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.
1. [1]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
2. [2]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
3. [3]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
4. [4]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
5. [5]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
6. [6]
  Ruolin CHENG , Yue WANG , Xiyao NIU , Huagen LIANG , Ling LIU , Shijian LU . Efficient photothermal catalytic CO₂ cycloaddition over W₁₈O₄₉/rGO composites. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1276-1284. doi: 10.11862/CJIC.20240424
7. [7]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
8. [8]
  Xudong Liu , Huili Fan , Junping Xiao , Min Yang , Yan Li . Teaching Approaches to the A_E + A_N Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041
9. [9]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
10. [10]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
11. [11]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
12. [12]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
13. [13]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
14. [14]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
15. [15]
  Yang Lei , Jieqiong Cai , Daming Sun , Caihong Tao . Exploration and Practice of Integrating Moral Education with Engineering Talent Development in the Instruction of “Principles of Chemical Engineering”. University Chemistry, 2025, 40(3): 230-236. doi: 10.12461/PKU.DXHX202406071
16. [16]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
17. [17]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-0. doi: 10.3866/PKU.WHXB202406007
18. [18]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
19. [19]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
20. [20]
  Tao Wen , Tao Zhang , Changguo Sun , Jinyu Liu . Preparation of Dess-Martin Reagent and Its Application in Oxidizing Cyclohexanol. University Chemistry, 2024, 39(5): 20-26. doi: 10.3866/PKU.DXHX202309055

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1305)
HTML views(203)

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