Citation: Runzhi Sun, Xiuqing Song, Shijie Wang, Xiaokun Zhang, Hong Yan, Yeming Wang. Construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes by photocycloaddition reaction of 1,4-dihydropyridines: Experimental and theoretical investigation[J]. Chinese Chemical Letters, ;2023, 34(12): 108183. doi: 10.1016/j.cclet.2023.108183 shu

Construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes by photocycloaddition reaction of 1,4-dihydropyridines: Experimental and theoretical investigation

Runzhi Sun ^a ,
Xiuqing Song ^b ,
Shijie Wang ^a ,
Xiaokun Zhang ^a ,
Hong Yan ^{a, *,} ,
Yeming Wang ^{c, *,}

a.
Faculty of Environment and Life, Beijing University of Technology, Beijing 100124, China
b.
Large-scale Instruments and Equipments Sharing Platform, Beijing University of Technology, Beijing 100124, China
c.
Beijing Tide Pharmaceutical Co., Ltd., Beijing 100176, China

hongyan@bjut.edu.cn

yemingwang@126.com

Received Date: 14 November 2022
Revised Date: 11 January 2023
Accepted Date: 29 January 2023
Available Online: 3 February 2023

Figures(8)

A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes (P₁) and 3,9-diazatetracyclododecanes (P₂) is reported for the first time. The types of reaction product clearly differ with solvent, regardless of the irradiation wavelength. The difference in P₁ and P₂ lies in the second step of the intramolecular [2 + 2] photocyclization. In order to further investigate this phenomenon and gain a deeper understanding of the photochemical behavior of 1,4-dihydropyridines, DFT and TDDFT theoretical calculations are performed. The results provide a good explanation for the formation of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes.
- 1,4-Dihydropyridine,
- Photocycloaddition,
- Theoretical investigation,
- 3,9-Diazatetracyclododecanes
1. [1]
  L.R. Domingo, S.R. Emamian, Tetrahedron 70 (2014) 1267–1273. doi: 10.1016/j.tet.2013.12.059
2. [2]
  S. Poplata, A. Tröster, Y. Zou, T. Bach, Chem. Rev. 116 (2016) 9748–9815. doi: 10.1021/acs.chemrev.5b00723
3. [3]
  V.M. Dembitsky, J. Nat. Med. 62 (2008) 1–33.
4. [4]
  S. Piao, Y. Song, W. Jiao, et al., Org. Lett. 15 (2013) 3526–3529. doi: 10.1021/ol400933x
5. [5]
  R. Medishetty, A. Husain, Z. Bai, et al., Angew. Chem. Int. Ed. 126 (2014) 6017–6021. doi: 10.1002/ange.201402040
6. [6]
  A.E. Hurtley, Z. Lu, T.P. Yoon, Angew. Chem. Int. Ed. 126 (2014) 9137–9140. doi: 10.1002/ange.201405359
7. [7]
  C. García-Morales, B. Ranieri, I. Escofet, et al., J. Am. Chem. Soc. 139 (2017) 13628–13631. doi: 10.1021/jacs.7b07651
8. [8]
  M.A. Ischay, Z. Lu, T.P. Yoon, J. Am. Chem. Soc. 132 (2010) 8572–8574. doi: 10.1021/ja103934y
9. [9]
  D. Yang, Q. Yan, E. Zhu, J. Lv, W.M. He, Chin. Chem. Lett. 33 (2022) 1798–1816. doi: 10.1016/j.cclet.2021.09.068
10. [10]
  S. He, X. Chen, F. Zeng, et al., Chin. Chem. Lett. 31 (2020) 1863–1867. doi: 10.1016/j.cclet.2019.12.031
11. [11]
  W. He, L. Gao, X. Chen, et al., Chin. Chem. Lett. 31 (2020) 1895–1898. doi: 10.1016/j.cclet.2020.02.011
12. [12]
  Z. Gan, G. Li, X. Yang, et al., Sci. China Chem. 63 (2020) 1652–1658. doi: 10.1007/s11426-020-9811-6
13. [13]
  A. Sergeiko, V.V. Poroikov, L.O. Hanus, V.M. Dembitsky, Open. Med. Chem. J. 2 (2008) 26–37. doi: 10.2174/1874104500802010026
14. [14]
  Y. Fan, X. Gao, J. Yue, Sci. China Chem. 59 (2016) 1126–1141. doi: 10.1007/s11426-016-0233-1
15. [15]
  B. Zhang, J. Chen, Chin. J. Org. Chem. 42 (2022) 3429–3430. doi: 10.6023/cjoc202200058
16. [16]
  W. Zhou, Y. Jiang, L. Chen, K. Liu, D. Yu, Chin. J. Org. Chem. 40 (2020) 3697–3713. doi: 10.6023/cjoc202004045
17. [17]
  J.M. Anderson, N.D. Measom, J.A. Murphy, D.L. Poole, Angew. Chem. Int. Ed. 60 (2021) 24754–24769. doi: 10.1002/anie.202106352
