T.; Li, L.; Ding, T.; Zhu, H.; Yang, B.; Ye, Q.; Gan, J. J. Agric. Food Chem. 2016, 64, 8109. doi: 10.1021/acs.jafc.6b03422
24. [24]
  Tomizawa, M.; Casida, J. E. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 247. doi: 10.1146/annurev.pharmtox.45.120403.095930
25. [25]
  Bao, H.; Shao, X.; Zhang, Y.; Deng, Y.; Xu, X.; Liu, Z.; Li, Z. J. Agric. Food Chem. 2016, 64, 5148. doi: 10.1021/acs.jafc.6b01512
26. [26]
  Lu, S.; Zhuang, Y.; Wu, N.; Feng, Y.; Cheng, J.; Li, Z.; Chen, J.; Yuan, J.; Xu, X. J. Agric. Food Chem. 2013, 61, 10858. doi: 10.1021/jf403272h
27. [27]
  Shao, X.; Xu, Z.; Zhao, X.; Xu, X.; Tao, L.; Li, Z.; Qian, X. J. Agric. Food Chem. 2010, 58, 2690. doi: 10.1021/jf902513t
28. [28]
  (a) Huang, Z.; Wang, M. Heterocycles 1994, 37, 1233.
  (b) Kong, L.; Yang, R.; Du, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2016, 36, 2437 (in Chinese).
  (孔令斌, 杨瑞霞, 杜璇璇, 严胜骄, 林军, 有机化学, 2016, 36, 2437.)
  (c) Peng, M.; Yang, R.; Liu, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2015, 35, 1754 (in Chinese).
  (彭美阳, 杨瑞霞, 刘昔敏, 严胜骄, 林军, 有机化学, 2015, 35, 1754.)
29. [29]
  (a) Chen, X.-B.; Liu, Z.-C.; Lin, X.-R.; Huang, R.; Yan, S.-J.; Lin, J. ACS Sustainable Chem. Eng. 2014, 2, 2391.
  (b) Luo, D.; Cui, S.; Hu, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2017, 37, 166 (in Chinese).
  (罗大云, 崔时胜, 胡兴梅, 林军, 严胜骄, 有机化学, 2017, 37, 166.)
30. [30]
  Yu, F.-C.; Huang, R.; Ni, H.; Fan, J.; Yan, S.-J.; Lin, J. Green Chem. 2013, 15, 453. doi: 10.1039/C2GC36552A
31. [31]
  Chen, X.-B.; Liu, Z.-C.; Yang, L.-F.; Yan, S.-J.; Lin, J. ACS Sustainable Chem. Eng. 2014, 2, 1155. doi: 10.1021/sc500170d
32. [32]
  Xiao, X.; Wang, X.; Gui, X.; Chen, L.; Huang, B. Chem. Biodiversity 2016, 11, 1427.
33. [33]
  Mir, S. A. Int. J. PharmTech Res. 2016, 9, 70.
34. [34]
  (a) Ding, Z.-W.; Tan, Q.-T.; Liu, B.-X.; Xu, K.; Xu, B. Acta Chim. Sinica 2015, 73, 1302 (in Chinese).
  (丁正伟, 谭启涛, 刘秉新, 张可, 许斌, 化学学报, 2015, 73, 1302.)
  (b) Zhao, J.-B.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235 (in Chinese).
  (赵金钵, 张前, 化学学报, 2015, 73, 1235.)
35. [35]
  Alizadeh, A.; Bayat, F.; Zhu, Z. Res. Chem. Intermed. 2016, 42, 5927. doi: 10.1007/s11164-015-2414-6
36. [36]
  Yaqub, M.; Perveen, R.; Shafiq, Z.; Pervez, H.; Tahir, M. N. Synlett 2012, 23, 1755. doi: 10.1055/s-00000083
37. [37]
  Nishiwaki, H.; Nakagawa, Y.; Takeda, D. Y.; Okazawa, A.; Akamatsu, M.; Miyagawa, H.; Ueno, T.; Nishimura, K. Pest Manage. Sci. 2000, 56, 875. doi: 10.1002/(ISSN)1526-4998
1. [1]
  Jing Wang , Pingping Li , Yuehui Wang , Yifan Xiu , Bingqian Zhang , Shuwen Wang , Hongtao Gao . Treatment and Discharge Evaluation of Phosphorus-Containing Wastewater. University Chemistry, 2024, 39(5): 52-62. doi: 10.3866/PKU.DXHX202309097
2. [2]
  Yang WANG , Xiaoqin ZHENG , Yang LIU , Kai ZHANG , Jiahui KOU , Linbing SUN . Mn single-atom catalysts based on confined space: Fabrication and the electrocatalytic oxygen evolution reaction performance. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2175-2185. doi: 10.11862/CJIC.20240165
3. [3]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
4. [4]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
5. [5]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
6. [6]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
7. [7]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
8. [8]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
9. [9]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
10. [10]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
11. [11]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
12. [12]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
13. [13]
  Asif Hassan Raza , Shumail Farhan , Zhixian Yu , Yan Wu . 用于高效制氢的双S型ZnS/ZnO/CdS异质结构光催化剂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406020-. doi: 10.3866/PKU.WHXB202406020
14. [14]
  Qingqing SHEN , Xiangbowen DU , Kaicheng QIAN , Zhikang JIN , Zheng FANG , Tong WEI , Renhong LI . Self-supporting Cu/α-FeOOH/foam nickel composite catalyst for efficient hydrogen production by coupling methanol oxidation and water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1953-1964. doi: 10.11862/CJIC.20240028
15. [15]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
16. [16]
  Shuang Yang , Qun Wang , Caiqin Miao , Ziqi Geng , Xinran Li , Yang Li , Xiaohong Wu . Ideological and Political Education Design for Research-Oriented Experimental Course of Highly Efficient Hydrogen Production from Water Electrolysis in Aerospace Perspective. University Chemistry, 2024, 39(11): 269-277. doi: 10.12461/PKU.DXHX202403044
17. [17]
  Yulian Hu , Xin Zhou , Xiaojun Han . A Virtual Simulation Experiment on the Design and Property Analysis of CO₂ Reduction Photocatalyst. University Chemistry, 2025, 40(3): 30-35. doi: 10.12461/PKU.DXHX202403088
18. [18]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
19. [19]
  Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO₂ reduction performance of Z-scheme Ag-Cu₂O/BiVO₄ photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434
20. [20]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1292)
HTML views(108)

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