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

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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).
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