Citation: Xiao Liwei, Zhang Guangxia, Jing Xuemin, Zhou Qiuxiang, Feng Ru. Recent Development of Synthesis of Functionalized Polysubstituted Oxazoles[J]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 1000-1013. doi: 10.6023/cjoc201510032 shu

Recent Development of Synthesis of Functionalized Polysubstituted Oxazoles

1.
Faculty of Chemistry and Material Science, Langfang Teachers University, Langfang 065000

Corresponding author: Xiao Liwei, xiaoliwei2000@sina.com
Received Date: 27 October 2015
Revised Date: 20 December 2015

Fund Project: Project supported by the Natural Science Foundation of Hebei Province No. B2013408014and the Educational Commission of Hebei Province No. ZD2016046

Figures(36)

Functionalized multi-substituted oxazoles including di-and tri-substituted oxazoles, play important roles in the field of pharmaceutical, catalysis and supramolecular chemistry, etc. Based on different starting materials and different methods, the recent advances in synthesis of functionalized multi-substituted oxazoles are reviewed.
- functionalized polysubstituted oxazoles,
- green chemistry,
- non-metal catalysis,
- tandem reaction
1. [1]
  Palmer, D. C.; Taylor, E. C. The Chemistry of Heterocyclic Compounds. Oxazoles: Synthesis, Reactions and Spectroscopy, Parts Wiley, Hoboken, NJ, 2004, Vol. 60.
2. [2]
  Yeh, V. S. C. Tetrahedron 2004, 60, 11995.
3. [3]
  Jin, Z. Nat. Prod. Rep. 2009, 26, 382.
4. [4]
  Hartmann-Thompson, C.; Keeley, D. L.; Pollock, K. M.; Dvornic, P. R.; Keinath, S. E.; Dantus, M.; Gunaratne, T.C.; LeCaptain, D. J. Chem. Mater. 2008, 20, 2829.
5. [5]
  Fuwa, H.; Naito, S.; Goto, T.; Sasaki, M. Angew. Chem. 2008, 120, 4815.
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
  Zheng, M.; Huang, L.; Huang, H.; Li, X.; Wu, W.; Jiang, H. Org.Lett. 2014, 16, 5906.
11. [11]
  Shaw, A. Y.; Xu , Z.; Hulme, C. Tetrahedron Lett.2012, 53, 1998.
12. [12]
  Kumar, M. P.; Liu, R.-S. J. Org. Chem.2006, 71, 4951.
13. [13]
  Milton, M. D.; Inada, Y.; Nishibayashi, Y.; Uemura, S. Chem. Commun. 2004, 2712.
14. [14]
  Pan, Y.; Zheng, F.; Lin, H.; Zhan, Z. J. Org. Chem.2009, 74, 3148.
15. [15]
  Wipf, P.; Aoyama, Y.; Benedum, T. E.; Org. Lett. 2004, 6, 3593.
16. [16]
  Ritson, D. J.; Spiteri, C.; Moses, J. E. J. Org. Chem. 2011, 76, 3519.
17. [17]
  Gao, W.-C.; Wang, R.-L.; Zhang, C. Org. Biomol. Chem. 2013, 11, 7123.
18. [18]
  Zhao, Q.; Liu, S.; Li, Y.; Wang,Q. J. Agric. Food Chem.2009, 57,2849.
19. [19]
  Dinda, M.; Samanta, S.; Eringathodiab, S.; Ghosh, P. K. RSC Adv. 2014, 4, 12252.
20. [20]
  Thalhammer, A.; Mecinovic, J.; Schofield, C. J. Tetrahedron Lett.2009, 50, 1045.
21. [21]
  Giddens, A. C.; Boshoff, H. I. M.; Franzblau, S. G.; Barry III, C. E.; Coppa, B. R. Tetrahedron Lett. 2005, 46, 7355.
22. [22]
  Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Org. Lett. 2000, 2, 1165.
23. [23]
  Chudasama, V.; Wilden, J. D.Chem. Commun. 2008, 3768.
24. [24]
  Tsai,Y.-L.; Fan,Y.-S.; Lee, C.-J.; Huang, C.-H.; Das, U.; Lin, W. Chem. Commun.2013, 49, 10266.
25. [25]
  Panda, N.; Mothkuri, R.New J. Chem.2014, 38, 5727.
26. [26]
  Zheng, Y.; Li, X.; Ren, C.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. J. Org. Chem.2012, 77, 10353.
27. [27]
  Fan, Y.-S.; Das, U.; Hsiao, M.-Y.; Liu, M.-H.; Lin, W. J. Org. Chem. 2014, 79, 11567.
28. [28]
  Martín, R.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 5521.
29. [29]
  Xu, W.; Kloeckner, U.; Nachtsheim, B. J. J. Org. Chem.2013, 78, 6065.
30. [30]
  Morwick, T.; Hrapchak, M.; DeTuri, M.; Campbell, S. Org. Lett. 2002, 4, 2665.
