Skip to main content
SpringerLink
Log in

Synthesis of non-classical heteroaryl C-glycosides via Minisci-type alkylation of N-heteroarenes with 4-glycosyl-dihydropyridines

  • Communications
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

A radical-mediated method was reported for diastereoselective synthesis of non-classical heteroaryl C-glycosides via Minisci-type alkylation of N-heteroarenes with 4-glycosyl-1,4-dihydropyridine (DHP) reagents. These DHP reagents serve as convenient precursors for various glycosyl radicals under the activation of single electron transfer (SET) oxidation by persulfate and visible light irradiation with or without photocatalyst.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Reviews on synthesis and biological application of C-aryl glycosides: Jaramillo C, Knapp S. Synthesis, 1994, 1994(01): 1–20

    Article  Google Scholar 

  2. Bililign T, Griffith BR, Thorson JS. Nat Prod Rep, 2005, 22: 742–760

    Article  CAS  PubMed  Google Scholar 

  3. Frihed TG, Bols M, Pedersen CM. Eur J Org Chem, 2016, 2016(16): 2740–2756

    Article  CAS  Google Scholar 

  4. Yang Y, Yu B. Chem Rev, 2017, 117: 12281–12356

    Article  CAS  PubMed  Google Scholar 

  5. Kitamura K, Ando Y, Matsumoto T, Suzuki K. Chem Rev, 2018, 118: 1495–1598

    Article  CAS  PubMed  Google Scholar 

  6. Aguillón AR, Mascarello A, Segretti ND, de Azevedo HFZ, Guimaraes CRW, Miranda LSM, de Souza ROMA. Org Process Res Dev, 2018, 22: 467–488

    Article  CAS  Google Scholar 

  7. Goodwin NC, Mabon R, Harrison BA, Shadoan MK, Almstead ZY, Xie Y, Healy J, Buhring LM, DaCosta CM, Bardenhagen J, Mseeh F, Liu Q, Nouraldeen A, Wilson AGE, Kimball SD, Powell DR, Rawlins DB. J Med Chem, 2009, 52: 6201–6204

    Article  CAS  PubMed  Google Scholar 

  8. Goodwin NC, Ding ZM, Harrison BA, Strobel ED, Harris AL, Smith M, Thompson AY, Xiong W, Mseeh F, Bruce DJ, Diaz D, Gopinathan S, Li L, O’Neill E, Thiel M, Wilson AGE, Carson KG, Powell DR, Rawlins DB. J Med Chem, 2017, 60: 710–721

    Article  CAS  PubMed  Google Scholar 

  9. Markham A, Keam SJ. Drugs, 2019, 79: 1023–1029

    Article  CAS  PubMed  Google Scholar 

  10. Cheng G, Fan R, Hernàndez-Torres JM, Boulineau FP, Wei A. Org Lett, 2007, 9: 4849–4852

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Bednarski M, Danishefsky S. J Am Chem Soc, 1986, 108: 7060–7067

    Article  CAS  Google Scholar 

  12. Zhdanov YA, Alexeev YE, Dorofeenko GN. Carbohydr Res, 1968, 8: 121–122

    Article  CAS  Google Scholar 

  13. Saha NN, Desai VN, Dhavale DD. J Org Chem, 1999, 64: 1715–1719

    Article  CAS  PubMed  Google Scholar 

  14. Reddy BVS, Majumder N, Sridhar B. Tetrahedron Lett, 2014, 55: 6081–6084

    Article  CAS  Google Scholar 

  15. Zhang F, Xi Y, Lu Y, Wang L, Liu L, Li J, Zhao Y. Chem Commun, 2014, 50: 5771–5773

    Article  CAS  Google Scholar 

  16. Mondal RR, Khamarui S, Maiti DK. ACS Omega, 2016, 1: 251–263

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Liu H, Liang Y, Jia TT, Han F, Zhang F, Zhao Y. Eur J Org Chem, 2017, 2017(11): 1443–1449

