Citation: Zhang Zhiyong, Wang Qi, Zhang Hao, Chen Yongming, Wang Xin, Ge Zemei, Li Runtao. [3+3] Cycloaddition Reactions of Aza-oxyallyl Cations with Oximes: Synthesis of 2-N-Unsubstituted 1, 2, 4-Oxadiazinan-5-ones[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1970-1975. doi: 10.6023/cjoc201901030 shu

[3+3] Cycloaddition Reactions of Aza-oxyallyl Cations with Oximes: Synthesis of 2-N-Unsubstituted 1, 2, 4-Oxadiazinan-5-ones

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191

Corresponding author: Li Runtao, lirt@bjmu.edu.cn
Received Date: 20 January 2019
Revised Date: 28 February 2019
Available Online: 2 July 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 81673287)the National Natural Science Foundation of China 81673287

Figures(4)

The first[3+3] cycloaddition reaction of in situ-generated aza-oxyallyl cations with oximes was developed. This approach provides a simple and efficient method for the synthesis of 2-N-unsubstituted 1, 2, 4-oxadiazin-5-one derivatives with many merits, such as easy available regents, mild reaction conditions and high yield.
- 1, 2, 4-oxadiazinan-5-one,
- α-halohydroxamate,
- azaoxyallyl cations,
- oxime,
- [3+3]-cycloaddition
1. [1]
  (a) Akhtar, J.; Khan, A. A.; Ali, Z.; Haider, R.; Shahar Yar, M. Eur. J. Med. Chem. 2017, 125, 143.
  (b) Kvasnica, M.; Urban, M.; Dickinson, N. J.; Sarek, J. Nat. Prod. Rep. 2015, 32, 1303.
2. [2]
  Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b
3. [3]
  (a) Khan, I.; Ibrar, A.; Ahmed, W.; Saeed, A. Eur. J. Med. Chem. 2015, 90, 124.
  (b) Vo, C. V.; Bode, J. W. J. Org. Chem. 2014, 79, 2809.
  (c) Qiu, G.; Wu, J. Chem. Rec. 2016, 16, 19.
  (d) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505.
4. [4]
  Ueda, H.; Kurita, J. I.; Neyama, H.; Hirao, Y.; Kouji, H.; Mishina, T.; Kasai, M.; Nakano, H.; Yoshimori, A.; Nishimura, Y. Bioorg. Med. Chem. Lett. 2017, 27, 4705. doi: 10.1016/j.bmcl.2017.09.006
5. [5]
  Weller, H. N.; Miller, A. V.; Dickinson, K. E. J.; Hedberg, S. A.; Delaney, C. L.; Serafino, R. P.; Moreland, M. Heterocycles 1993, 36, 1027 doi: 10.3987/COM-92-6263
6. [6]
  (a) Xuan, J.; Cao, X.; Cheng, X. Chem. Commun. 2018, 54, 5154.
  (b) Ji, D.; Sun, J. Org. Lett. 2018, 20, 2745.
  (c) Baumann, M.; Baxendale, I. R. Beilstein J. Org. Chem. 2013, 9, 2265.
  (d) Jeffrey, C. S.; Barnes, K. L.; Eickhoff, J. A.; Carson, C. R. J. Am. Chem. Soc. 2011, 133, 7688.
  (e) Acharya, A.; Anumandla, D.; Jeffrey, C. S. J. Am. Chem. Soc. 2015, 137, 14858.
  (f) DiPoto, M. C.; Hughes, R. P.; Wu, J. J. Am. Chem. Soc. 2015, 137, 14861.
  (g) Ji, W.; Yao, L.; Liao, X. Org. Lett. 2016, 18, 628.
7. [7]
  An, Y.; Xia, H.; Wu, J. Chem. Commun. 2016, 52, 10415. doi: 10.1039/C6CC03650C
8. [8]
  Xuan, J.; Cheng, X.; Cao, X. ChemistrySelect 2017, 2, 4364. doi: 10.1002/slct.201700826
9. [9]
  Zhao, H. W.; Zhao, Y. D.; Liu, Y. Y.; Zhao, L. J.; Feng, N. N.; Pang, H. L.; Chen, X. Q.; Song, X. Q.; Du, J. RSC Adv. 2017, 7, 12916. doi: 10.1039/C6RA27440D
10. [10]
  Chen, R.; Sun, S.; Wang, G.; Guo, H. Tetrahedron Lett. 2018, 59, 1916. doi: 10.1016/j.tetlet.2018.03.085
11. [11]
  Lin, W.; Zhan, G.; Shi, M.; Du, W.; Chen, Y. Chin. J. Chem. 2017, 35, 857. doi: 10.1002/cjoc.201600864
12. [12]
  (a) Mirjafary, Z.; Abdoli, M.; Saeidian, H.; Kakanejadifard, A.; Farniad, S. M. F. RSC Adv. 2016, 6, 17740.
  (b) Khutorianskyi, A.; Chalyk, B.; Borysko, P.; Kondratiuk, A.; Mykhailiuk, P. K. Eur. J. Org. Chem. 2017, 27, 3935.
  (c) Subramanian, P.; Kaliappan, K. P. Chem.-Asian J. 2018, 13, 2031.
  (d) Slagbrand, T.; Kervefors, G.; Tinnis, F.; Adolfsson, H. Adv. Synth. Catal. 2017, 359, 1990.
13. [13]
  Wang, G.; Chen, R.; Zhao, S.; Yang, L.; Guo, H.; Sun, S.; Wang, J.; Domena, J.; Xing, Y. Tetrahedron Lett. 2018, 59, 2018. doi: 10.1016/j.tetlet.2018.04.025
14. [14]
  (a) Sousa, C. A. D.; Vale, M. L. C.; Rodríguez-Borges, J. E.; Garcia-Mera, X.; Rodríguez-Otero, J. Tetrahedron Lett. 2008, 49, 5777.
  (b) Sousa, C. A. D.; Vale, M. L. C.; Garcia-Mera, X.; Rodríguez- Borges, J. E. Tetrahedron 2012, 68, 1682.
15. [15]
  Jia, Q.; Li, D.; Lang, M.; Zhang, K.; Wang, J. Adv. Synth. Catal. 2017, 359, 3837. doi: 10.1002/adsc.201700415
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