Download PDF
Synthesis 2023; 55(17): 2683-2690
DOI: 10.1055/a-2067-4099
paper

Cu(OTf)2/TBHP/O2-Mediated Tandem Oxidative Reaction: Easy Access to Benzopyrano[4,3-b]pyridines

Dongping Cheng∗
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Hongjiao Yang
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Hongshuang Xia
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Huafang Gu
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Jing-Hua Li∗
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Xiaoliang Xu∗
b   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (22078300).
› Further Information
    Permissions and Reprints All articles of this category


Abstract

An effective tandem reaction of 4-aminocoumarins and 1,3-diarylpropenes mediated by Cu(OTf)2/TBHP (tert-butyl hydroperoxide)/O2 that provides various benzopyrano[4,3-b]pyridines in moderate to good yields is disclosed. The reaction proceeds through oxidative coupling, intramolecular cyclization, and dehydro-aromatization. This approach has the advantages of high atom-economy, environmental compatibility, and wide substrate scope.

Key words

tandem reaction - oxidative coupling - TBHP - 4-aminocoumarin - benzopyrano[4,3-b]pyridines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2067-4099.
  • Supporting Information


Publication History

Received: 07 February 2023

Accepted after revision: 31 March 2023

Accepted Manuscript online:
31 March 2023

Article published online:
08 May 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Yang M, Xi Q, Jia W, Wang X. Bioorg. Med. Chem. Lett. 2019; 29: 126758
      CrossrefPubMed
    • 1b Guan A, Liu C, Sun X, Xie Y, Wang M. Bioorg. Med. Chem. 2016; 24: 342
      CrossrefPubMed
    • 1c Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
      CrossrefPubMed
    • 1d Su S, Chiba T, Takeda T, Kido J. Adv. Mater. 2008; 20: 2125
      Crossref
    • 1e Michael JP. Nat. Prod. Rep. 2007; 24: 223
      CrossrefPubMed
    • 1f Lee HW, Kim BY, Ahn JB, Kang SK, Lee JH, Shin JS, Ahn SK, Lee SJ, Yoon SS. Eur. J. Med. Chem. 2005; 40: 862
      CrossrefPubMed
    • 1g Knip M, Douek IF, Moore WP. T, Gillmor HA, McLean AE. M, Bingley PJ, Gale EA. M. Diabetologia 2000; 43: 1337
      CrossrefPubMed
  • 2 Scott GK, Benz CC. WO 077632 A2, 2016
    PubMed
  • 3 Martín-Encinas E, Rubiales G, Knudssen BR, Palacios F, Alonso C. Eur. J. Med. Chem. 2019; 178: 752
    CrossrefPubMed
  • 4 Adib M, Peytam F, Rahmanian-Jazi M, Mohammadi-Khanaposhtani M, Mahernia S, Bijanzadeh HR, Jahani M, Imanparast S, Faramarzi MA, Mahdavi M, Larijani B. New J. Chem. 2018; 42: 17268
    Crossref
  • 5 Hamama WS, Ibrahim ME, Metwalli AE, Zoorob HH. Med. Chem. Res. 2014; 23: 2615
    CrossrefPubMed
  • 6 Patel MA, Bhila VG, Patel NH, Patel AK, Brahmbhatt DI. Med. Chem. Res. 2012; 21: 4381
    CrossrefPubMed
  • 7 Mulakayala N, Rambabu D, Raja MR, Chaitanya M, Kumar CS, Kalle AM, Krishna GR, Reddy CM, Rao MV. B, Pal M. Bioorg. Med. Chem. 2012; 20: 759
    CrossrefPubMed
  • 8 Tao X, Dai J, Zhou J, Xu J, Xu H. Chem. Eur. J. 2018; 24: 6932
    CrossrefPubMed
  • 9 Nealmongkol P, Tangdenpaisal K, Sitthimonchai S, Ruchirawat S, Thasana N. Tetrahedron 2013; 69: 9277
    CrossrefPubMed
  • 10 Demuner AJ, Barbosa LC. A, Miranda AC. M, Geraldo GC, da Silva CM, Giberti S, Bertazzini M, Forlani G. J. Nat. Prod. 2013; 76: 2234
    CrossrefPubMed
  • 11 Vishnumurthy K, Makriyannis A. J. Comb. Chem. 2010; 12: 664
    CrossrefPubMed
  • 12 Ling F, Xiao L, Fang L, Lv Y, Zhong W. Adv. Synth. Catal. 2018; 360: 444
    Crossref
  • 13 Beccalli EM, Contini A, Trimarco P. Tetrahedron Lett. 2004; 45: 3447
    CrossrefPubMed
  • 14 Cheng D, Deng Z, Yan X, Wang M, Xu X, Yan J. Adv. Synth. Catal. 2019; 361: 5025
    CrossrefPubMed
  • 15 Zhang J, Xiao D, Tan H, Liu W. J. Org. Chem. 2020; 85: 3929
    CrossrefPubMed