    Article  CAS  Google Scholar 

  18. Zhang F, Li Y, Gao F, Liu H, Zhao Y. Carbohydr Res, 2019, 477: 39–50

    Article  CAS  PubMed  Google Scholar 

  19. Vismara E, Torri G, Pastori N, Marchiandi M. Tetrahedron Lett, 1992, 33: 7575–7578

    Article  CAS  Google Scholar 

  20. Kuwana D, Ovadia B, Kamimura D, Nagatomo M, Inoue M. Asian J Org Chem, 2019, 8: 1088–1091

    Article  CAS  Google Scholar 

  21. For a review on glycosylation with classical glycosyl radicals: Togo H, He W, Waki Y, Yokoyama M. Synlett, 1998, 1998(7): 700–717

    Article  Google Scholar 

  22. For synthesis of classical C-Aryl glycosides with glycosyl radicals: Togo H, Fujii M, Ikuma T, Yokoyama M. Tetrahedron Lett, 1991, 32: 3377–3380

    Article  CAS  Google Scholar 

  23. He W, Togo H, Waki Y, Yokoyama M. J Chem Soc Perkin Trans 1, 1998, 2425–2434

  24. Adak L, Kawamura S, Toma G, Takenaka T, Isozaki K, Takaya H, Orita A, Li HC, Shing TKM, Nakamura M. J Am Chem Soc, 2017, 139: 10693–10701

    Article  CAS  PubMed  Google Scholar 

  25. Ma Y, Liu S, Xi Y, Li H, Yang K, Cheng Z, Wang W, Zhang Y. Chem Commun, 2019, 55: 14657–14660

    Article  CAS  Google Scholar 

  26. Liu J, Lei C, Gong H. Sci China Chem, 2019, 62: 1492–1496

    Article  CAS  Google Scholar 

  27. For recent synthesis of non-classical C-Aryl glycosides with non-classical glycosyl radicals: Zhou X, Wang P, Zhang L, Chen P, Ma M, Song N, Ren S, Li M. J Org Chem, 2018, 83: 588–603

    Article  CAS  PubMed  Google Scholar 

  28. Wang Y, Yang L, Liu S, Huang L, Liu Z-. Adv Synth Catal, 2019, 361: 4568–4574

    Article  CAS  Google Scholar 

  29. Dumoulin A, Matsui JK, Gutiérrez-Bonet Á, Molander GA. Angew Chem Int Ed, 2018, 57: 6614–6618

    Article  CAS  Google Scholar 

  30. For reviews on hydrogenation using 1,4-dihydropyridine as hydride donor, see: Ouellet SG, Walji AM, MacMillan DWC. Acc Chem Res, 2007, 40: 1327–1339

    Article  CAS  PubMed  Google Scholar 

  31. Zheng C, You SL. Chem Soc Rev, 2012, 41: 2498–2518

    Article  CAS  PubMed  Google Scholar 

  32. For recent reviews on alkylation reaction using 4-alkyl-1,4-dihy-dropyridine as alkyl donor: Huang W, Cheng X. Synlett, 2016, 28: 148–158

    Article  CAS  Google Scholar 

  33. Ye S, Wu J. Acta Chim Sin, 2019, 77: 814–831

    Article  CAS  Google Scholar 

  34. For early examples on dealkylative aromatization of 4-alkyl-1,4-dihydropyridines: Loev B, Snader KM. J Org Chem, 1965, 30: 1914–1916

    Article  CAS  Google Scholar 

  35. Lee JS, Jacobsen NE, Ortiz de Montellano PR. Biochemistry, 1988, 27: 7703–7710

    Article  CAS  PubMed  Google Scholar 

  36. Zhang D, Wu LZ, Zhou L, Han X, Yang QZ, Zhang LP, Tung CH. J Am Chem Soc, 2004, 126: 3440–3441

    Article  CAS  PubMed  Google Scholar 

  37. Fang X, Liu YC, Li C. J Org Chem, 2007, 72: 8608–8610

    Article  CAS  PubMed  Google Scholar 

  38. For the synthesis of 4-alkyl-1,4-dihydropyridines: Tewari N, Dwivedi N, Tripathi RP. Tetrahedron Lett, 2004, 45: 9011–9014

