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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 9: 3180 - 3187

DOI: https://doi.org/10.6023/cjoc202303031

Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

  • Xiaoke Zhang ,
  • Xiangru Zheng ,
  • Chaoyong Wang
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  • a Central Laboratory, Chongqing University Fuling Hospital, Chongqing 408000
    b The Third Affiliated Hospital of Chongqing Medical University, Chongqing 401120
    c Zunyi Medical University, Guizhou 563006
* E-mail: ;
* E-mail: ;

Received date: 2023-03-21

  Revised date: 2023-05-15

  Online published: 2023-06-07

Supported by

Guizhou Provincial Science and Technology Plan Program(QKHJC-ZK[2023]-495); Chongqing Natural Science Foundation(cstc2021jcyj-bsh0010)

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Abstract

Tetrazepine derivative exhibits good biological activities. Only a limited method has been devoted to constructing these frameworks to date. Therefore, an efficient and novel way was established for the synthesis of functionalized tetrazepine scaffolds through the cycloaddition reaction of azomethine imine with 1,2-azadiene formed in situ by α-halogeno hydrazones in the presence of KOH. This transformation shows excellent functional group tolerance and substrate scope.

Key words： α-halogeno hydrazone; azomethine imine; tetrazepine derivative; azadiene precursor

Cite this article

Xiaoke Zhang , Xiangru Zheng , Chaoyong Wang . Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor[J]. Chinese Journal of Organic Chemistry, 2023 , 43(9) : 3180 -3187 . DOI: 10.6023/cjoc202303031

