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
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