18. [18]
  J. Bertram, R. Kürsten, J. Prakt. Chem. 51 (1895) 316–325. doi: 10.1002/prac.18950510123
19. [19]
  C.N. Riiber, Ber. Dtsch. Chem. Ges. 35 (1902) 2908–2909. doi: 10.1002/cber.19020350373
20. [20]
  G. Ciamician, P. Silber, Ber. Dtsch. Chem. Ges. 35 (1902) 1992–2000. doi: 10.1002/cber.190203502148
21. [21]
  G. Ciamician, P. Silber, Ber. Dtsch. Chem. Ges. 41 (1908) 1071–1080. doi: 10.1002/cber.190804101211
22. [22]
  G. Büchi, I. Goldman, J. Am. Chem. Soc. 79 (1957) 4741–4748. doi: 10.1021/ja01574a042
23. [23]
  S. Goldmann, J. Stoltefuss, Angew. Chem. Int. Ed. 30 (1991) 1559–1578. doi: 10.1002/anie.199115591
24. [24]
  D.J. Triggle, D.A. Langs, R.A. Janis, Med. Res. Rev. 9 (1989) 123–180. doi: 10.1002/med.2610090203
25. [25]
  F. Bossert, W. Vater, Med. Res. Rev. 9 (1989) 291–324. doi: 10.1002/med.2610090304
26. [26]
  Q. Fan, H. Tan, P. Li, H. Yan, New J. Chem. 42 (2018) 16795–16805. doi: 10.1039/C8NJ02192A
27. [27]
  M.S. Saddala, R. Kandimalla, J.A. Pradeepkiran, S.S. Bhashyam, U.R. Asupatri, Sci. Rep. 7 (2017) 45211. doi: 10.1038/srep45211
28. [28]
  I. Drapak, L. Perekhoda, T. Tsapko, N. Berezniakova, Y. Tsapko, J. Heterocycl. Chem. 54 (2017) 2117–2128. doi: 10.1002/jhet.2837
29. [29]
  M. Zhang, H. Lan, N. Li, et al., J. Org. Chem. 85 (2020) 8279–8286. doi: 10.1021/acs.joc.0c00963
30. [30]
  C. Coburger, J. Wollmann, M. Krug, et al., Bioorgan. Med. Chem. 18 (2010) 4983–4990. doi: 10.1016/j.bmc.2010.06.004
31. [31]
  A. Hilgeroth, M. Wiese, A. Billich, J. Med. Chem. 42 (1999) 4729–4732. doi: 10.1021/jm991115k
32. [32]
  Y. Liu, H. Tan, H. Yan, X. Song, Chem. Biol. Drug. Des. 82 (2013) 567–578. doi: 10.1111/cbdd.12185
33. [33]
  U. Eisner, J.R. Williams, B.W. Matthews, H. Ziffer, Tetrahedron 26 (1970) 899–909. doi: 10.1016/S0040-4020(01)97888-3
34. [34]
  A. Hilgeroth, H. Lilie, Eur. J. Med. Chem. 38 (2003) 495–499. doi: 10.1016/S0223-5234(03)00060-6
35. [35]
  M. Richter, J. Molnár, A. Hilgeroth, J. Med. Chem. 49 (2006) 2838–2840. doi: 10.1021/jm058046w
36. [36]
  H. Tan, Z. Zhao, Z. Ma, H. Yan, Tetrahedron 74 (2018) 529–534. doi: 10.1016/j.tet.2017.10.019
37. [37]
  A. Hilgeroth, U. Baumeister, F.W. Heinemann, Eur. J. Med. Chem. 2000 (2000) 245–249. doi: 10.1002/(SICI)1099-0690(200001)2000:2<245::AID-EJOC245>3.0.CO;2-2
38. [38]
  A. Hilgeroth, J. Molnár, E. De Clercq, Angew. Chem. Int. Ed. 41 (2002) 3623–3625. doi: 10.1002/1521-3773(20021004)41:19<3623::AID-ANIE3623>3.0.CO;2-V
39. [39]
  A. Hilgeroth, A. Billich, Arch. Pharm. 332 (1999) 380–384. doi: 10.1002/(SICI)1521-4184(199911)332:11<380::AID-ARDP380>3.0.CO;2-T
40. [40]
  L. Mao, N. Tian, C. Wei, H. Wang, H. Yan, Russ. J. Gen. Chem. 92 (2022) 446–456. doi: 10.1134/S1070363222030124
41. [41]
  P. Chen, H. Wang, M. Li, et al., Dis. Markers. 2020 (2020) 5068067.
42. [42]
  Q. Fan, L. Zhu, H. Ren, H. Lin, G. Wu, Chem. Phys. Lett. 771 (2021) 2207–2213.
43. [43]
  H. Xin, X. Zhu, H. Yan, X. Song, Tetrahedron Lett. 54 (2013) 3325–3328. doi: 10.1016/j.tetlet.2013.04.016
44. [44]
  Q. Song, H. Wang, H. Yan, C. Ni, R. Zhong, J. Mol. Struct. 1006 (2011) 489–493. doi: 10.1016/j.molstruc.2011.09.056
45. [45]
  G.M.J. Schmidt, Pure. Appl. Chem. 27 (1971) 647–678. doi: 10.1351/pac197127040647
46. [46]
  E. García-Expósito, M.J. Bearpark, R.M. Ortuño, M.A. Robb, V. Branchadell, J. Org. Chem. 67 (2002) 6070–6077. doi: 10.1021/jo026047f
47. [47]
  P. Jaque, A. Toro-Labbé, P. Geerlings, F.D. Proft, J. Phys. Chem. A 113 (2009) 332–344. doi: 10.1021/jp807754f
48. [48]
  S. Wilsey, L. González, M.A. Robb, K.N. Houk, J. Am. Chem. Soc. 122 (2000) 5866–5876. doi: 10.1021/ja0006595
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