Citation: Wang Xiang, Chen Ping, Zhi Sanjun, Hu Huayou, Kan Yuhe, Zhang Zaichao. One-Pot Three-Component Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)chromen Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3299-3303. doi: 10.6023/cjoc201903032 shu

One-Pot Three-Component Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)chromen Derivatives

Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an, Jiangsu 223300

Corresponding author: Wang Xiang, hurricanwx@163.com Zhang Zaichao, zhangzc@hytc.edu.cn
Received Date: 17 March 2019
Revised Date: 21 May 2019
Available Online: 19 November 2019
Fund Project: the Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials JSKC15145the Department of Education of Jiangsu Province 16KJB150006the National Natural Science Foundation of China 51403073Project supported by the National Natural Science Foundation of China (Nos. 21601061, 51403073), the Department of Education of Jiangsu Province (No. 16KJB150006) and the Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials (No. JSKC15145)the National Natural Science Foundation of China 21601061

Figures(2)

Benzoimidazole and chromen derivatives exhibit a variety of important biological activities. Chromens incorporating benzoimidazole moiety have high Rho kinase inhibitory activity. However, the effective synthetic method for the preparation of these compounds is rare. The efficient synthesis of new substituted 3-(1H-benzo[d]imidazol-2-yl)-4H-chromens in 48%~89% yields via one-pot, three-component reaction of 2-(1H-benzo[d]imidazol-2-yl)acetonitrile with aromatic aldehydes and 5, 5-dimethylcyclohexane-1, 3-dione was studied. This reaction was carried out in EtOH in the presence of pyridine under reflux conditions. All reactions were completed within 1 to 3 h.
- benzoimidazole,
- chromen,
- multicomponent reaction,
- heterocyclic skeleton
1. [1]
  (a) Qiang, D. Z.; Shi, J. B.; Song, B. A.; Liu, X. H. RSC Adv. 2014, 4, 5607.
  (b) Sashidhara, K. V.; Rosaiah, J. N.; Bhatia, G.; Saxena, J. K. Eur. J. Med. Chem. 2008, 43, 2592.
  (c) Ding, X.; Xu, F. Chin. J. Org. Chem. 2018, 38, 3345 (in Chinese).
  (丁晓友, 徐凡, 有机化学, 2018, 38, 3345.
2. [2]
  (a) Akhtar, W.; Faraz Khan, M.; Verma, G.; Shaquiquzzaman, M.; Rizvib, M. A.; Hassan Mehdi, S.; Akhter, M.; Mumtaz Alam, M. Eur. J. Med. Chem. 2017, 126, 705.
  (b) Bansal, Y.; Silakari, O. Bioorg. Med. Chem. Lett. 2012, 20, 6208.
  (c) Yan, L.; Hou, Y.; Li, X.; Chen, H. Chin. J. Org. Chem. 2018, 38, 3332 (in Chinese).
  (闫连海, 侯宇恒, 李小六, 陈华, 有机化学, 2018, 38, 3332.)
  (d) Zhang, Z.; Zheng, X.; Guo, C. Chin. J. Org. Chem. 2016, 36, 1241 (in Chinese).
  (张钊瑞, 郑晓霖, 郭长彬, 有机化学, 2016, 36, 1241.)
  (e) Cheng, Z.; Zhang, Q. F.; Xu, X. L.; Li, X. N. Chin. J. Org. Chem. 2015, 35, 1189 (in Chinese).
  (程正, 张群峰, 许孝良, 李小年, 有机化学, 2015, 35, 1189.
3. [3]
  (a) Sessions, E. H.; Yin, Y.; Bannister, T. D.; Weiser, A.; Griffin, E.; Pocas, J.; Cameron, M. D.; Ruiz, C.; Lin, L.; Schürer, S. C.; Schröter, T.; LoGrasso, P.; Feng, Y. Bioorg. Med. Chem. Lett. 2008, 18, 6390.
  (b) Sessions, E. H.; Smolinski, M.; Wang, B.; Frackowiak, B.; Chowdhury, S.; Yin, Y.; Chen, Y. T.; Ruiz, C.; Lin, L.; Pocas, J.; Schröter, T.; Cameron, M. D.; LoGrasso, P.; Feng, Y.; Bannister, T. D. Bioorg. Med. Chem. Lett. 2010, 20, 1939.
4. [4]
  (a) Cioc, R. C.; Ruijter, E.; Orru, R. V. A. Green Chem. 2014, 16, 2958.
  (b) Sunderhaus, J. D.; Dockendorff, C.; Martin, S. F. Org. Lett. 2007, 9, 4223.
  (c) Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083.
5. [5]
  Fadda, A. A.; Youssif, E. H. E. Synth. Commun. 2011, 41, 677. doi: 10.1080/00397911003632915
6. [6]
  Wang, X.; Chen, P.; Zhi, S.; Hu, H.; Kan, Y. Chin. J. Org. Chem. 2018, 38, 3123 (in Chinese).
1. [1]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
2. [2]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
3. [3]
  Bin HE , Hao ZHANG , Lin XU , Yanghe LIU , Feifan LANG , Jiandong PANG . Recent progress in multicomponent zirconium?based metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2041-2062. doi: 10.11862/CJIC.20240161
4. [4]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.
5. [5]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
6. [6]
  Yanting HUANG , Hua XIANG , Mei PAN . Construction and application of multi-component systems based on luminous copper nanoclusters. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2075-2090. doi: 10.11862/CJIC.20240196
7. [7]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
8. [8]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
9. [9]
  Yue Zhang , Bao Li , Lixin Wu . GO-Assisted Supramolecular Framework Membrane for High-Performance Separation of Nanosized Oil-in-Water Emulsions. Acta Physico-Chimica Sinica, 2024, 40(5): 2305038-0. doi: 10.3866/PKU.WHXB202305038
10. [10]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
11. [11]
  Ruoqian Zhang , Chaoqun Mu , Yali Hou , Mingming Zhang . 四苯乙烯基多组分金属有机笼的构筑及其固态发光性能研究. University Chemistry, 2025, 40(8): 277-283. doi: 10.12461/PKU.DXHX202410027
12. [12]
  Wuxin Bai , Qianqian Zhou , Zhenjie Lu , Ye Song , Yongsheng Fu . Co-Ni Bimetallic Zeolitic Imidazolate Frameworks Supported on Carbon Cloth as Free-Standing Electrode for Highly Efficient Oxygen Evolution. Acta Physico-Chimica Sinica, 2024, 40(3): 2305041-0. doi: 10.3866/PKU.WHXB202305041
13. [13]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
14. [14]
  Weicheng Feng , Jingcheng Yu , Yilan Yang , Yige Guo , Geng Zou , Xiaoju Liu , Zhou Chen , Kun Dong , Yuefeng Song , Guoxiong Wang , Xinhe Bao . Regulating the High Entropy Component of Double Perovskite for High-Temperature Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(6): 2306013-0. doi: 10.3866/PKU.WHXB202306013
15. [15]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
16. [16]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
17. [17]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
18. [18]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
19. [19]
  Chaolin Mi , Yuying Qin , Xinli Huang , Yijie Luo , Zhiwei Zhang , Chengxiang Wang , Yuanchang Shi , Longwei Yin , Rutao Wang . Galvanic Replacement Synthesis of Graphene Coupled Amorphous Antimony Nanoparticles for High-Performance Sodium-Ion Capacitor. Acta Physico-Chimica Sinica, 2024, 40(5): 2306011-0. doi: 10.3866/PKU.WHXB202306011
20. [20]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(970)
HTML views(103)

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