Citation: You Liqin, Yuan Jinwei, Yang Liangru, Xiao Yongmei, Mao Pu. Progress in the Synthesis of 2-Aminobenzoxazole Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(11): 2634-2650. doi: 10.6023/cjoc201604044 shu

Progress in the Synthesis of 2-Aminobenzoxazole Derivatives

1.
Academician Workstation for Natural Medicinal Chemistry of Henan Province, School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001

Corresponding author: Yuan Jinwei, yuanjinweigs@126.com
Received Date: 21 April 2016
Revised Date: 28 May 2016

Fund Project: the Program for Innovative Research Team from Zhengzhou 131PCXTD605the National Natural Science Foundation of China 21302042the National Natural Science Foundation of China 21172055the Natural Science Foundation in Henan Province Department of Education 14B150053the Natural Science Foundation from Technology bureau of Zhengzhou City 20130883the Department of Henan Province Natural Science and Technology Foundation 142102210410

Figures(28)

2-Aminobenzoxazole derivatives are a kind of heterocyclic compounds, which play important roles in medicine, biology and material science, and their synthetic methods have attracted much attention. In recent years, many efficient, green synthetic approaches of 2-aminobenzoxazole derivatives using transition-metal or metal-free catalytic systems have been reported. Based on differences of reaction substrates and synthetic methods, the recent advances in the synthesis of 2-aminobenzoxazole derivatives are reviewed.
- 2-aminobenzoxazole,
- transition-metal catalyzed,
- metal-free catalyzed,
- synthesis,
- research progress
1. [1]
  Alper-Hayta, S.; Arisoy, M.; Temiz-Arpaci, Ö.; Yildiz, I.; Aki, E.; Özkan, S.; Kaynak, F. Eur. J. Med. Chem. 2008, 43, 2568. doi: 10.1016/j.ejmech.2007.12.019
2. [2]
  Safak, C.; Erdogan, H.; Palaska, E.; Sunal, R.; Duru, S. J. Med. Chem. 1992, 35, 1296. doi: 10.1021/jm00085a018
3. [3]
  Hal, I. H.; Peaty, N. J.; Henry, J. R.; Easmon, J.; Heinisch, G.; Pürstinger, G. Arch. Pharm. 1999, 332, 115. doi: 10.1002/(ISSN)1521-4184
4. [4]
  Ge, F.; Wang, Z.; Wan, W.; Lu, W.; Hao, J. Tetrahedron Lett. 2007, 48, 3251. doi: 10.1016/j.tetlet.2007.03.015
5. [5]
  Ren, P.; Salihu, I.; Scopelliti, R.; Hu, X. L. Org. Lett. 2012, 14, 1748. doi: 10.1021/ol300348w
6. [6]
  Wu, X. J.; See, J. W. T.; Xu, K.; Hirao, H.; Roger, J.; Hierso, J. C.; Zhou, J. R. Angew. Chem., Int. Ed. 2014, 53, 13573. doi: 10.1002/anie.201408355
7. [7]
  Yang, K.; Chen, X. Y.; Wang, Y. Q.; Li, W. Q.; Kadi, A. A.; Fun, H. K.; Sun, H.; Zhang, Y.; Li, G. G.; Lu, H. J. J. Org. Chem. 2015, 80, 11065. doi: 10.1021/acs.joc.5b01450
8. [8]
  Yang, K.; Zhang, C.; Wang, P.; Zhang, Y.; Ge, H. B. Chem. Eur. J. 2014, 20, 7241. doi: 10.1002/chem.201402516
9. [9]
  Wu, X. F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 7316. doi: 10.1002/anie.v49:40
10. [10]
  Huang, J. K.; Chan, J.; Chen, Y.; Borths, C. J.; Baucom, K. D.; Larsen, R. D. Faul, M. M. J. Am. Chem. Soc. 2010, 132, 3674. doi: 10.1021/ja100354j
11. [11]
  Zhu, F.; Wang, Z. X. Org. Lett. 2015, 17, 1601. doi: 10.1021/acs.orglett.5b00510
12. [12]
  Shibahara, F.; Yamaguchi, E.; Murai, T. Chem. Commun. 2010, 46, 2471. doi: 10.1039/b920794e
13. [13]
  Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 4156. doi: 10.1021/ol901684h
14. [14]
  Kim, S. H.; Yoon, J.; Chang, S. Org. Lett. 2011, 13, 1474. doi: 10.1021/ol200154s
15. [15]
  Parsharamulu, T.; Reddy, P. V.; Likhar, P. R.; Lakshmi, M. Tetrahedron 2015, 71, 1975. doi: 10.1016/j.tet.2015.02.020
16. [16]
  Hou, C. D.; Ren, Y. L.; Lang, R.; Hu, X. X.; Xia, C. G.; Li, F. W. Chem. Commun. 2012, 48, 5181. doi: 10.1039/c2cc30429e
17. [17]
  Kim, J. Y.; Cho, S. H.; Joseph, J.; Chang, S. Angew. Chem., Int. Ed. 2010, 49, 9899. doi: 10.1002/anie.v49.51
18. [18]
  Neyts, J.; De Clercq, E.; Singha, R.; Chang, Y. H.; Das, A. R.; Chakraborty, S. K.; Hong, S. C.; Tsay, S. C.; Hsu, M. H.; Hwu, J. R. J. Med. Chem. 2009, 52, 1486. doi: 10.1021/jm801240d
19. [19]
  Cox, C. D.; Breslin, M. J.; Whitman, D. B.; Schreier, J. D.; McGaughey, G. B.; Bogusky, M. J.; Roecker, A. J.; Mercer, S. P.; Bednar, R. A.; Lemaire, W.; Bruno, J. G.; Reiss, D. R.; Harrell, M.; Murphy, K. L.; Garson, S. L.; Doran, S. M.; Prueksaritanont, T.; Anderson, W. B.; Tang, C.; Roller, S.; Cabalu, T. D.; Cui, D. H.; Hartman, G. D.; Young, S. D.; Koblan, K. S.; Winrow, C. J.; Renger, J. J.; Coleman, P. J. J. Med. Chem. 2010, 53, 5320. doi: 10.1021/jm100541c
20. [20]
  Seregin, I.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173. doi: 10.1039/b606984n
21. [21]
  Xiao, L. W.; Gao, H. J.; Kong, J.; Liu, G. X.; Peng, X. X.; Wang, S. J. Chin. J. Org. Chem. 2014, 34, 1048. doi: 10.6023/cjoc201401030
22. [22]
  Kaupp, G.; Schmeyers, J.; Boy, J. Chem. Eur. J. 1998, 4, 2467. doi: 10.1002/(SICI)1521-3765(19981204)4:12<>1.0.CO;2-I
23. [23]
  Wu, Y. Q.; Limburg, D. C.; Wilkinson, D. E.; Hamilton, G. S. J. Heterocycl. Chem. 2003, 40, 191. doi: 10.1002/jhet.v40:1
24. [24]
  El-Faham, A.; Chebbo, M.; Abdul-Ghani, M.; Younes, G. Heterocycl. Chem. 2006, 43, 599. doi: 10.1002/jhet.v43:3
25. [25]
  Cioffi, C. L.; Lansing, J. J.; Yüksel, H. J. Org. Chem. 2010, 75, 7942. doi: 10.1021/jo1017052
26. [26]
  Carpenter, R. D.; Kurth, M. J. Nat. Protoc. 2010, 5, 1731. doi: 10.1038/nprot.2010.132
27. [27]
  Zhang, X. Y.; Jia, X. F.; Wang, J. J.; Fan, X. S. Green Chem. 2011, 13, 413. doi: 10.1039/C0GC00418A
28. [28]
  Guo, X. J.; Guo, Q.; Zhao, W.; Zhang, X. Y. J. Henan Normal Univ. (Nat. Sci. Ed. 2013, 41, 85 (in Chinese).
29. [29]
  Guntreddi, T.; Allam, B. K.; Singh, K. N. RSC Adv. 2013, 3, 9875. doi: 10.1039/c3ra41189c
30. [30]
  Kasthuri, M.; Sharath Babu, H.; Shiva Kumar, C.; Nagendra Kumar, P. V. Synlett 2015, 26, 897. doi: 10.1055/s-00000083
31. [31]
  Lin, C. C.; Hsieh, T. H.; Liao, P. Y.; Liao, Z. Y.; Chang, C. W.; Shih, Y. C.; Yeh, W. H.; Chien, T. C. Org. Lett. 2014, 16, 892. doi: 10.1021/ol403645y
32. [32]
  Naga Raju, G. N.; Prasanna, T. S. K. T. World J. Pharm. Sci. 2015, 4, 1082.
33. [33]
  Vardhan Reddy, K. H.; Anil Kumar, B. S. P.; Prakash Reddy, V.; Uday Kumar, R.; Nageswar, Y. V. D. RSC Adv. 2014, 4, 45579. doi: 10.1039/C4RA05447D
34. [34]
  Yamato, M.; Takeuchi, Y.; Hattori, K.; Hashigaki, K. Chem. Pharm. Bull. 1984, 32, 3053. doi: 10.1248/cpb.32.3053
35. [35]
  Saladino, R.; Crestini, C.; Occhionero, F.; Nicoletti, R. Synth. Commun. 1996, 26, 3241. doi: 10.1080/00397919608004633
36. [36]