31. [31]
  Zhang, J.; Coqueron, P.-Y.; Vors, J.-P.; Ciufolini, M. A. Org. Lett.2010, 12, 3942
32. [32]
  Spencer, J.; Patel, H.; Amin, J.; Callear, S. K.; Coles, S. J.; Deadman, J. J.; Furman, C.; Mansouri, R.; Chavatte, P.; Millet,R. Tetrahedron Lett. 2012, 53, 165.
33. [33]
  Huang, W.; Dong, G.; Mijiti,Z.Tetrahedron2012, 68, 977.
34. [34]
  Pulici, M.; Quartieri, F.; Felder, E. R. J. Comb. Chem.2005, 7,463.
35. [35]
  Graham, T. H. Org. Lett.2010, 12, 3614.
36. [36]
  Glöckner, S.; Tran, D. N.; Ingham, R. J.; Fenner, S.; Wilson, Z. E.; Battilocchio, C.; Ley, S. V. Org. Biomol. Chem. 2015, 13, 207.
37. [37]
  Wan, C.; Zhang, J.; Wang, S.; Fan, J.; Wang, Z.Org. Lett.2010, 12,2338.
38. [38]
  Xie, J.; Jiang, H.; Cheng, Y.; Zhu, C. Chem. Commun.2012, 48, 979.
39. [39]
  Naresh, G.; Narende, T. RSC Adv. 2014, 4, 11862.
40. [40]
  Yuan, G.; Zhu, Z.; Gao, X.; Jiang, H. RSC Adv. 2014, 4, 24300.
41. [41]
  Hu, P.; Wang, Q.; Yan, Y.; Zhang, S.; Zhang, B.; Wang, Z. Org. Biomol. Chem. 2013, 11, 4304.
42. [42]
  Patil, P. C.; Luzzio, F. A.; Demuth, D. R.Tetrahedron Lett. 2015, 56, 3039.
43. [43]
44. [44]
  Liu, X.; Cheng, R.; Zhao, F.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Org. Lett.2012, 14, 5480.
45. [45]
  Kawano, Y.; Togo, H. Tetrahedron 2009, 65, 6251.
46. [46]
  Ishiwata, Y.; Togo, H. Tetrahedron 2009, 65, 10720.
47. [47]
  Saito, A.; Taniguchi, A.; Kambara, Y.; Hanzawa, Y. Org. Lett. 2013, 15, 2672.
48. [48]
  Herrera, A.; Martínez-Alvarez, R.; Ramiro, P.; Molero, D.; Almy, J. J. Org. Chem.2006, 71, 3026.
49. [49]
  Baumann, M.; Baxendale, I. R.; Ley, S. V.; Smith, C. D.; Tranmer, G. K. Org. Lett. 2006, 8, 5231.
50. [50]
  Wang, Q.; Ganem, B. Tetrahedron Lett. 2003, 44, 6829.
51. [51]
  Senadi, G. C.; Hu, W.-P.; Hsiao, J.-S.; Vandavasi, J. K.; Chen, C.-Y.; Wang, J.-J. Org. Lett. 2012, 14, 4478.
52. [52]
  Chatzopoulou, E.; Davies, P. W. Chem. Commun.2013, 49, 8617.
53. [53]
  Hashmi, A. S K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391.
54. [54]
  Wachenfeldt, H.; Rǒse, P.; Paulsen, F.; Loganathan, N.; Strand, D. Chem. Eur. J. 2013, 19, 7982.
55. [55]
  Wachenfeldt, H.; Polukeev, A. V.; Loganathan, N.; Paulsen, F.; Röse, P.; Garreau, M.; Wendt, O. F.; Strand, D. Dalton Trans.2015, 44, 5347.
56. [56]
  He, W.; Li, C.; Zhang, L. J. Am. Chem. Soc.2011, 133, 8482.
57. [57]
  Hu, Y.; Yi, R.; Wu, F.; Wan, B. J. Org. Chem.2013, 78, 7714.
58. [58]
  Zhang, L.; Zhao, X. Org. Lett. 2015, 17, 184.
59. [59]
  Zheng, J.; Zhang, M.; Huang, L.; Hu, X.; Wu, W.; Huang, H.; Jiang, H. Chem. Commun.,2014, 50, 3609.
60. [60]
  Zhao, F.; Liu, X.; Qi, R.; Zhang-Negrerie, D.; Huang, J.; Du, Y.; Zhao, K.J. Org. Chem. 2011, 76, 10338.
61. [61]
  Xie, H.; Yuan, D.; Ding, M.-W. J. Org. Chem. 2012, 77, 2954.
62. [62]
  Jiang, H.; Huang, H.; Cao, H.; Qi, C. Org. Lett. 2010, 12,5561.
63. [63]
  Shi, B.; Blake, A. J.; Lewis, W.; Campbell, I. B.; Judkins, B. D.; Moody, C. J.J. Org. Chem. 2010, 75, 152.
64. [64]
  Xu, X.; Zavalij, P. Y.; Hu, W.; Doyle, M. P. Chem. Commun.2012, 48, 11522.
65. [65]
  Murali Dhar, T. G.; Guo, J.; Shen, Z.; Pitts, W. J.; Gu, H. H.; Chen, B.-C.; Zhao, R.; Bednarz, M. S.; Iwanowicz, E. J. Org. Lett. 2002, 4, 2091.
66. [66]
  Keni, M.; Tepe, J. J. J. Org. Chem.2005, 70, 4211.
67. [67]
  Zhong, C. L.; Tang, B. Y.; Yin, P.; Chen, Y.; He, L. J. Org. Chem.2012, 77, 4271.
68. [68]
  Misra, N. C.; Ila, H. J. Org. Chem. 2010, 75, 5195.
69. [69]
  Kumar, S. V.; Saraiah, B.; Misra, N. C.; Ila, H. J. Org. Chem. 2012, 77, 10752.
70. [70]
  Hodgetts, K. J.; Kershaw,M. T.Org. Lett. 2002, 4, 2905.