      • Represented papers:
    • 16a Bjerg EE, Marchán-García J, Buxaderas E, Moglie Y, Radivoy G. J. Org. Chem. 2022; 87: 13480
      CrossrefPubMed
    • 16b Li Q, Li L, Xu Q.-L, Pan F. Org. Lett. 2022; 24: 4292
      CrossrefPubMed
    • 16c Zhao Y, Wang J.-L, Zhang Z, Li X.-S, Niu Z.-J, Liu X.-Y. J. Org. Chem. 2021; 86: 18056
      CrossrefPubMed
    • 16d Almasalma AA, Mejia E. Synthesis 2020; 52: 2613
      Article in Thieme Connect
    • 16e Li H, Feng H, Zhang J, Van der Eycken EV, Huang L. J. Org. Chem. 2019; 84: 10501
      CrossrefPubMed
    • 16f Kantam ML, Gadipelly C, Deshmukh G, Reddy KR, Bhargava S. Chem. Rec. 2019; 19: 1302
      CrossrefPubMed
    • 17a Clinton CD, Prasad DCh, Khanal HD, Lee YR. Asian J. Org. Chem. 2021; 10: 241
      Crossref
    • 17b Xiong M.-F, Ali A, Akram W, Zhang H, Si L.-P, Liu H.-Y. Catal. Commun. 2019; 125: 93
      Crossref
    • 17c Almasalma AA, Mejía E. Chem. Eur. J. 2018; 24: 12269
      CrossrefPubMed
    • 17d Sugiishi T, Nakamura H. J. Am. Chem. Soc. 2012; 134: 2504
      CrossrefPubMed
    • 17e Li C.-J. Acc. Chem. Res. 2009; 42: 335
      CrossrefPubMed
    • 17f Dubs C, Hamashima Y, Sasamoto N, Seidel TM, Suzuki S, Hashizume D, Sodeoka M. J. Org. Chem. 2008; 73: 5859
      CrossrefPubMed
    • 17g Zhao L, Li C.-J. Angew. Chem. Int. Ed. 2008; 47: 7075
      CrossrefPubMed
    • 17h Li Z, Li C.-J. J. Am. Chem. Soc. 2006; 128: 56
      CrossrefPubMed
    • 17i Li Z, Li C.-J. J. Am. Chem. Soc. 2005; 127: 6968
      CrossrefPubMed
    • 18a Boess E, Van Hoof M, Birdsall SL, Klussmann M. J. Org. Chem. 2020; 85: 1972
      CrossrefPubMed
    • 18b Zhu X, Lu Q, Wang X, Zhang T, Hao W, Tu S, Jiang B. J. Org. Chem. 2018; 83: 9890
      CrossrefPubMed
    • 18c Boess E, Wolf LM, Malakar S, Salamone M, Bietti M, Thiel W, Klussmann M. ACS Catal. 2016; 6: 3253
      Crossref
    • 18d Girard SA, Knauber T, Li C. Angew. Chem. Int. Ed. 2014; 53: 74
      CrossrefPubMed
    • 18e Ratnikov MO, Doyle MP. J. Am. Chem. Soc. 2013; 135: 1549
      CrossrefPubMed
    • 19a Mutai P, Breuzard G, Pagano A, Allegro D, Peyrot V, Chibale K. Bioorg. Med. Chem. 2017; 25: 1652
      CrossrefPubMed
    • 19b Hua C, Zhang K, Xin M, Ying T, Gao J, Jia J, Li Y. RSC Adv. 2016; 6: 49221
      Crossref
    • 20a Wang J, Huang W, Zhang Z, Xiang X, Liu R, Zhou X. J. Org. Chem. 2009; 74: 3299
      CrossrefPubMed
    • 20b Yang Z, Tang P, Gauuan JF, Molino BF. J. Org. Chem. 2009; 74: 9546
      CrossrefPubMed