Citation: Ya Wang, Shiqiang Mu, Xin Li, Qiuling Song. [4 + 1] Cyclization of benzohydrazide and ClCF₂COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d₅[J]. Chinese Chemical Letters, ;2022, 33(3): 1511-1514. doi: 10.1016/j.cclet.2021.08.089 shu

[4 + 1] Cyclization of benzohydrazide and ClCF₂COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d₅

Ya Wang ^a ,
Shiqiang Mu ^a ,
Xin Li ^a ,
Qiuling Song ^{a, b, c, *,}

a.
Institute of Next Generation Matter Transformation, College of Materials Science & Engineering and College of Chemical Engineering at Huaqiao University, Xiamen 361021, China
b.
Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China
c.
State Key Laboratory of Organometallic Chemistry and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

qsong@hqu.edu.cn

Received Date: 14 June 2021
Revised Date: 13 August 2021
Accepted Date: 16 August 2021
Available Online: 23 August 2021

Figures(8)

A facile synthesis of 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d₅ via [4 + 1] cyclization of ClCF₂COONa with non-amine compounds containing amino groups is developed. Of note, this is the first time that halofluorinated compounds are used as C1 synthon to construct deuterated nitrogen-heterocyclic compounds. The current protocol features simple operation, readily accessible raw materials, wide substrate scope and valuable products
- Transition-metal-free catalyzed,
- [4 + 1] Cyclization,
- Halofluorinated compounds,
- 1,3,4-Oxadiazoles
1. [1]
  X. Ma, Q. Song, Chem. Soc. Rev. 49 (2020) 9197-9219. doi: 10.1039/D0CS00604A
2. [2]
  P.K. Mykhailiuk, Chem. Rev. 120 (2020) 12718-12755. doi: 10.1021/acs.chemrev.0c00406
3. [3]
  M. Wang, Z. Shi, Chem. Rev. 120 (2020) 7348-7398. doi: 10.1021/acs.chemrev.9b00384
4. [4]
  S. Zhu, L. Chu, Chin. J. Org. Chem. 40 (2020) 3980-3981. doi: 10.6023/cjoc202000078
5. [5]
  L. Lv, C.J. Li, Angew. Chem. Int. Ed. 60 (2021) 13098-13104. doi: 10.1002/anie.202102240
6. [6]
  Y. Ning, X. Zhang, X. Bi, Angew. Chem. Int. Ed. 59 (2020) 6473-6481. doi: 10.1002/anie.202000119
7. [7]
  Y. Ning, P. Sivaguru, X. Bi, et al., Chemistry 6 (2020) 486-496. doi: 10.1016/j.chempr.2019.12.004
8. [8]
  Z. Kuang, H. Chen, Q. Song, et al., Chemistry 6 (2020) 2347-2363. doi: 10.1016/j.chempr.2020.06.034
9. [9]
  J. Su, X. Hu, Q. Song, et al., Nat. Commun. 12 (2021) 4986. doi: 10.1038/s41467-021-25313-z
10. [10]
  H. Luo, Y. Zhao, Z. Shi, et al., Green Synth. Catal. 1 (2020) 26-41. doi: 10.1016/j.gresc.2020.05.006
11. [11]
  X. Ma, X. Yu, Q. Song, et al., Org. Lett. 22 (2020) 5284-5288. doi: 10.1021/acs.orglett.0c01275
12. [12]
  S. Deng, H. Chen, Q. Song, et al., Chem. Sci. 10 (2019) 6828-6833. doi: 10.1039/C9SC01333D
13. [13]
  J. Su, X. Ma, Q. Song, et al., ACS Cent. Sci. 6 (2020) 1819-1826. doi: 10.1021/acscentsci.0c00779
14. [14]
  C. Yu, X. Ma, Q. Song, Org. Chem. Front. 7 (2020) 2950-2954. doi: 10.1039/D0QO00775G
15. [15]
  Y. Wang, Y. Zhou, Q. Song, Chem. Commun. 56 (2020) 6106-6109. doi: 10.1039/D0CC01919D
16. [16]
  X. Liu, H. Sheng, Q. Song, Org. Lett. 23 (2021) 2543-2547. doi: 10.1021/acs.orglett.1c00467
17. [17]
  X. Yu, Y. Zhou, Q. Song, et al., Chem. Commun. 55 (2019) 8079-8082. doi: 10.1039/C9CC03534F
18. [18]
  Y. Wang, Y. Zhou, Q. Song, et al., Org. Lett. 23 (2021) 5599-5604 doi:. doi: 10.1021/acs.orglett.1c01484
19. [19]
  G. Zhang, Q. Shi, Q. Song, et al., CCS Chem. 3 (2021), doi: 10.31635/ccschem.021.202100979. doi: 10.31635/ccschem.021.202100979
20. [20]
  J. Xu, Z. Kuang, Q. Song, Chin. Chem. Lett. 6 (2017) 963-966.
21. [21]
  M. Ke, Q. Song, J. Org. Chem. 81 (2016) 3654-3664. doi: 10.1021/acs.joc.6b00324
22. [22]
  X. Ma, S. Mai, Q. Song, et al., Chem. Commun. 54 (2018) 8960-8963. doi: 10.1039/C8CC04298E
23. [23]
  X. Ma, S. Deng, Q. Song, Org. Chem. Front. 5 (2018) 3505-3509. doi: 10.1039/C8QO00727F
24. [24]
  X. Ma, Y. Zhou, Q. Song, Org. Lett. 20 (2018) 4777-4781. doi: 10.1021/acs.orglett.8b01888
25. [25]
  R. Cheng, Y. Sang, X. Zhang, et al., Angew. Chem. Int. Ed. 60 (2021) 12386-12391. doi: 10.1002/anie.202015921
