Citation: Hui Zheng, Ying Han, Jing Sun, Chao-Guo Yan. Convenient synthesis of hexasubstituted benzene derivatives via DABCO promoted domino reaction of arylidene malononitrile and dialkyl but-2-ynedioate[J]. Chinese Chemical Letters, ;2021, 32(5): 1683-1686. doi: 10.1016/j.cclet.2020.12.024 shu

Convenient synthesis of hexasubstituted benzene derivatives via DABCO promoted domino reaction of arylidene malononitrile and dialkyl but-2-ynedioate

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China

hanying@yzu.edu.cn

cgyan@yzu.edu.cn

Received Date: 30 October 2020
Revised Date: 16 December 2020
Accepted Date: 17 December 2020
Available Online: 19 December 2020

Figures(4)

A convenient synthetic protocol for the hexasubstituted benzene derivatives was successfully developed by DABCO promoted domino reaction of arylidene malononitrile with two molecules of dialkyl but-2-ynedioates. The domino reaction resulted in tetraalkyl 6-cyano-[1, 1'-biphenyl]-2, 3, 4, 5-tetracarboxylates in good to high yields. This formal [2 + 2 + 2] cycloaddition was believed to proceed with sequential nucleophilic addition, Michael addition, annulation and aromatization processes.
- Hexasubstituted benzene,
- Electron-deficient alkyne,
- Malononitrile,
- Annulation,
- [2 + 2 + 2] cycloaddition
1. [1]
  V. Nair, C. Rajesh, A.U. Vinod, et al., Acc. Chem. Res. 36(2003) 899-907. doi: 10.1021/ar020258p
2. [2]
  V. Nair, R.S. Menon, A. Sreekanth, et al., Acc. Chem. Res. 39(2006) 520-530. doi: 10.1021/ar0502026
3. [3]
  N. Kielland, L.R. Avilla, Top. Heterocycl. Chem. 25(2010) 127-168.
4. [4]
  A. Shaabani, A. Maleki, A.H. Rezayan, et al., Mol. Divers. 15(2011) 41-68. doi: 10.1007/s11030-010-9258-1
5. [5]
  V. Nair, A. Deepthi, D. Ashok, et al., Tetrahedron 70(2014) 3085-3105. doi: 10.1016/j.tet.2014.03.014
6. [6]
  J.W. Sun, H.Y. Hu, F.Y. Wang, et al., RSC Adv. 4(2014) 36498-36501. doi: 10.1039/C4RA06048B
7. [7]
  S. Arab-Salmanabadi, M. Dorvar, B. Notash, Tetrahedron 71(2015) 1292-1296. doi: 10.1016/j.tet.2014.12.076
8. [8]
  Y.L. Xing, M. Zhang, S. Ciccarelli, et al., Eur. J. Org. Chem. 4(2017) 781-785.
9. [9]
  S.S. Ghafouri, M.A. Afshari, N. Saeedi, et al., Asian J. Chem. 25(2013) 4111-4112. doi: 10.14233/ajchem.2013.13772
10. [10]
  J.W. Sun, F.Y. Wang, H.Y. Hu, et al., J. Org. Chem. 79(2014) 3992-3998. doi: 10.1021/jo500456d
11. [11]
  H.I. De Silva, W.P. Henry Jr., C.U. Pittman, Synthesis 44(2012) 3337-3352. doi: 10.1055/s-0032-1316790
12. [12]
  S. Arab-Salmanabadi, M. Dorvar, B. Notash, Tetrahedron 71(2015) 1292-1296. doi: 10.1016/j.tet.2014.12.076
13. [13]
  H.B. Yang, X.Y. Guan, Y. Wei, et al., Eur. J. Org. Chem. 14(2012) 2792-2800. doi: 10.1002/ejoc.201200185
14. [14]
  G.W. Wang, J.X. Li, Org. Biomol. Chem. 4(2006) 4063-4064. doi: 10.1039/b612641c
15. [15]
  J. Sun, Y. Sun, H. Gong, et al., Org. Lett. 14(2012) 5172-5175. doi: 10.1021/ol302530m
16. [16]