  Kövér, J.; Tímár, T.; Tompa, J. Synthesis 1994, 1124.
37. [37]
  Kim, J. Y.; Cho, S. H.; Joseph, J.; Chang, S. Angew. Chem. 2010, 122, 10095. doi: 10.1002/ange.v122.51
38. [38]
  Gu, J.; Cai, C. Synlett 2015, 26, 639. doi: 10.1055/s-00000083
39. [39]
  Kim, J. Y.; Cho, S. H.; Joseph, J.; Chang, S. Angew. Chem., Int. Ed. 2010, 49, 9899. doi: 10.1002/anie.v49.51
40. [40]
  Li, Y. M.; Liu, J.; Xie, Y. S.; Zhang, R.; Jin, K.; Wang, X. N.; Duan, C. Y. Org. Biomol. Chem. 2012, 10, 3715. doi: 10.1039/c2ob25425e
41. [41]
  Cai, S. F.; He, W.; Li, Y. D.; Yu, X. F.; Zhang, Q.; Li, L. S. CN 102766108, 2012[Chem. Abstr. 2012, 157, 734720.]
42. [42]
  Li, Y. M.; Xie, Y. S.; Zhang, R.; Jin, K.; Wang, X. N.; Duan, C. Y. J. Org. Chem. 2011, 76, 5444. doi: 10.1021/jo200447x
43. [43]
  Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A. Org. Lett. 2009, 11, 1607. doi: 10.1021/ol900298e
44. [44]
  Mitsuda, S.; Fujiwara, T.; Kimigafukuro, K.; Monguchi, D.; Mori, A. Tetrahedron 2012, 68, 3585. doi: 10.1016/j.tet.2012.03.001
45. [45]
  Pal, P.; Giri, A. K.; Singh, H.; Ghosh, S. C.; Panda, A. B. Chem. Asian J. 2014, 9, 2392. doi: 10.1002/asia.201402057
46. [46]
  Xie, Y. J.; Qian, B.; Xie, P.; Huang, H. M. Adv. Synth. Catal. 2013, 355, 1315. doi: 10.1002/adsc.v355.7
47. [47]
  Cao, K.; Wang, J. L.; Wang, L. H.; Li, Y. Y.; Yu, X. H.; Huang, Y. W.; Yang, J. X.; Chang, G. J. Synth. Commun. 2014, 44, 2848. doi: 10.1080/00397911.2014.919402
48. [48]
  Lamani, M.; Prabhu, K. R. J. Org. Chem. 2011, 76, 7938. doi: 10.1021/jo201402a
49. [49]
  Froehr, T.; Sindlinger, C. P.; Kloeckner, U.; Finkbeiner, P.; Nachtsheim, B. J. Org. Lett. 2011, 13, 3754. doi: 10.1021/ol201439t
50. [50]
  Wagh, Y. S.; Sawant, D. N.; Bhanage, B. M. Tetrahedron Lett. 2012, 53, 3482. doi: 10.1016/j.tetlet.2012.04.117
51. [51]
  Gao, W. J.; Li, W. C.; Zeng, C. C.; Tian, H. Y.; Hu, L. M.; Little, R. D. J. Org. Chem. 2014, 79, 9613. doi: 10.1021/jo501736w
52. [52]
  Joseph, J.; Kim, J. Y.; Chang, S. Chem. Eur. J. 2011, 17, 8294. doi: 10.1002/chem.201100910
53. [53]
  Wertz, S.; Kodama, S.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 11511. doi: 10.1002/anie.v50.48
54. [54]
  Wagh, Y. S.; Tiwari, N. J.; Bhanage, B. M. Tetrahedron Lett. 2013, 54, 1290. doi: 10.1016/j.tetlet.2012.12.127
55. [55]
  Yotphan, S.; Beukeaw, D.; Reutrakul, V. Synthesis 2013, 45, 0936. doi: 10.1055/s-00000084
56. [56]
  Xu, D. Q.; Wang, W. F.; Miao, C. X.; Zhang, Q. H.; Xia, C. G.; Sun, W. Green Chem. 2013, 15, 2975. doi: 10.1039/c3gc41206g
57. [57]
  Wang, X. E.; Xu, D. Q.; Miao, C. X.; Zhang, Q. H.; Sun, W. Org. Biomol. Chem. 2014, 12, 3108. doi: 10.1039/c4ob00386a
58. [58]
  Maity, S.; Zhu, M.; Shinabery, R. S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 222. doi: 10.1002/anie.201106162
59. [59]
  Maity, S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 9562. doi: 10.1002/anie.v51.38
60. [60]
  Allen, L. J.; Cabrera, P. J.; Lee, M.; Sanford, M. S. J. Am. Chem. Soc. 2014, 136, 5607. doi: 10.1021/ja501906x
61. [61]
  Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 8679. doi: 10.1039/c1cc12907d
62. [62]
  Wang, J. D.; Liu, Y. X.; Xue, D.; Wang, C.; Xiao, J. L. Synlett 2014, 25, 2013. doi: 10.1055/s-00000083