26. [26]
  S. Zhou, Z.Y. Sun, G. Wang, et al., Org. Lett. 23 (2021) 2205-2211. doi: 10.1021/acs.orglett.1c00352
27. [27]
  M. Zhou, H.Y. Zhao, X. Zhang, et al., J. Am. Chem. Soc. 142 (2020) 18191-18199. doi: 10.1021/jacs.0c08708
28. [28]
  Q. Wang, C. Ni, J. Hu, et al., Angew. Chem. Int. Ed. 59 (2020) 8507-8511. doi: 10.1002/anie.202002409
29. [29]
  J. Liu, W. Ding, W.J. Xiao, et al., Org. Lett. 20 (2018) 461-464. doi: 10.1021/acs.orglett.7b03826
30. [30]
  H. Liang, R. Liu, J. Hu, et al., Org. Lett. 22 (2020) 7047-7051. doi: 10.1021/acs.orglett.0c02688
31. [31]
  S. Rapolu, M. Alla, M. Reddy, et al., Eur. J. Med. Chem. 66 (2013) 91-100. doi: 10.1016/j.ejmech.2013.05.024
32. [32]
  J.T. Palmer, B.L. Hirschbein, G. Wesolowski, et al., Bioorg. Med. Chem. Lett. 16 (2006) 2909-2914. doi: 10.1016/j.bmcl.2006.03.001
33. [33]
  Q. Gao, S. Liu, A. Wu, et al., Org. Lett. 17 (2015) 2960-2963. doi: 10.1021/acs.orglett.5b01241
34. [34]
  T. Kawano, K. Hirano, M. Miura, et al., J. Am. Chem. Soc. 132 (2010) 6900-6901. doi: 10.1021/ja101939r
35. [35]
  J. Hédouin, C. Schneider, C. Hoarau, et al., Org. Lett. 20 (2018) 6027-6032. doi: 10.1021/acs.orglett.8b02365
36. [36]
  L.H. Zou, J. Reball, C. Bolm, et al., Chem. Commun. 48 (2012) 11307-11309. doi: 10.1039/c2cc36711d
37. [37]
  J. Dong, X. Wang, Q. Wang, et al., Chem. Sci. 11 (2020) 1026-1031. doi: 10.1039/C9SC05132E
38. [38]
  C. Schmidt, Nat. Biotechnol. 35 (2017) 493-494. doi: 10.1038/nbt0617-493
39. [39]
  Y. Zhou, L. Lin, Q. Song, et al., Org. Lett. 21 (2019) 7630-7634. doi: 10.1021/acs.orglett.9b02933
40. [40]
  S. Wang, K. Wang, F. Ji, et al., Adv. Synth. Catal. 361 (2019) 3986-3990. doi: 10.1002/adsc.201900395
41. [41]
  A.V. Aksenov, V. Khamraev, M. Rubin, et al., RSC Adv. 9 (2019) 6636-6642. doi: 10.1039/C9RA00976K
1. [1]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
2. [2]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
3. [3]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
4. [4]
  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
5. [5]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
6. [6]
  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
7. [7]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
8. [8]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
9. [9]
  Yin-Hang Chai , Li-Long Dang . New structural breakthrough and topological transformation of homogeneous metalla[4]catenane compounds. Chinese Journal of Structural Chemistry, 2024, 43(10): 100322-100322. doi: 10.1016/j.cjsc.2024.100322
10. [10]
  Qingyun Hu , Wei Wang , Junyuan Lu , He Zhu , Qi Liu , Yang Ren , Hong Wang , Jian Hui . High-throughput screening of high energy density LiMn_1-xFe_xPO₄ via active learning. Chinese Chemical Letters, 2025, 36(2): 110344-. doi: 10.1016/j.cclet.2024.110344
11. [11]
  Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO₄⁻, ReO₄⁻). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
12. [12]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
13. [13]
  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
14. [14]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
15. [15]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
16. [16]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
17. [17]
  Yan Zhu , Jia Liu , Meiheng Lv , Tingting Wang , Dongxiang Zhang , Rong Shang , Xin-Dong Jiang , Jianjun Du , Guiling Wang . Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation. Chinese Chemical Letters, 2024, 35(10): 109446-. doi: 10.1016/j.cclet.2023.109446
18. [18]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
19. [19]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
20. [20]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(604)
HTML views(92)

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

[4 + 1] Cyclization of benzohydrazide and ClCF2COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5

Metrics

通讯作者: 陈斌, bchen63@163.com

[4 + 1] Cyclization of benzohydrazide and ClCF₂COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d₅