  J. Sun, H. Gong, Y. Sun, et al., Mol. Divers. 17(2013) 627-639. doi: 10.1007/s11030-013-9459-5
17. [17]
  J. Sun, H. Gong, C.G. Yan, Tetrahedron 69(2013) 10235-10244. doi: 10.1016/j.tet.2013.10.044
18. [18]
  J. Sun, D. Zhu, H. Gong, et al., Tetrahedron 69(2013) 10565-10572. doi: 10.1016/j.tet.2013.10.040
19. [19]
  P. Wu, H. Gao, J. Sun, et al., Chin. Chem. Lett. 28(2017) 329-332. doi: 10.1016/j.cclet.2016.07.016
20. [20]
  Y. Han, H. Zheng, Y.Y. Zhang, et al., Chin. Chem. Lett. 31(2020) 1337-1341. doi: 10.1016/j.cclet.2019.10.042
21. [21]
  Z. Cao, Q. Zhu, Y.W. Lin, et al., Chin. Chem. Lett. 30(2019) 2132-2138. doi: 10.1016/j.cclet.2019.09.041
22. [22]
  L.H. Lu, Z. Wang, W. Xia, et al., Chin. Chem. Lett. 30(2019) 1237-1240. doi: 10.1016/j.cclet.2019.04.033
23. [23]
  Y.C. He, C. Pi, Y.J. Wu, et al., Chin. Chem. Lett. 31(2020) 396-400. doi: 10.1016/j.cclet.2019.09.025
24. [24]
  Q.W. Gui, F. Teng, S.N. Ying, et al., Chin. Chem. Lett. 31(2020) 3241-3244. doi: 10.1016/j.cclet.2020.07.017
25. [25]
  V. Nair, B.R. Devi, N. Vidya, et al., Tetrahedron Lett. 45(2004) 3203-3205. doi: 10.1016/j.tetlet.2004.02.132
26. [26]
  V. Nair, B. Rema Devi, L.R. Varma, Tetrahedron Lett. 46(2005) 5333-5335. doi: 10.1016/j.tetlet.2005.06.014
27. [27]
  V. Nair, S. Devipriya, E. Suresh, Tetrahedron 64(2008) 3567-3577. doi: 10.1016/j.tet.2008.01.106
28. [28]
  A. Alizadeh, S.Y. Hosseini, H. Sedighian, et al., Tetrahedron 71(2015) 7885-7891. doi: 10.1016/j.tet.2015.08.033
29. [29]
  V. Nair, A. Deepthi, P.B. Beneesh, et al., Synthesis 9(2006) 1443-1446. doi: 10.1055/s-2006-926423
30. [30]
  H.R. Dong, Z.B. Chen, R.S. Li, et al., RSC Adv. 5(2015) 10768-10772. doi: 10.1039/C4RA14811H
31. [31]
  M.J. Fan, Z.Y. Yan, W.M. Liu, et al., J. Org. Chem. 70(2005) 8204-8207. doi: 10.1021/jo050903g
32. [32]
  M.G. Fan, L.N. Guo, X.Y. Liu, et al., Synthesis 3(2005) 391-396.
33. [33]
  H.F. Gruetzmacher, K. Albrecht, Chem. Ber. 122(1989) 2299-2302. doi: 10.1002/cber.19891221216
34. [34]
  M. Adib, B. Mohammadi, M. Mahdavi, et al., Synlett 16(2007) 2497-2500. doi: 10.1055/s-2007-986657
35. [35]
  H. Mehrabi, M. Hatami-Pour, Chin. Chem. Lett. 25(2014) 1495-1498. doi: 10.1016/j.cclet.2014.05.024
36. [36]
  M.S. Moustafa, S.M. Al-Mousawi, Maghraby Ali Selim, et al., J. Org. Chem. 10(2014) 141-149.
37. [37]
  I. Yavari, M. Sirouspour, S. Souri, Helv. Chim. Acta 93(2010) 2176-2182. doi: 10.1002/hlca.201000082
38. [38]
  A. Alizadeh, S.Y. Hosseini, H. Sedighian, et al., Tetrahedron 71(2015) 7885-7889. doi: 10.1016/j.tet.2015.08.033
39. [39]
  A. Alizadeh, H. Sedighian, F. Bayat, Synlett 25(2014) 389-392.
40. [40]
  A.A. Esmaeili, A. Moradi, H.K. Mohammadi, Tetrahedron 66(2010) 3575-3578. doi: 10.1016/j.tet.2010.03.052
41. [41]
  J. Zhang, W.J. Yang, J. Sun, et al., Eur. J. Org. Chem. 34(2015) 7571-7582.
42. [42]
  E. Hamideh, A.A. Mohammad, Helv. Chim. Acta 96(2013) 2196-2199. doi: 10.1002/hlca.201300041
43. [43]
