Citation: Shaomin Chen, Tianjian Zhang, Zhenhua Xu, Bo You, Minghao Li, Yanlong Gu. A Lewis acid-catalyzed tandem reaction enabling 2-arylglycerol derivative as a versatile 1, 3-biselectrophile for the synthesis of 4H-chromenes and 2-pyridinones[J]. Chinese Chemical Letters, ;2023, 34(9): 108130. doi: 10.1016/j.cclet.2023.108130 shu

A Lewis acid-catalyzed tandem reaction enabling 2-arylglycerol derivative as a versatile 1, 3-biselectrophile for the synthesis of 4H-chromenes and 2-pyridinones

Shaomin Chen ^a ,
Tianjian Zhang ^a ,
Zhenhua Xu ^a ,
Bo You ^a ,
Minghao Li ^{a, *,} ,
Yanlong Gu ^{a, b, c, *,}

a.
Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China
b.
School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832004, China
c.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Lanzhou 730000, China

liminghaochem@hust.edu.cn

klgyl@hust.edu.cn

Received Date: 12 October 2022
Revised Date: 26 December 2022
Accepted Date: 2 January 2023
Available Online: 5 January 2023

Figures(4)

Acid-catalyzed tandem reactions were established by employing a novel class of 2-arylglycerol derivative, 5-aryl-1, 3-dioxan-5-ol, as versatile 1, 3-biselectrophile. In the reactions, 5-aryl-1, 3-dioxan-5-ol works like atropaldehydes or 2-aryl malondialdehydes, and can react with 2-naphthols and β-keto amides, allowing the synthesis of 4H-chromenes and 5-aryl-2-pyridinones. High yields, good functional group tolerance, broad substrate scope and simple reaction operation make this protocol attractive.
- Lewis acid catalysis,
- 2-Arylglycerol derivative,
- 1, 3-Biselectrophile,
- Six-membered heterocycles,
- [3+3] cyclization
1. [1]
  M. Elsherbini, W.S. Hamama, H.H. Zoorob, Coord. Chem. Rev. 330 (2017) 110–126. doi: 10.1016/j.ccr.2016.09.016
2. [2]
  M. Neetha, T. Aneeja, C.M.A. Afsina, G. Anilkumar, ChemCatChem 12 (2020) 5330–5358. doi: 10.1002/cctc.202000719
3. [3]
  L.X. Liang, L.D. Guo, R.B. Tong, Acc. Chem. Res. 55 (2022) 2326–2340. doi: 10.1021/acs.accounts.2c00358
4. [4]
  Preeti, K.N. Singh, Org. Biomol. Chem. 19 (2021) 2622–2657. doi: 10.1039/D1OB00145K
5. [5]
  S. Zou, Z. Zhang, C. Chen, C. Xi, Chin. Chem. Lett. 33 (2022) 3021–3025. doi: 10.1016/j.cclet.2021.12.012
6. [6]
  B. Gu, S. Wu, H. Xu, et al., Chin. Chem. Lett. 32 (2021) 672–675. doi: 10.1016/j.cclet.2020.06.010
7. [7]
  Y. Xia, Q.F. Bao, Y. Li, et al., Chem. Commun. 55 (2019) 4675–4678. doi: 10.1039/C9CC00611G
8. [8]
  Y. Hao, Y. Gong, Z. Cao, Y. Zhou, J. Zhou, Chin. Chem. Lett. 31 (2020) 681–684. doi: 10.1016/j.cclet.2019.08.018
9. [9]
  X. Xu, M.P. Doyle, Acc. Chem. Res. 47 (2014) 1396–1405. doi: 10.1021/ar5000055
10. [10]
  B. Katryniok, H. Kimura, E. Skrzyńska, et al., Green Chem. 13 (2011) 1960–1979. doi: 10.1039/c1gc15320j
11. [11]
  D. Liu, J.C. Liu, W. Cai, et al., Nat. Commun. 10 (2019) 1779. doi: 10.1038/s41467-019-09788-5
12. [12]
  M. Bolduc, J. Bergeron, A. Michaud, et al., Tetrahedron: Asymmetry 23 (2012) 428–433. doi: 10.1016/j.tetasy.2012.04.001
13. [13]
  B. Jung, M.S. Hong, S.H. Kang, Angew. Chem. Int. Ed. 46 (2007) 2616–2618. doi: 10.1002/anie.200604977
14. [14]
  L. Zhao, R.I. Kaiser, W. Lu, et al., Phys. Chem. Chem. Phys. 22 (2020) 15381–15388. doi: 10.1039/D0CP02216K
15. [15]
  Y. Gu, F. Wu, J. Yang, Adv. Syn. Catal. 360 (2018) 2727–2741. doi: 10.1002/adsc.201800462
16. [16]
  M. Jiang, L. Feng, J. Feng, P. Jiao, Org. Lett. 19 (2017) 2210–2213. doi: 10.1021/acs.orglett.7b00558
17. [17]
  S.M. Chen, Z.Y. Chen, T.J. Zhang, et al., Green Chem. 24 (2022) 7376–7381. doi: 10.1039/D2GC02072F
18. [18]
  S. Chen, M. Li, Y. Gu, Chem. Commun. 57 (2021) 10431–10434. doi: 10.1039/D1CC04000F
19. [19]