    Article  CAS  Google Scholar 

  39. Lu L, Xu H, Zhou P, Yu F. Chin J Org Chem, 2016, 36: 2858–2879

    Article  CAS  Google Scholar 

  40. Li G, Chen R, Wu L, Fu Q, Zhang X, Tang Z. Angew Chem Int Ed, 2013, 52: 8432–8436

    Article  CAS  Google Scholar 

  41. Nakajima K, Nojima S, Nishibayashi Y. Angew Chem Int Ed, 2016, 55: 14106–14110

    Article  CAS  Google Scholar 

  42. Nakajima K, Nojima S, Sakata K, Nishibayashi Y. ChemCatChem, 2016, 8: 1028–1032

    Article  CAS  Google Scholar 

  43. Buzzetti L, Prieto A, Roy SR, Melchiorre P. Angew Chem Int Ed, 2017, 56: 15039–15043

    Article  CAS  Google Scholar 

  44. Chen W, Liu Z, Tian J, Li J, Ma J, Cheng X, Li G. J Am Chem Soc, 2016, 138: 12312–12315

    Article  CAS  PubMed  Google Scholar 

  45. Li G, Wu L, Lv G, Liu H, Fu Q, Zhang X, Tang Z. Chem Commun, 2014, 50: 6246–6248

    Article  CAS  Google Scholar 

  46. McDonald BR, Scheidt KA. OrgLett, 2018, 20: 6877–6881

    CAS  Google Scholar 

  47. Nakajima K, Guo X, Nishibayashi Y. Chem Asian J, 2018, 13: 3653–3657

    Article  CAS  PubMed  Google Scholar 

  48. Verrier C, Alandini N, Pezzetta C, Moliterno M, Buzzetti L, Hepburn HB, Vega-Peñaloza A, Silvi M, Melchiorre P. ACS Catal, 2018, 8: 1062–1066

    Article  CAS  Google Scholar 

  49. van Leeuwen T, Buzzetti L, Perego LA, Melchiorre P. Angew Chem Int Ed, 2019, 58: 4953–4957

    Article  CAS  Google Scholar 

  50. Liu X, Liu R, Dai J, Cheng X, Li G. Org Lett, 2018, 20: 6906–6909

    Article  CAS  PubMed  Google Scholar 

  51. Song ZY, Zhang CL, Ye S. Org Biomol Chem, 2018, 17: 181–185

    Article  PubMed  Google Scholar 

  52. Chen X, Ye F, Luo X, Liu X, Zhao J, Wang S, Zhou Q, Chen G, Wang P. J Am Chem Soc, 2019, 141: 18230–18237

    Article  CAS  PubMed  Google Scholar 

  53. Liang S, Kumon T, Angnes RA, Sanchez M, Xu B, Hammond GB. Org Lett, 2019, 21: 3848–3854

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  54. Nakajima K, Zhang Y, Nishibayashi Y. OrgLett, 2019, 21: 4642–4645

    CAS  Google Scholar 

  55. Xie S, Li D, Huang H, Zhang F, Chen Y. J Am Chem Soc, 2019, 141: 16237–16242

    Article  CAS  PubMed  Google Scholar 

  56. For enantioselective alkylation with 4-alkyl-1,4-dihydropyridines: de Assis FF, Huang X, Akiyama M, Pilli RA, Meggers E. J Org Chem, 2018, 83: 10922–10932