  F. Auria-Luna, E. Marques-Lopez, R.P. Herrera, Molecules 23(2018) 2692. doi: 10.3390/molecules23102692
44. [44]
  V. Nair, R.S. Menon, P.B. Beneesh, et al., Org. Lett. 6(2004) 767-769. doi: 10.1021/ol036491k
45. [45]
  M. Adib, B. Mohammadi, E. Sheikhi, et al., Chin. Chem. Lett. 22(2011) 314-317. doi: 10.1016/j.cclet.2010.10.032
46. [46]
  H. Mehrabi, H. Tavakolian, J. Chem. Res. 40(2016) 750-752. doi: 10.3184/174751916X14792310135102
47. [47]
  V. Nair, D.B. Rema, A.N. Pillai, et al., Heterocycles 73(2007) 249-254. doi: 10.3987/COM-07-S(U)50
48. [48]
  A.K. Mourad, F.K. Mohammed, G.H. Tammam, et al., J. Heterocycl. Chem. 56(2019) 2262-2273. doi: 10.1002/jhet.3621
49. [49]
  H. Mehrabi, M. Hatami-Pour, Synth. Commun. 43(2013) 611-618. doi: 10.1080/00397911.2011.605240
50. [50]
  V. Nair, P.B. Beneesh, V. Sreekumar, et al., Tetrahedron Lett. 46(2005) 201-203. doi: 10.1016/j.tetlet.2004.11.081
51. [51]
  M.I. Pleshchev, V.Y. Petukhova, V.V. Kuznetsov, et al., Russ. Chem. Bull. 62(2013) 1066-1075. doi: 10.1007/s11172-013-0143-9
52. [52]
  C. Wang, Y.H. Jiang, C.G. Yan, Chin. Chem. Lett. 26(2015) 889-893. doi: 10.1016/j.cclet.2015.05.018
53. [53]
  S. Saito, Y. Yamamoto, Chem. Rev. 100(2000) 2901-2916. doi: 10.1021/cr990281x
54. [54]
  X.J. Yang, L.Y. Yuan, Z.Y. Chen, Org. Lett. 20(2018) 6952-6951. doi: 10.1021/acs.orglett.8b03099
55. [55]
  Q.F. Jia, Y.F. Lan, X. Ye, et al., RSC Adv. 10(2020) 29171-29174. doi: 10.1039/D0RA05251E
56. [56]
  W. Song, S.A. Blaszczyk, J. Liu, et al., Org. Biomol. Chem. 15(2017) 7490-7590. doi: 10.1039/C7OB01000A
57. [57]
  L. Chen, Z. Liu, S. Zhu, Org. Biomol. Chem. 16(2018) 8884-8898. doi: 10.1039/C8OB02348D
58. [58]
  P. Gao, J.J. Liu, Y.Y. Wei, Org. Lett. 15(2013) 2872-2875. doi: 10.1021/ol401206g
59. [59]
  W.M. Shu, K.L. Zheng, J.R. Ma, et al., Org. Lett. 17(2015) 5216-5219. doi: 10.1021/acs.orglett.5b02548
60. [60]
  Q. Zhao, C. Peng, G. Zhan, et al., RSC Adv. 10(2020) 40983-41003. doi: 10.1039/D0RA08068C
61. [61]
  Q.F. Zhou, F. Yang, Q.X. Guo, et al., Synlett (2007) 2073-2076.
62. [62]
  L.H. Zhou, X.Q. Yu, L. Pu, Tetrahedron Lett. 51(2010) 425-427. doi: 10.1016/j.tetlet.2009.11.048
1. [1]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
2. [2]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
3. [3]
  Maomao Liu , Guizeng Liang , Ningce Zhang , Tao Li , Lipeng Diao , Ping Lu , Xiaoliang Zhao , Daohao Li , Dongjiang Yang . Electron-rich Ni2+ in Ni3S2 boosting electrocatalytic CO2 reduction to formate and syngas. Chinese Journal of Structural Chemistry, 2024, 43(8): 100359-100359. doi: 10.1016/j.cjsc.2024.100359
4. [4]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
5. [5]
  Ruowen Liang , Chao Zhang , Guiyang Yan . Enhancing CO2 cycloaddition through ligand functionalization: A case study of UiO-66 metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(2): 100211-100211. doi: 10.1016/j.cjsc.2023.100211
