Skip to main content
SpringerLink
Log in

One-pot synthesis of 2,3-diphenyl-6,7-dihydroimidazo[1,2-f]phenanthridin-8(5H)-ones catalyzed by CuI/l-proline

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

2-(2-Bromophenyl)-4,5-diphenyl-1H-imidazole was used as an aryl halide to underwent α-arylation with 1,3-cyclohexanedione first, and then a nucleophilic addition and dehydration to give 2,3-diphenyl-6,7-dihydroimidazo[1,2-f]phenanthridin-8(5H)-one derivatives in good yields. This one-pot CuI-catalyzed procedure provided an efficient method for the synthesis of fused tetracyclic heterocycles containing both imidazole and phenanthridine moieties.

Graphical abstract

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

Fig. 1

Similar content being viewed by others

References

  1. Zhan G, Qu X, Liu J, Tong Q, Zhou J, Sun B, Yao G (2016) Sci Rep 6:33990

    Article  CAS  Google Scholar 

  2. Tang ZH, Cao WX, Wang ZY, Lu JH, Liu B, Chen X, Lu JJ (2017) Redox Biol 12:367

    Article  CAS  Google Scholar 

  3. Ou X, Lu Y, Liao L, Li D, Liu L, Liu H, Xu H (2015) Oncol Rep 33:1264

    Article  CAS  Google Scholar 

  4. Liu Z, Chang S, Guan X, Han N, Yin J (2016) J Chromatogr B 1033–1034:226

    Article  Google Scholar 

  5. Oppolzer W, Keller K (1971) J Am Chem Soc 93:3836

    Article  CAS  Google Scholar 

  6. Jahn S, Seiwert B, Kretzing S, Abraham G, Regenthal R, Karst U (2012) Anal Chim Acta 756:60

    Article  CAS  Google Scholar 

  7. Ramkumar N, Nagarajan R (2015) Org Biomol Chem 13:11046

    Article  CAS  Google Scholar 

  8. Castillo JC, Quiroga J, Abonia R, Rodriguez J, Coquerel Y (2015) Org Lett 17:3374

    Article  CAS  Google Scholar 

  9. Ito M, Konno F, Kumamoto T, Suzuki N, Kawahata M, Yamaguchi K, Ishikawa T (2011) Tetrahedron 67:8041

    Article  CAS  Google Scholar 

  10. Tohyama S, Choshi T, Matsumoto K, Yamabuki A, Hieda Y, Nobuhiro J, Hibino S (2010) Heterocycles 82:397

    Article  CAS  Google Scholar 

  11. Ramani P, Fontana G (2008) Tetrahedron Lett 49:5262

    Article  CAS  Google Scholar 

  12. Brooks J, Szigethy G, Morello G, Deng J, Djurovich PI, Chen HF (2016) Organic electroluminescent device materials based on metal complexes with imidazophenanthridine ligands and organic light-emitting devices using them. U. S. Patent 2016072082 A1, Mar 10, 2016

  13. Brooks J, Szigethy G, Morello G, Deng J, Djurovich PI, Chen HF (2016) Chem Abstr 164:403128

    Google Scholar 

  14. Brooks J, Szigethy G, Morello G, Deng J, Djurovich PI (2015) Compounds with imidazophenanthridine skeletons and complexes formed from the compounds and organic light-emitting devices using the complexes. PCT Int. Appl. WO 2015171627 A1, Nov 12, 2015

  15. Brooks J, Szigethy G, Morello G, Deng J, Djurovich PI (2015) Chem Abstr 163:712160

    Google Scholar 

  16. Steudel A (2015) Light-emitting compound. GB Patent 2520738 A, Jun 3, 2015

  17. Steudel A (2015) Chem Abstr 163:51871

    Google Scholar 

  18. Gulbrandsen HS, Alfaro JLD, Read ML, Gundersen LL (2017) Eur J Org Chem:2305

  19. Saini HK, Dhiman S, Pericherla K, Kumar A (2015) Synthesis 47:3727

    Article  CAS  Google Scholar 

  20. Richmond CJ, Eadie RM, Parenty ADC, Cronin L (2009) J Org Chem 74:8196

    Article  CAS  Google Scholar 

  21. Parenty ADC, Guthrie KM, Song YF, Smith LV, Burkholder E, Cronin L (2006) Chem Commun 1194

  22. Parenty ADC, Smith LV, Pickering AL, Long DL, Cronin L (2004) J Org Chem 69:5934

    Article  CAS  Google Scholar 

  23. Chen DS, Dou GL, Li YL, Liu Y, Wang XS (2013) J Org Chem 78:5700

    Article  CAS  Google Scholar 

  24. Feng BB, Liu JQ, Wang XS (2017) J Org Chem 82:1817

    Article  CAS  Google Scholar 

  25. Li C, Zhang WT, Wang XS (2014) J Org Chem 79:5847

    Article  CAS  Google Scholar 

  26. Liu JQ, Ma YG, Zhang MM, Wang XS (2017) J Org Chem 82:4918

    Article  CAS  Google Scholar 

  27. Esmaeilpour M, Javidi J, Dehghani F, Zahmatkesh S (2017) Res Chem Intermed 4:163

    Article  Google Scholar 

Download references

Acknowledgements

We are grateful to the Major Natural Science Foundation of Jiangsu Province (14KJA150004) and a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions for financial support.

Author information

Authors and Affiliations

  1. School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Fang Dong, Wan-Chen Pan, Jian-Quan Liu & Xiang-Shan Wang

Authors
  1. Fang Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wan-Chen Pan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jian-Quan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiang-Shan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xiang-Shan Wang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (CIF 20 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dong, F., Pan, WC., Liu, JQ. et al. One-pot synthesis of 2,3-diphenyl-6,7-dihydroimidazo[1,2-f]phenanthridin-8(5H)-ones catalyzed by CuI/l-proline. Monatsh Chem 149, 569–576 (2018). https://doi.org/10.1007/s00706-017-2087-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-017-2087-5

Keywords

Search

Navigation