Citation: Ding Yuxin, Ma Yongmin, Chen Jing. Novel Three-Component Annulation for the Synthesis of 2, 4, 6-Triaryl-pyrimidines under Solvent-Free and Catalyst-Free Conditions[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4357-4363. doi: 10.6023/cjoc202005078 shu

Novel Three-Component Annulation for the Synthesis of 2, 4, 6-Triaryl-pyrimidines under Solvent-Free and Catalyst-Free Conditions

Ding Yuxin ^a,b ,
Ma Yongmin ^a,b,, ,
Chen Jing ^a,,

a.
School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, Zhejiang 310053
b.
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, Zhejiang 318000

Corresponding author: Ma Yongmin, yongmin.ma@tzc.edu.cn Chen Jing, cjmaggie@163.com
Received Date: 28 May 2020
Revised Date: 28 June 2020
Available Online: 22 July 2020
Fund Project: the Natural Science Foundation of Zhejiang Province LY19H300001the "Teacher Professional Development Project" for Domestic Visitors of Institutions of Higher Learning in 2019 FX2019020Project supported by the Natural Science Foundation of Zhejiang Province (No. LY19H300001), the Zhejiang Chinese Medicinal University Foundation (No. 2018ZG31) and the "Teacher Professional Development Project" for Domestic Visitors of Institutions of Higher Learning in 2019 (No. FX2019020)the Zhejiang Chinese Medicinal University Foundation 2018ZG31

Figures(4)