References

[1]
For some selected examples: (a) Hu X.; Li, D.; Chu, C.; Li, X.; Wang, X. H.; Jia, Y.; Hua, H. M.; Xu, F. X. Int. J. Mol. Sci. 2018, 19, 3403.
[1]
(b) Xiao Y.; Gong Q.; Wang W. H.; Liu F.; Kong Q. H.; Pan F.; Zhang X. K.; Yu C. Y.; Hu S. S.; Fan F.; Li S. H.; Liu Y. Cancer Cell Int. 2020, 20, 371.
[1]
(c) Dong G. Q.; Liu Y.; Wu Y.; Tu J.; Chen S. Q.; Liu N.; Sheng C. Q. Chem. Commun. 2018, 54, 13535.
[1]
(d) Fu D. J.; Li J.; Yu B. Eur. J. Med. Chem. 2021, 214, 113254.
[1]
(e) Abdel-Halim M.; Sigler S.; Racheed N. A. S.; Hefnawy A.; Fathalla R. K.; Hammam M. A.; Maher A.; Maxuitenko Y. L.; Keeton A. B.; Hartmann R. W.; Engel M.; Piazza G. A.; Abadi A. H. J. Med. Chem. 2021, 64, 4462.
[2]
(a) Krueger B. W.; Fischer R.; Bertram H. J.; Bretschneider T.; Boehm S.; Krebs A.; Schenke T.; Santel H. J.; Lurssen K.; Schmidt R. R.; Erdelen C.; Wachendorff-Neumann U.; Stendel, W. EP0508126, 1992.
[2]
(b) Muehlebach M.; Cederbaum F.; Cornes D.; Friedmann A. A.; Glock J.; Hall G.; Indolese A. F.; Kloer D. P.; Goupil G. L.; Maetzke T.; Meier H.; Schneider R.; Stoller A.; Szczepanski H.; Wendeborna S.; Widmer H. Pest. Manage. Sci. 2011, 67, 1499.
[2]
(c) Kamata M.; Yamashita T.; Tokkyo Koho, J. K. JP 2009196966, 2009.
[2]
(d) Kamata M.; Yamashita T.; Kina A.; Tawada M.; Endo S.; Mizukami A.; Sasaki M.; Tani A.; Nakano Y.; Watanabe Y.; Furuyama N.; Funami M.; Amano N.; Fukatsu K. Bioorg. Med. Chem. Lett. 2012, 22, 4769.
[3]
(a) Kodato S. I.; Wada H.; Saito S.; Takeda M.; Nishibata Y.; Aoe K.; Date T.; Onoda Y.; Tamaki H. Chem. Pharm. Bull. 1987, 35, 80.
[3]
(b) Mashevskaya I. V.; Makhmudov R. R.; Kuslina L. V.; Mokrushin I. G.; Shurov S. N.; Maslivets A. N. Pharm. Chem. J. 2012, 45, 660.
[3]
(c) Ibrahim S. M.; Baraka M. M.; El-Sabbagh O. I.; Kothayer H. Med. Chem. Res. 2013, 22, 1488.
[4]
Almerico A. M.; Mingoia F.; Diana P.; Barraja P.; Lauria A.; Montalbano A.; Cirrincione G.; Dattolo G. J. Med. Chem. 2005, 48, 2859.
[5]
(a) Gupta C. M.; Bhaduri A. P.; Khanna N. M. J. Med. Chem. 1968, 11, 392.
[5]
(b) Ghorab M. M.; Heiba H. I.; El-gawish M. A. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 106, 85.
[5]
(c) Hamama W. S.; El-Bana G. G.; Shaaban S.; Zoorob H. H. J. Heterocycl. Chem. 2018, 55, 971.
[6]
(a) Maggio B.; Raffa D.; Raimondi M. V.; Cascioferro S.; Plescia F.; Tolomeo M.; Barbusca E.; Cannizzo G.; Mancuso S.; Daidone G. Eur. J. Med. Chem. 2008, 43, 2386.
[6]
(b) Maggio B.; Raffa D.; Raimondi M. V. ARKIVOC 2006, xv, 120.
[6]
(c) Vahedi H.; Rajabzadeh G.; Farvandi F. Chin. Chem. Lett. 2010, 21, 1419.
[6]
(d) Darehkordi A.; Khorasani F. N.; Mohammadi M.; Kazemi E. Monatsh. Chem. 2020, 151, 1835.
[7]
For selected examples, see: (a) Zhou M. B.; Song, R. J.; Wang, C. Y.; Li, J. H. Angew. Chem., Int. Ed. 2013, 52, 10805.
[7]
(b) Feng J. J.; Lin T. Y.; Wu H. H.; Zhang J. L. J. Am. Chem. Soc. 2015, 137, 3787.
[7]
(c) Liu L. L.; Chiu P. Chem. Commun. 2011, 47, 3416.
[7]
(d) Gao H. Y.; Wu X. X.; Zhang J. L. Chem. Commun. 2010, 46, 8764.
[8]
Kumari Y. B. Heterocycl. Commun. 2007, 13, 177.
[9]
Li Z. F.; Li S. K.; Kan T. J.; Wang X. Y.; Xin X.; Hou Y. L.; Gong P. Adv. Synth. Catal. 2020, 362, 2626.
[10]
(a) Huisgen R.; Fleischmann R.; Eckell A. Tetrahedron Lett. 1960, 1, 1.
[10]
(b) Breugst M.; Reissig H. U. Angew. Chem., Int. Ed. 2020, 59, 12293.
[10]
(c) Yue G. Z.; Liu B. Chin. J. Org. Chem. 2020, 40, 3132. (in Chinese)
[10]
(乐贵洲, 刘波, 有机化学, 2020, 40, 3132.)
[11]
(a) Bakthadoss M.; Agarwal V. ChemistrySelect 2018, 3, 6960.
[11]
