Citation: Suo Yongbo, Xie Mingsheng, Chen Yangguang, Zhang Yiming, Guo Zhen, Li Jianping, Qu Guirong, Guo Haiming. Synthesis of 1, 2, 3, 4-Tetrazine Derivatives via [4+2] Cycloaddition of α-Halo-N-acylhydrazones with Diazodicarboxylates[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 540-546. doi: 10.6023/cjoc201511001 shu

Synthesis of 1, 2, 3, 4-Tetrazine Derivatives via [4+2] Cycloaddition of α-Halo-N-acylhydrazones with Diazodicarboxylates

1.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007

Corresponding author: Guo Haiming, guohm518@hotmail.com
Received Date: 1 November 2015
Revised Date: 24 November 2015

Fund Project: the Creative Experimental Project of National Undergraduate Students 201410476027the Creative Experimental Project of National Undergraduate Students 201310476035the National Natural Science Foundation of China 21372064the National Natural Science Foundation of China 21402041the Research Fund for the Doctoral Program of Higher Education 20124104110006

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1, 2, 3, 4-Tetrazine derivative is a kind of nitrogen-rich compounds, which exhibits higher energetic density and potential application on the field of energy materials. In this paper, through the [4+2] cycloaddition of α-halo-N-acylhydrazones to diazodicarboxylates, various 1, 2, 3, 4-tetrazine derivatives could be afforded in good to excellent yields in mild reaction conditions. The 1, 2-diaza-1, 3-dienes were generated in situ with the help of base, subsequently, in the absence of catalyst, the [4+2] cycloaddition proceeded well. Besides, this reaction can be performed on the gram scale and has good substrate scope.
- 1, 2, 3, 4-tetrazine,
- [4+2] cycloaddition,
- diazodicarboxylates,
- α-halo-N-acylhydrazones
1. [1]
  Yang, S.; Xu, S.; Huang, H.; Zhang, W.; Zhang, X. Prog. Chem. 2008, 20, 526.
2. [2]
  Tan, B.; Huang, M.; Huang, H.; Long, X.; Li, J.; Nie, F.; Huang, J. Propellants, Explos., Pyrotech. 2013, 38, 372. doi: 10.1002/prep.201200206
3. [3]
  Frumkin, A. E.; Churakov, A. M.; Strelenko, Y. A.; Kachala, V. V.; Tartakovsky, V. A. Org. Lett. 1999, 5, 721.
  (b) Klenov, M. S.; Zelenov, V. P.; Churakov, A. M.; Strelenko, Y. A.; Tartakovsky, V. A. Russ. Chem. Bull., Int. Ed. 2011, 60, 2040.
  (c) Voronin, A. A.; Zelenov, V. P.; Churakov, A. M.; Strelenko, Y. A.; Fedyanin, I. V.; Tartakovsky, V. A. Tetrahedron 2014, 70, 3018.
  (d) Voronin, A. A.; Zelenov, V. P.; Churakov, A. M.; Strelenko, Y. A.; Tartakovsky, V. A. Russ. Chem. Bull., Int. Ed. 2014, 63, 475.
4. [4]
  Sommer, S.; Schubert, U. Angew. Chem. 1979, 91, 757. doi: 10.1002/(ISSN)1521-3757
5. [5]
  Avalos, M.; Babiano, R.; Cintas, P.; Clemente, F. R.; Gordillo, R.; Hursthouse, M. B.; Jiménez, J. L.; Light, M. E.; Palacios, J. C. J. Org. Chem. 2002, 67, 2378. doi: 10.1021/jo0163391
6. [6]
  Attanasi, O. A.; Crescentini, L. D.; Favi, G.; Filippone, P.; Mantellini, F.; Perulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2009, 3109.
7. [7]
  Chen, J.-R.; Dong, W.-R.; Candy, M.; Pan, F.-F.; Jörres, M.; Bolm, C. J. Am. Chem. Soc. 2012, 134, 6924.
  (b) Attanasi, O. A.; Crescentini, L. D.; Favi, G.; Mantellini, F.; Mantenuto, S.; Nicolini, S. J. Org. Chem. 2014, 79, 8331.
8. [8]
  Guo, C.; Sahoo, B.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17402.
  (b) Hu, X.-Q.; Chen, J.-R.; Gao, S. Feng, B.; Lu, L.-Q.; Xiao, W.-J. Chem. Commun. 2013, 49, 7905.
9. [9]
  Gao, S.; Chen, J.-R.; Hu, X.-Q.; Cheng, H.-G.; Lu, L.-Q.; Xiao, W.-J. Adv. Synth. Catal. 2013, 355, 3539. doi: 10.1002/adsc.201300723
10. [10]
  Tong, M.-C.; Chen, X.; Li, J.; Huang, R.; Tao, H.; Wang, C.-J. Angew. Chem., Int. Ed. 2014, 53, 4680.
  (b) Li, J.; Huang, R.; Xing, Y.-K.; Qiu, G.; Tao, H.-Y.; Wang, C.-J. J. Am. Chem. Soc. 2015, 137, 10124.
  (c) Wei, L.; Wang, C.-J. Chem. Commun. 2015, 51, 15374.
11. [11]
  Attanasi, O. A.; Favi, G.; Mantellini, F.; Mantenuto, S.; Moscatelli, G.; Nicolini, S. Synlett 2014, 26, 193. doi: 10.1055/s-00000083
12. [12]
  Zhong, X.; Lv, J.; Luo, S. Org. Lett. 2015, 17, 1561. doi: 10.1021/acs.orglett.5b00445
13. [13]
  Sommer, S. Angew. Chem. 1979, 91, 756. doi: 10.1002/(ISSN)1521-3757
14. [14]
  Sommer, S. Chem. Lett. 1977, 583.
  (b) South, M. S.; Jakuboski, T. L.; Westmeyer, M. D.; Dukesherer, D. R. J. Org. Chem. 1996, 61, 8921.
  (c) Al-Awadi, N. A.; Ibrahim, Y. A.; John, E.; Parveen, A. Tetrahedron 2011, 67, 1298.
  (d) Attanasi, O. A.; Favi, G.; Geronikaki, A.; Mantellini, F.; Moscatelli, G.; Paparisva, A. Org. Lett. 2013, 15, 2624.
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