6. [6]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
7. [7]
  Jiangqi Ning , Junhan Huang , Yuhang Liu , Yanlei Chen , Qing Niu , Qingqing Lin , Yajun He , Zheyuan Liu , Yan Yu , Liuyi Li . Alkyl-linked TiO2@COF heterostructure facilitating photocatalytic CO2 reduction by targeted electron transport. Chinese Journal of Structural Chemistry, 2024, 43(12): 100453-100453. doi: 10.1016/j.cjsc.2024.100453
8. [8]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
9. [9]
  Fei Jin , Bolin Yang , Xuanpu Wang , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Facilitating efficient photocatalytic hydrogen evolution via enhanced carrier migration at MOF-on-MOF S-scheme heterojunction interfaces through a graphdiyne (CnH2n-2) electron transport layer. Chinese Journal of Structural Chemistry, 2023, 42(12): 100198-100198. doi: 10.1016/j.cjsc.2023.100198
10. [10]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
11. [11]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
12. [12]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
13. [13]
  Ze-Yuan Ma , Mei Xiao , Cheng-Kun Li , Adedamola Shoberu , Jian-Ping Zou . S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds. Chinese Chemical Letters, 2024, 35(5): 109076-. doi: 10.1016/j.cclet.2023.109076
14. [14]
  Xiuzheng Deng , Yi Ke , Jiawen Ding , Yingtang Zhou , Hui Huang , Qian Liang , Zhenhui Kang . Construction of ZnO@CDs@Co₃O₄ sandwich heterostructure with multi-interfacial electron-transfer toward enhanced photocatalytic CO₂ reduction. Chinese Chemical Letters, 2024, 35(4): 109064-. doi: 10.1016/j.cclet.2023.109064
15. [15]
  Lumin Zheng , Ying Bai , Chuan Wu . Multi-electron reaction and fast Al ion diffusion of δ-MnO₂ cathode materials in rechargeable aluminum batteries via first-principle calculations. Chinese Chemical Letters, 2024, 35(4): 108589-. doi: 10.1016/j.cclet.2023.108589
16. [16]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
17. [17]
  Renshu Huang , Jinli Chen , Xingfa Chen , Tianqi Yu , Huyi Yu , Kaien Li , Bin Li , Shibin Yin . Synergized oxygen vacancies with Mn2O3@CeO2 heterojunction as high current density catalysts for Li–O2 batteries. Chinese Journal of Structural Chemistry, 2023, 42(11): 100171-100171. doi: 10.1016/j.cjsc.2023.100171
18. [18]
  Shengwen Guan , Zhaotong Wei , Ningxu Han , Yude Wei , Bin Xu , Ming Wang , Junjuan Shi . Construction of metallo-complexes with 2,2′:6′,2″-terpyridine substituted triphenylamine in different modified positions and their photophysical properties. Chinese Chemical Letters, 2024, 35(7): 109348-. doi: 10.1016/j.cclet.2023.109348
19. [19]
  Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
20. [20]
  Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe₂O₃/TiO₂ heterojunction for enhanced photo-Fenton activity with low H₂O₂ consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1104)
HTML views(224)

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