(b) Choi A.; Castle J.; Saruengkhanphasit R.; Coldham I. Synthesis 2020, 1273.
[11]
(c) Sandmeier T.; Sievertsen N.; Carreira E. M. Helv. Chim. Acta 2020, 103, e2000058.
[12]
(a) Li Z.; Yu H.; Liu Y.; Zhou L.; Sun Z.; Guo H. Adv. Synth. Catal. 2016, 358, 1880.
[12]
(b) Zhou L.; Yuan C.; Zhang C.; Zhang L.; Gao Z.; Wang C.; Liu H.; Wu Y.; Guo H. Adv. Synth. Catal. 2017, 359, 2316.
[12]
(c) Zhu C. Z.; Feng J. J.; Zhang J. Chem. Commun. 2017, 53, 4688.
[12]
(d) Yu L.; Zhong Y.; Yu J.; Gan L.; Cai Z.; Wang R.; Jiang X. Chem. Commun. 2018, 54, 2353.
[12]
(e) Cheng X.; Cao X.; Xuan J.; Xiao W. J. Org. Lett. 2018, 20, 52.
[13]
(a) Wei L.; Wang Z. F.; Yao L.; Qiu G. F.; Tao H. Y.; Li H.; Wang C. J. Adv. Synth. Catal. 2016, 358, 3955.
[13]
(b) Wang Y. F.; Zhu L. P.; Wang M. R.; Xiong J.; Chen N. N.; Feng X.; Xu Z. Q.; Jiang X. X. Org. Lett. 2018, 20, 6506.
[14]
(a) Li Z.; Feng Y. L.; Hou Z. F.; Zhang L.; Yang W. J.; Wu Y.; Xiao Y. M.; Guo H. C. RSC Adv. 2015, 5, 34481.
[14]
(b) Mei G. J.; Zhu Z. Q.; Zhao J. J.; Bian C. Y.; Chen J.; Chen R. W.; Shi F. Chem. Commun. 2017, 53, 2768.
[14]
(c) Li C.; Wang C. S.; Li T. Z.; Mei G. J.; Shi F. Org. Lett. 2019, 21, 598.
[14]
(d) Yuan C. H.; Zhou L. J.; Xia M. R.; Sun Z. H.; Wang D. Q.; Guo H. C. Org. Lett. 2016, 18, 5644.
[14]
(e) Na R.; Jing C.; Xu Q.; Jiang H.; Wu X.; Shi J. J. Am. Chem. Soc. 2011, 133, 13341.
[14]
(f) Wang M.; Huang Z. J.; Xu J. F.; Chi Y. R. J. Am. Chem. Soc. 2014, 136, 1214.
[14]
(g) Na R.; Jing C. F.; Xu Q. H.; Jiang H.; Wu X.; Shi J. Y.; Zhong J. C.; Wang M.; Benitez D.; Tkatchouk E.; Goddard W. A.; Guo H. C.; Kwon O. J. Am. Chem. Soc. 2011, 133, 13337.
[14]
(h) Hu X. Q.; Chen J. R.; Gao S.; Feng B.; Lu L. Q.; Xiao W. J. Chem. Commun. 2013, 49, 7905.
[14]
(i) Yang W. J.; Yuan C. H.; Liu Y.; Mao B. M.; Sun Z. H.; Guo H. C. J. Org. Chem. 2016, 81, 7597.
[15]
(a) Jin Q.; Zhang J.; Jiang C.; Zhang D.; Gao M.; Hu S. J. Org. Chem. 2018, 83, 8410.
[15]
(b) Hu X. Q.; Chen J. R.; Gao S.; Feng B.; Lu L. Q.; Xiao W. J. Chem. Commun. 2013, 49, 7906.
[15]
(c) Zhi Y.; Zhao K.; Shu T.; Enders D. Synthesis 2016, 48, 240.
[15]
(d) Chen L.; Yang G. M.; Wang J.; Jia Q. F.; Wei J.; Du Z. Y. RSC Adv. 2015, 5, 76697.
[16]
For selected examples, see: (a) Zhang X. K.; Pan, Y.; Wang, H. B.; Liang, C.; Ma, X. F.; Jiao, W.; Shao, H. W. Adv. Synth. Catal. 2021, 363, 459.
[16]
(b) Chen J. R.; Dong W. R.; Candy M.; Pan F. F.; Jo?rres M.; Bolm C. J. Am. Chem. Soc. 2012, 134, 6924.
[16]
(c) Huang R.; Chang X.; Li J.; Wang C. J. J. Am. Chem. Soc. 2016, 138, 3998.
[16]
(d) Quan B. X.; Zhuo J. R.; Zhao J. Q.; Zhang M. L.; Zhou M. Q.; Zhang X. M.; Yuan W. C. Org. Biomol. Chem. 2020, 18, 1886.
[16]
(f) Chen B.; Chu W. D.; Liu Q. Z. RSC Adv. 2019, 9, 1487.
[16]
(g) Huang R.; Chang X.; Li J.; Wang C. J. J. Am. Chem. Soc. 2016, 138, 3998.
[16]
(h) Yin W. H.; Fang L.; Wang Z. Y.; Gao F.; Li Z. F.; Wang Z. Y. Org. Lett. 2020, 21, 7361.
[16]
(i) Cao W. B.; Xu X. P.; Ji S. J. Org. Biomol. Chem. 2017, 15, 1651.
[16]
(j) Zhong X. G.; Lv J.; Luo S. Org. Lett. 2015, 17, 1561.
[16]
(k) Deng Y. M.; Pei C.; Arman H.; Dong K. Y.; Xu X. F.; Doyle M. P. Org. Lett. 2016, 18, 5884.
[17]
Zhao H. W.; Pang H. L.; Tian T.; Li B.; Chen X. Q.; Song X. Q.; Meng W.; Yang Z.; Liu Y. Y.; Zhao Y. D. Adv. Synth. Catal. 2016, 358, 1826.
[18]
Cheng B.; Li Y. T.; Wang T. M.; Zhang X. P.; Li H.; Li Y.; Zhai H. B. Chem. Commun. 2019, 55, 14606.
[19]
Zhang X. K.; Wang H. B.; Li Z. W.; Shu Y.; Gan S. Zhang X. F.; Shao H. W.; Wang C. Y. ACS Omega 2022, 7, 40963.
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