2, 4, 6-Triarylpyrimidines were synthesized via a simple, efficient, one-pot, three-component reaction from 1, 3-dikeones, benzaldehydes and ammonium acetate under solvent-free and catalyst-free conditions in good to excellent yields. This "green" methodology provides an eco-friendly protocol for the construction of the pyrimidine framework.
- catalyst-free,
- solvent-free,
- one-pot,
- three-component reaction,
- 2, 4, 6-triarylpyrimidine
1. [1]
  (a) Santos, M. F. C.; Harper, P. M.; Williams, D. E.; Mesquita, J. T.; Pinto, É. G.; da Costa-Silva, T. A.; Hajdu, E.; Ferreira, A. G.; Santos, R. A.; Murphy, P. J. J. Nat. Prod. 2015, 78, 1101.
  (b) Pettit, G. R.; Tang, Y.; Zhang, Q.; Bourne, G. T.; Hooper, J. N. A. J. Nat. Prod. 2013, 76, 420.
2. [2]
  (a) Hou, J.; Wan, S.; Wang, G.; Zhang, T.; Li, Z.; Tian, Y.; Yu, Y.; Wu, X.; Zhang, J. Eur. J. Med. Chem. 2016, 118, 276.
  (b) Agarwal, A.; Srivastava, K.; Puri, S. K.; Chauhan, P. M. S. Bioorg. Med. Chem. 2005, 13, 4645.
  (c) Parker, W. B. Chem. Rev. 2009, 109, 2880.
  (d) Shipe, W. D.; Sharik, S. S.; Barrow, J. C.; McGaughey, G. B.; Theberge, C. R.; Uslaner, J. M.; Yan, Y.; Renger, J. J.; Smith, S. M.; Coleman, P. J.; Cox, C. D. J. Med. Chem. 2015, 58, 7888.
  (e) Johar, M.; Manning, T.; Kunimoto, D. Y.; Kumar, R. Bioorg. Med. Chem. 2005, 13, 6663.
  (f) Agarwal, A.; Srivastava, K.; Puri, S. K.; Chauhan, P. M. S. Bioorg. Med. Chem. Lett. 2005, 15, 1881.
  (g) Guo, Y.; Li, J.; Ma, J.; Yu, Z.; Wang, H.; Zhu, W.; Liao, X.; Zhao, Y. Chin. Chem. Lett. 2015, 26, 755.
  (h) Chen, W.; Li, Y.; Zhou, Y.; Ma, Y.; Li, Z. Chin. Chem. Lett. 2019, 30, 2160.
  (i) Shao, K.; Zhang, X.; Zhang, X.; Xue, D.; Ma, L.; Zhang, Q.; Liu, H. Chin. J. Chem. 2014, 32, 443.
3. [3]
  (a) Undheim, K.; Benneche, T. In Comprehensive Heterocyclic Chemistry II, Vol. 6, Eds.: Katritzky, A. R.; Rees, C. W.; Scriven, E. V. F., Pergamon Press, London, 1996, p. 93.
  (b) Brown, D. J.; Evans, R. F.; Cowden, W. B. In The Pyrimidines, Vol. 52, Eds.: Taylor, E. C.; Weissberger, A., John Wiley, New York, 1994.
4. [4]
  (a) Gompper, R.; Mair, H.-J.; Polborn, K. Synthesis 1997, 696.
  (b) Bassani, D. M.; Lehn, J. A.; Baum, G.; Fenske, D. Angew. Chem., Int. Ed. 1997, 36, 1845.
  (c) Zhao, F.; Zhao, X.; Peng, B.; Gan, F.; Yao, M.; Tan, W.; Dong, J.; Zhang, Q. Chin. Chem. Lett. 2018, 29, 1692.
5. [5]
  (a) Wong, K.-T.; Hung, T. S.; Lin, Y.; Wu, C.-C.; Lee, G.-H.; Peng, S.-M.; Chou, C. H.; Su, Y. O. Org. Lett. 2002, 4, 513.
  (b) Li, L.; Fang, Y.; Chen, H.; Zhang, Y. Chin. J. Chem. 2012, 30, 1144.
6. [6]
  (a) Harriman, A.; Ziessel, R. Coord. Chem. Rev. 1998, 171, 331.
  (b) Harriman, A.; Ziessel, R. Chem. Commun. 1996, 32, 1707.
7. [7]
  (a) Dodson, R. M.; Seyler, J. K. J. Org. Chem. 1951, 16, 461.
  (b) Guo, W. Chin. Chem. Lett. 2016, 27, 47.
  (c) Chu, X. Q.; Cao, W.-B.; Xu, X.-P.; Ji, S.-J. J. Org. Chem. 2017, 82, 1145.
8. [8]
  Yuan, J.; Li, J.; Wang, B.; Sun, S.; Cheng, J. Tetrahedron Lett. 2017, 58, 4783. doi: 10.1016/j.tetlet.2017.11.020
9. [9]
  Wang, P.; Zhang, X.; Liu, Y.; Chen, B. Asian J. Org. Chem. 2019, 8, 1122. doi: 10.1002/ajoc.201900248
10. [10]
  (a) Deibl, N.; Ament, K.; Kempe, R. J. Am. Chem. Soc. 2015, 137, 12804.
  (b) Bule, M. H.; Esfandyari, R.; Tafesse, T. B.; Amini, M.; Faramarzi, M. A.; Abdollahi, M. J. Chem. Pharm. Res. 2019, 11, 27
  (c) Shi, T.; Qin, F.; Q. Zhang, Li, W. Org. Biomol. Chem. 2018, 16, 9487.
11. [11]
  Liu, D.; Guo, W.; Wu, W.; Jiang, H. J. Org. Chem. 2017, 82, 13609. doi: 10.1021/acs.joc.7b02113
12. [12]
  (a) Martínez, A. G.; Fernandez, A. H.; Alvarez, R. M.; Losada, M. C. S.; Vilchez, D. M.; Subramanian, L. R.; Hanack, M. Synthesis 1990, 881.
  (b) Fuji, M.; Obora, Y. Org. Lett. 2017, 19, 5569.
  (c) Su, L.; Sun, K.; Pan, N.; Liu, L.; Yin, S. F. Org. Lett. 2018, 20, 3399.
13. [13]
  Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125. doi: 10.1021/jo010573+
14. [14]
  Adib, M.; Mahmoodi, N.; Mahdavi, M.; Bijanzadeh, H. R. Tetrahedron Lett. 2006, 47, 9365. doi: 10.1016/j.tetlet.2006.10.090
15. [15]
  Seki, M.; Kubota, H.; Matsumoto, K.; Kinumaki, A.; Date, T.; Okamura, K. J. Org. Chem. 1993, 58, 6354. doi: 10.1021/jo00075a032
16. [16]
  Heravi, M. M.; Sadjadi, S.; Oskooie, H. A.; Shoar, R. H.; Bamoharram, F. F. Tetrahedron Lett. 2009, 50, 662. doi: 10.1016/j.tetlet.2008.11.105
17. [17]
  Ding, Y. X.; Ma, R. C.; Hider, R. C.; Ma, Y. M. Asian J. Org. Chem. 2020, 9, 242. doi: 10.1002/ajoc.201900700
18. [18]
  Itami, K.; Yamazaki, D.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 15396. doi: 10.1021/ja044923w
19. [19]
  Komatsu, R.; Nakao, K.; Sasabe, H.; Komatsu, R.; Hayasaka, Y.; Ohsawa, T.; Kido, J. J. Adv. Opt. Mater. 2017, 5, 1600675. doi: 10.1002/adom.201600675
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