Citation: Wan Hongwei, Yu Jian, Yang Shoushan, Du Guangfen, He Lin. Formal[2+1] Annulation of Thiazoles and Stable Sulfur Ylide[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2549-2559. doi: 10.6023/cjoc201902003 shu

Formal[2+1] Annulation of Thiazoles and Stable Sulfur Ylide

School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832000

Corresponding author: Du Guangfen, duguangfen@shzu.edu.cn
Received Date: 8 February 2019
Revised Date: 21 April 2019
Available Online: 26 September 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21662029) and the Young Scientists Foundation of Shihezi University (Nos. RCZX201546, 2015ZRKXJQ05)the Young Scientists Foundation of Shihezi University 2015ZRKXJQ05the Young Scientists Foundation of Shihezi University RCZX201546the National Natural Science Foundation of China 21662029

Figures(5)

Thiazolones underwent formal[2+1] annulation with stable sulfur ylide to construct cyclopropane-fused spiro-thiazolone derivatives in 30%~99% yields with good diastereoselectivity.
- thiazolones,
- sulfur ylide,
- annulation,
- spiro-cyclopropane
1. [1]
  (a) Zheludkevich, M. L.; Yasakau, K. A.; Poznyak, S. K.; Ferreira, M. G. S. Corros. Sci. 2005, 47, 3368.
  (b) Jin, Z. Nat. Prod. Rep. 2006, 23, 464.
  (c) Choi, H.; Pereira, A. R.; Cao, Z.; Shuman, C. F.; Engene, N.; Byrum, T.; Matainaho, T.; Murray, T. F.; Mangoni, A.; Gerwick, W. H. J. Nat. Prod. 2010, 73, 1411.
  (d) Luzina, E. L.; Popov, A. V. Eur. J. Med. Chem. 2009, 44, 4944.
  (e) Zaharia, V.; Ignat, A.; Palibroda, N.; Ngameni, B.; Kuete, V.; Fokunang, C. N.; Moungang, M. L.; Ngadjui, B. T. Eur. J. Med. Chem. 2010, 45, 5080.
2. [2]
  (a) Siddiqui, N.; Arshad, M. F.; Ahsan, W.; Alam, M. S. Int. J. Pharm. Sci. Drug Res. 2009, 1, 136.
  (b) Ayati, A.; Emami, S.; Asadipour, A.; Shafiee, A.; Foroumadi, A. Eur. J. Med. Chem. 2015, 97, 699.
3. [3]
  (a) Thibodeaux, C. J.; Chang, W. C.; Liu, H. W. Chem. Rev. 2012, 112, 1681.
  (b) Chen, Y. K.; Pouwerb, R. H.; Richard, J. A. Chem. Soc. Rev. 2012, 41, 4631.
  (c) Reddy, C. N.; Nayak, V. L.; Mani, G. S.; Kapure, J. S.; Adiyala, P. R.; Maurya, R. A.; Kamal, A. Bioorg. Med. Chem. Lett. 2015, 25, 4580.
  (d) Talele, T. T. J. Med. Chem. 2016, 59, 8712.
  (e) Zhang, M. Z.; Chen, Q.; Yang, G. Eur. J. Med. Chem. 2015, 89, 421.
4. [4]
  (a) Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625.
  (b) Charette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327.
  (c) Barrett, A. G. M.; Kasdorf, K. J. Am. Chem. Soc. 1996, 118, 11030.
5. [5]
  (a) Li, J-L.; Yang, K.; Li, Q.; Li, Q.; Leng, H.; Shen, X.; Liu, Y.; Zhu, H. CN 960844, 2018.
  (b) Killoran, M.; Encell, L. P.; Hall, M. P.; Kirkland, T. A.; Meisenheimer, P.; Shi, C. US 1085060, 2018.
  (c) Dragovich, P.; Pei, Z.; Pillow, T.; Sadowsky, J.; Chen, J.; Wai, J. US 628464, 2017.
  (d) Henriksson, M.; Homan, E.; Johansson, L.; Vallgarda, J.; Williams, M.; Bercot, E.; Fotsch, C. H. US 1289659, 2005.
6. [6]
  (a) Maas, G. Chem. Soc. Rev. 2004, 33, 183.
  (b) Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
7. [7]
  (a) Li, A. H.; Dai, L. X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
  (b) Mcgarrigle. E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841.
  (c) Sun, X. L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937.