63. [63]
  Guo, S. M.; Qian, B.; Xie, Y. J.; Xia, C. G.; Huang, H. M. Org. Lett. 2011, 13, 522. doi: 10.1021/ol1030298
64. [64]
  Yuan, J. W.; Jin, M.; Yin, Q. Y.; Mao, P.; Qu, L. B. Z. Naturforsch. 2016, 71b, 317.
65. [65]
  Wang, S.; Wang, J.; Guo, R.; Wang, G.; Chen, S. Y.; Yu, X. Q. Tetrahedron Lett. 2013, 54, 6233. doi: 10.1016/j.tetlet.2013.09.018
66. [66]
  Cho, S. H.; Kim, J. Y.; Lee, S. Y.; Chang, S. Angew. Chem., Int. Ed. 2009, 48, 9127. doi: 10.1002/anie.v48:48
67. [67]
  Wang, J.; Hou, J. T.; Wen, J.; Zhang, J.; Yu, J. Q. Chem. Commun. 2011, 47, 3652. doi: 10.1039/c0cc05811d
68. [68]
  Wang, R.; Liu, H.; Yue, L.; Zhang, X. K.; Tan, Q. Y.; Pan, R. L. Tetrahedron Lett. 2014, 55, 2233. doi: 10.1016/j.tetlet.2014.02.070
69. [69]
  Kawano, T.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2010, 132, 6900. doi: 10.1021/ja101939r
70. [70]
  Chen, S. Y.; Zheng, K.; Chen, F. Tetrahedron Lett. 2012, 53, 6297. doi: 10.1016/j.tetlet.2012.09.044
71. [71]
  Yotphan, S.; Beukeaw, D.; Reutrakul, V. Tetrahedron 2013, 69, 6627. doi: 10.1016/j.tet.2013.05.127
72. [72]
  Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 2860. doi: 10.1021/ol200855t
73. [73]
  Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. Synthesis 2012, 44, 1792. doi: 10.1055/s-0031-1289715
74. [74]
  Gilchrist, T. L.; John Harris, C.; King, F. D.; Peek, M. E. J. Chem. Soc., Perkin Trans. 1 1988, 2169.
75. [75]
  Morofuji, T.; Shimizu, A.; Yoshida, J. Chem. Eur. J. 2015, 21, 3211. doi: 10.1002/chem.v21.8
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
3. [3]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
4. [4]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
5. [5]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
6. [6]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
7. [7]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
8. [8]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
9. [9]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
10. [10]
  Yuyang Xu , Ruying Yang , Yanzhe Zhang , Yandong Liu , Keyi Li , Zehui Wei . Research Progress of Aflatoxins Removal by Modern Optical Methods. University Chemistry, 2024, 39(11): 174-181. doi: 10.12461/PKU.DXHX202402064
11. [11]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
12. [12]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
13. [13]
  Huiwei Ding , Bo Peng , Zhihao Wang , Qiaofeng Han . Advances in Metal or Nonmetal Modification of Bismuth-Based Photocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2305048-0. doi: 10.3866/PKU.WHXB202305048
14. [14]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
15. [15]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
16. [16]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
17. [17]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
18. [18]
  Mengzhen JIANG , Qian WANG , Junfeng BAI . Research progress on low-cost ligand-based metal-organic frameworks for carbon dioxide capture from industrial flue gas. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 1-13. doi: 10.11862/CJIC.20240355
19. [19]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2066)
HTML views(398)

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