71. [71]
  Miller, R. A.; Smith, R. M.; Marcune, B. J. Org. Chem.2005, 70, 9074.
72. [72]
  Tabuchi, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2014, 79, 5401.
73. [73]
  Ohnmacht, S. A.; Mamone, P.; Culshawb, A. J.; Greaney, M. F. Chem. Commun. 2008, 1241.
74. [74]
  Lee, K.; Counceller, C. M.; Stambuli, J. P. Org. Lett.2009, 11, 1457.
75. [75]
  Langille, N. F.; Dakin, L. A.; Panek, J. S. Org. Lett.2002, 4, 2485.
76. [76]
  Hoffman, T. J.; Rigby, J. H.; Arseniyadis, S.; Cossy, J. J. Org. Chem.2008, 73, 2400.
77. [77]
  Selvi, T.; Srinivasan, K. Chem. Commun.2014, 50, 10845.
78. [78]
  Zeng, T.-T.; Xuan,J.; Ding, W.; Wang, K.; Lu, L.-Q.; Xiao, W.-J. Org. Lett. 2015, 17, 4070.
1. [1]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
2. [2]
  Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
3. [3]
  Fangfang Tan , Lele Zhang , Penghua Jing , Pengju Zhao , Yang Li . 烯烃光催化氧化制备二苯甲酮——介绍一个绿色合成综合实验. University Chemistry, 2026, 41(8): 380-388. doi: 10.12461/PKU.DXHX202507049
4. [4]
  Yajun Hou , Jinxin Liu , Tao Chen , Yi Zhang , Lei Zhou . Sonogashira coupling reaction in ionic liquids: a detailed exploration of experiment 4.4D in the “101 Plan” synthetic chemistry curriculum. University Chemistry, 2026, 41(6): 136-144. doi: 10.12461/PKU.DXHX202510101
5. [5]
  Hongshen Lin , Yuxiao Hu , Wenju Chang , Jie Shen . P(III)/P(V)催化循环在Wittig反应中的应用研究进展. University Chemistry, 2026, 41(10): 118-126. doi: 10.12461/PKU.DXHX202510003
6. [6]
  Xiaoyu Wang , Yifan Li , Ruibo Liu , Li An , Dan Qu , Yichang Liu , Zaicheng Sun . Graphitic Carbon Nitride Catalyzed Photochemical Minisci Reaction: A Comprehensive Experimental Design Derived from Scientific Research. University Chemistry, 2026, 41(4): 363-371. doi: 10.12461/PKU.DXHX202502065
7. [7]
  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
8. [8]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
9. [9]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . Electrochemical CO₂ Reduction to C₂₊ Products with Ampere-Level Current on Carbon-Modified Copper Catalysts. Acta Physico-Chimica Sinica, 2025, 41(3): 100024-0. doi: 10.3866/PKU.WHXB202404012
10. [10]
  Xiaomin Kang , Chuanbao Jiao . Application of Metal-Organic Frameworks in CO₂ Catalytic Conversion: Promoting “Double Carbon” Actions for a Beautiful China. University Chemistry, 2026, 41(2): 208-217. doi: 10.12461/PKU.DXHX202503011
11. [11]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
12. [12]
  Zhiqiang Hao , Jinyue Li , Shiqi Zhang , Yujia Hou , Helue Sun . 维生素B₂促进的光催化氧化合成二苯甲酮. University Chemistry, 2026, 41(5): 350-357. doi: 10.12461/PKU.DXHX202510080
13. [13]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
14. [14]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
15. [15]
  Ronglan Zhang , Lei Hou , Dong Yang , Jie Chen , Hongshan Ke , Lin Bao , Wenjuan Shi , Jianli Li , Yan Li , Bin Cui . 无机化学与化学分析实验I课程与教材建设改革. University Chemistry, 2026, 41(8): 19-29. doi: 10.12461/PKU.DXHX202508025
16. [16]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
17. [17]
  Yifan Liu , Haonan Peng . AI-Assisted New Era in Chemistry: A Review of the Application and Development of Artificial Intelligence in Chemistry. University Chemistry, 2025, 40(7): 189-199. doi: 10.12461/PKU.DXHX202405182
18. [18]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
19. [19]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
20. [20]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(4365)
HTML views(954)

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