  (d) Zhu, C. Y.; Ding, Y.; Ye, L. W. Org. Biomol. Chem, 2015, 13, 2530.
  (e) Lu, L; Li, T.; Wang, Q.; Xiao, W. Chem. Soc. Rev. 2017, 46, 4135.
8. [8]
  Luo, J.; Wu, B.; Chen, M. W.; Jiang, G. F.; Zhou, Y. G. Org. Lett. 2014, 16, 2578. doi: 10.1021/ol500948r
9. [9]
  Yuan, Z. B.; Fang, X. X.; Li, X. Y.; Wu, J.; Yao, H. Q.; Lin, A. J. J. Org. Chem. 2015, 80, 11123. doi: 10.1021/acs.joc.5b01793
10. [10]
  (a) Zhang, X. Z.; Du, J. Y.; Deng, Y. H.; Chu, W. D.; Yan, X.; Yu, K. Y.; Fan, C. A. J. Org. Chem. 2016, 81, 2598.
  (b) Li, J.; Liu, G. L.; Zhao, X. H.; Du, J. Y.; Qu, H.; Chu, W. D.; Ding, M.; Jin, C. Y.; Wei, M. X.; Fan, C. A. Chem. Asian J. 2013, 8, 1105.
  (c) Du, J.; Zeng, C.; Han, X.; Qu, H.; Zhao, X.; An, X.; Fan. C. J. Am. Chem. Soc. 2015, 137, 4267.
  (d) Chu, W. D.; Zhang, L. F.; Bao, X.; Zhao, X. H.; Zeng, C.; Du, J. Y.; Zhang, G. B.; Wang, F. X.; Ma, X. Y.; Fan, C. A. Angew. Chem, Int. Ed. 2013, 52, 9229.
11. [11]
  Zhang, S.; Hu, X. Q.; Wang, Z. Y.; Xu, P. F. Synthesis 2015, 47, 2529. doi: 10.1055/s-0034-1380522
12. [12]
  Li, Y.; Li, Q. Z.; Huang, L.; Liang, H.; Yang, K. C.; Leng, H. J.; Liu, Y.; Shen, X. D.; Gou, X. J.; Li, J. L. Molecules 2017, 22, 328. doi: 10.3390/molecules22020328
13. [13]
  Tang, X.; Zhu, H. P.; Zhou, J.; Chen, Y.; Pan, X. L.; Guo, L.; Li, J. L.; Peng, C.; Huang, W. Org. Biomol. Chem. 2018, 16, 8169. doi: 10.1039/C8OB02034E
14. [14]
  (a) Mei, H. J.; Pan, G. H.; Zhang, X. Y.; Lin, L. L.; Liu, X. H.; Feng, X. M. Org. Lett. 2018, 20, 7794.
  (b) Wang, L.; Cao, W.; Mei, H.; Hu, L.; Feng, X. Adv. Synth. Catal. 2018, 360, 4089.
15. [15]
  (a) (k) Liang, Z.; Yi, L.; Chen, K.; Ye, S. J. Org. Chem. 2016, 81, 4841.
  (b) Lv, H.; Jia, W.; Sun, L.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 8607.
  (c) Lin, L.; Yang, Y.; Wang, M.; Lai, L.; Guo, Y.; Wang, R. Chem. Commun. 2015, 51, 8134.
  (d) Wang, C.; Gao, Z.; Zhou, L.; Yuan, C.; Sun, Z.; Xiao, Y.; Guo, H. Org. Lett. 2016, 18, 3418.
  (e) Wang, S.; Izquierdo, J.; Rodríguezescrich, C.; Pericàs, M. A. Adv. Synth. Catal. 2017, 7, 2780.
  (f) Li, S.; Chen, X. Y.; Sheng, H.; Essen, C.; Rissanen, K.; Enders, D. Synthesis 2018, 50, 1047.
  (g) Daniel, K.; Nuno, M. J. Org. Chem. 2016, 81, 4841.
  (h) Dai, Q. S.; Xiang, Z.; Yang, K. C.; Li, M. H.; Jie, Y.; Li, Q. Z.; Xin, F.; Bo, H.; Li, J. L, Adv. Synth. Catal. 2018, 360, 4435.
  (i) Cui, L.; Wang, Y. M.; Zhou, Z. H. Tetrahedron 2016, 27, 1056.
  (j) Tan, E.; Konovalov, A. I.; Fernández, G. A.; Dorel, R.; Echavarren, A. M. Org. Lett. 2016, 18, 3418.
  (k) Wu, B.; Chen, M. W.; Ye, Z. S.; Yu, C. B.; Zhou, Y. G. Adv. Synth. Catal. 2014, 356, 383.
  (l) He, Y.; Yu, A.; Meng, X. Heterocycles 2018, 96, 1108.
16. [16]
17. [17]
  Aggarwal, V. K; Grange, E. Chem.-Eur. J. 2006, 12, 568. doi: 10.1002/chem.200500693
18. [18]
  (a) Okawara, T.; Kashihara, H.; Furukawa, M. Chem. Pharm. Bull. 1985, 33, 3479.
  (b) Hofmann, B.; Barzen, S.; Rödl, C. B.; Kiehl, A.; Borig, J.; Živković, A.; Stark, H.; Schneider, G.; Steinhilber, D. J. Med. Chem. 2011, 54, 1943.
19. [19]
  CCDC 1893557 (3a) contains the supplementary crystallographic data for this paper. These data are free of charge from The Cambridge Crystallographic Centre via www.ccdc.cam.ac.uk/data_request/cif. For details, see Supporting Information.
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