  H. Dai, S. Yu, W. Cheng, Z.F. Xu, C.Y. Li, Chem. Commun. 53 (2017) 6417–6420. doi: 10.1039/C7CC02521A
20. [20]
  L. Xia, Y.R. Lee, Org. Biomol. Chem. 11 (2013) 5254–5263. doi: 10.1039/c3ob40791h
21. [21]
  J.K. Vandavasi, C. Hsiao, W. Hu, et al., Eur. J. Org. Chem. (2015) 3171–3177 2015. doi: 10.1002/ejoc.201500224
22. [22]
  X. Peng, Y. Wang, K. Sun, et al., J. Nat. Prod. 74 (2011) 1298–1302. doi: 10.1021/np1008976
23. [23]
  M. Ravinder, B. Mahendar, S. Mattapally, et al., Bioorg. Med. Chem. Lett. 22 (2012) 6010–6015. doi: 10.1016/j.bmcl.2012.05.019
24. [24]
  M. Cocco, Eur. J. Med. Chem. 38 (2003) 37–47. doi: 10.1016/S0223-5234(02)00002-8
25. [25]
  E.M. Wallace, J. Lyssikatos, J.F. Blake, et al., J. Med. Chem. 49 (2006) 441–444. doi: 10.1021/jm050834y
26. [26]
  Y. Su, M. Zhao, K. Han, G. Song, X. Li, Org. Lett. 12 (2010) 5462–5465. doi: 10.1021/ol102306c
27. [27]
  L. Ackermann, A.V. Lygin, N. Hofmann, Org. Lett. 13 (2011) 3278–3281. doi: 10.1021/ol201244s
28. [28]
  H.J. Chen, C.Y. Chew, E.H. Chang, et al., J. Am. Chem. Soc. 140 (2018) 5224–5234. doi: 10.1021/jacs.8b01159
1. [1]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
2. [2]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
3. [3]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
4. [4]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
5. [5]
  Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
6. [6]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
7. [7]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
8. [8]
  Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr_1-xZrSi₂O₇∶xDy³⁺ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
9. [9]
  Juan Guo , Mingyuan Fang , Qingsong Liu , Xiao Ren , Yongqiang Qiao , Mingju Chao , Erjun Liang , Qilong Gao . Zero thermal expansion in Cs₂W₃O₁₀. Chinese Chemical Letters, 2024, 35(7): 108957-. doi: 10.1016/j.cclet.2023.108957
10. [10]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
11. [11]
  Yan ZHAO , Jiaxu WANG , Zhonghu LI , Changli LIU , Xingsheng ZHAO , Hengwei ZHOU , Xiaokang JIANG . Gd³⁺-doped Sc₂W3O₁₂: Eu³⁺ red phosphor: Preparation and luminescence performance. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 461-468. doi: 10.11862/CJIC.20240316
12. [12]
  Luyan Shi , Ke Zhu , Yuting Yang , Qinrui Liang , Qimin Peng , Shuqing Zhou , Tayirjan Taylor Isimjan , Xiulin Yang . Phytic acid-derivative Co₂B-CoPO_x coralloidal structure with delicate boron vacancy for enhanced hydrogen generation from sodium borohydride. Chinese Chemical Letters, 2024, 35(4): 109222-. doi: 10.1016/j.cclet.2023.109222
13. [13]
  Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na₃V₂(PO₄)₃ cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
14. [14]
  Xun Zhu , Chenchen Zhang , Yingying Li , Yin Lu , Na Huang , Dawei Wang . Degradation of perfluorooctanoic acid by inductively heated Fenton-like process over the Fe₃O₄/MIL-101 composite. Chinese Chemical Letters, 2024, 35(12): 109753-. doi: 10.1016/j.cclet.2024.109753
15. [15]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
16. [16]
  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
17. [17]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
18. [18]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
19. [19]
  He Yao , Wenhao Ji , Yi Feng , Chunbo Qian , Chengguang Yue , Yue Wang , Shouying Huang , Mei-Yan Wang , Xinbin Ma . Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide. Chinese Chemical Letters, 2025, 36(4): 110076-. doi: 10.1016/j.cclet.2024.110076
20. [20]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(443)
HTML views(18)

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