    Article  CAS  PubMed  Google Scholar 

  57. Zhang HH, Zhao JJ, Yu S. J Am Chem Soc, 2018, 140: 16914–16919

    Article  CAS  PubMed  Google Scholar 

  58. Zhang K, Lu LQ, Jia Y, Wang Y, Lu FD, Pan F, Xiao WJ. Angew Chem Int Ed, 2019, 58: 13375–13379

    Article  CAS  Google Scholar 

  59. Gandolfo E, Tang X, Raha Roy S, Melchiorre P. Angew Chem Int Ed, 2019, 58: 16854–16858

    Article  CAS  Google Scholar 

  60. For acylation reactions with 4-acyl-DHPs: Bieszczad B, Perego LA, Melchiorre P. Angew Chem Int Ed, 2019, 58: 16878–16883

    Article  CAS  Google Scholar 

  61. Goti G, Bieszczad B, Vega-Peñaloza A, Melchiorre P. Angew Chem Int Ed, 2019, 58: 1213–1217

    Article  CAS  Google Scholar 

  62. Gutiérrez-Bonet Á, Tellis JC, Matsui JK, Vara BA, Molander GA. ACS Catal, 2016, 6: 8004–8008

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  63. Gutiérrez-Bonet Á, Remeur C, Matsui JK, Molander GA. J Am Chem Soc, 2017, 139: 12251–12258

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  64. Badir SO, Dumoulin A, Matsui JK, Molander GA. Angew Chem Int Ed, 2018, 57: 6610–6613

    Article  CAS  Google Scholar 

  65. Phelan JP, Lang SB, Sim J, Berritt S, Peat AJ, Billings K, Fan L, Molander GA. J Am Chem Soc, 2019, 141: 3723–3732

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  66. For selected reviews on C-nucleosides: Ferrero M, Gotor V. Chem Rev, 2000, 100: 4319–4348

    Article  CAS  PubMed  Google Scholar 

  67. Wu Q, Simons C. Synthesis, 2004, 2004(10): 1533

    Article  CAS  Google Scholar 

  68. Bokor É, Kun S, Goyard D, Tóth M, Praly JP, Vidal S, Somsàk L. Chem Rev, 2017, 117: 1687–1764

    Article  CAS  PubMed  Google Scholar 

  69. Stambaský J, Hocek M, Kocovský P. Chem Rev, 2009, 109: 6729–6764

    Article  PubMed  CAS  Google Scholar 

  70. De Clercq E. J Med Chem, 2016, 59: 2301–2311

    Article  CAS  PubMed  Google Scholar 

  71. Temburnikar K, Seley-Radtke KL. Beilstein J Org Chem, 2018, 14: 772–785

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  72. Shiraishi T, Kuzuyama T. J Antibiot, 2019, 72: 913–923

    Article  CAS  Google Scholar 

  73. The stereochemistry was assigned via 2-D 1H NMR analysis (See Supporting Information for details)

  74. We believe the stereoselectivity of this Minisci-type alkylation reaction originated from a combined effect of stereoelectronic and steric interactions. Anomeric effect and quasi-anomeric stabilization make the anomeric radical prefer to adopt axial conformation, and the N-heterocycles would approach the radical intermediates from less hindered face (See Supporting Information for details)

  75. Gu F, Huang W, Liu X, Chen W, Cheng X. Adv Synth Catal, 2018, 360: 925–931

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21672105, 21725204, 91753124), Natural Science Foundation of Tianjin (17JCYBJC19700, 18JCZDJC32800), and the Fundamental Research Funds for the Central Universities (Nankai University) (63191746).

Author information

Authors and Affiliations

  1. State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, China

    Qingbing Wang, Juan Duan, Pingping Tang, Gong Chen & Gang He

Authors
  1. Qingbing Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Juan Duan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pingping Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Gong Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Gang He
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Gong Chen or Gang He.

Additional information

Conflict of interest

The authors declare no conflict of interest.

Supporting information

The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

Supporting Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, Q., Duan, J., Tang, P. et al. Synthesis of non-classical heteroaryl C-glycosides via Minisci-type alkylation of N-heteroarenes with 4-glycosyl-dihydropyridines. Sci. China Chem. 63, 1613–1618 (2020). https://doi.org/10.1007/s11426-020-9813-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-020-9813-5

Search

Navigation