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Tandem synthesis of benzo[d]naphtho[2,3-g][1,3]oxazocine-8,13(6H,14H)-dione derivatives

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Abstract

An efficient and facile method for the synthesis of novel naphthooxazocines from 2-hydroxy-1,4-naphthoquinone and quinolinium salts at room temperature is described. The reaction proceeds through C-alkylation and intramolecular O-alkylation, affording the desired products in good yields.

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References

  1. Shigemori H, Kagata T, Ishiyama H, Morah F, Ohsaki A, Kobayashi J (2003) Chem Pharm Bull 51:58

    Article  CAS  Google Scholar 

  2. Zhang CR, Liu HB, Dong SH, Zhu JY, Wu Y, Yue JM (2009) Org Lett 11:4692

    Article  CAS  Google Scholar 

  3. Lounasmaa M, Karvinen E (1993) Heterocycles 36:751

    Article  CAS  Google Scholar 

  4. Klohs MW, Draper MS, Petracek FJ, Ginzel KH, Re ON (1972) Arzneim-Forsch (Drug Res) 22:132

    CAS  Google Scholar 

  5. Mishra JK, Samanta K, Jain M, Dikshit M, Panda G (2010) Biorgan Med Chem Lett 20:244

    Article  CAS  Google Scholar 

  6. Seto S, Tanioka A, Ikeda M, Izawa S (2005) Biorgan Med Chem Lett 15:1485

    Article  CAS  Google Scholar 

  7. Sahn JJ, Martin SF (2011) Tetrahedron Lett 52:6855

    Article  CAS  Google Scholar 

  8. Narjes F, Crescenzi B, Ferrara M, Habermann J, Colarusso S, del Rosario MRF, Stansfield I, Mackay AC, Conte I, Ercolani C, Zaramella S, Palumbi MC, Meuleman P, Leroux-Roels G, Giuliano C, Fiore F, Di Marco S, Baiocco P, Koch U, Migliaccio G, Altamura S, Laufer R, De Francesco R, Rowley M (2011) J Med Chem 54:289

    Article  CAS  Google Scholar 

  9. Broggini G, Bruch L, Garanti L, Zecchi G (1994) J Chem Soc Perkin Trans 1:433

    Article  Google Scholar 

  10. Gurubrahamam R, Nagarajua K, Chen K (2018) Chem Commun 54:6048

    Article  CAS  Google Scholar 

  11. Sivaguru P, Parameswaran K, Lalitha A (2016) Tetrahedron Lett 57:2549

    Article  CAS  Google Scholar 

  12. Zhang E, Zhang X, Wei W, Wang D, Cai Y, Xu T, Yana M, Yong Z (2015) RSC Adv 5:5288

    Article  CAS  Google Scholar 

  13. Van Otterlo WAL, Morgans GL, Khanye SD, Aderibigbe BAA, Michael JP, Billing DG (2004) Tetrahedron Lett 45:9171

    Article  Google Scholar 

  14. Klapars A, Parris S, Anderson KW, Buchwald SL (2004) J Am Chem Soc 126:3529

    Article  CAS  Google Scholar 

  15. Mishra JK, Panda G (2007) J Comb Chem 9:321

    Article  CAS  Google Scholar 

  16. Yang T, Lin C, Fu H, Jiang Y, Zhao Y (2005) Org Lett 7:4781

    Article  CAS  Google Scholar 

  17. Tietze LF, Gordon B, Kersten GM (2006) Domino reactions in organic synthesis. Wiley, Weinheim

    Book  Google Scholar 

  18. Hayashi Y (2016) Chem Sci 7:866

    Article  CAS  Google Scholar 

  19. Guo HC, Ma JA (2006) Angew Chem Int Ed 45:354

    Article  CAS  Google Scholar 

  20. Hussian MM, Walsh PJ (2008) Acc Chem Res 41:883

    Article  Google Scholar 

  21. Moghaddam FM, Mirjafary Z, Saeidian H, Taheri S, Doulabi M, Kiamehr M (2010) Tetrahedron 66:134

    Article  CAS  Google Scholar 

  22. Moghaddam FM, Taheri S, Mirjafary Z, Saeidian H (2010) Synlett 1:123

    Article  Google Scholar 

  23. Moghaddam FM, Saeidian H, Kiamehr M, Mirjafary Z, Taheri S (2010) Arkivoc 11:91

    Google Scholar 

  24. Schmidt A, Michalik D, Rotzoll S, Ullah E, Fischer C, Reinke H, Görls H, Langer P (2008) Org Biomol Chem 6:2804

    Article  CAS  Google Scholar 

  25. Bazin M, Kuhn C (2005) J Comb Chem 7:302

    Article  CAS  Google Scholar 

  26. Nájera C, Sansano JM, Yus M (2015) Org Biomol Chem 13:8596

    Article  Google Scholar 

  27. Liu Y, Zhang Y, Shen YM, Hu HW, Xu JH (2010) Org Biomol Chem 8:2449

    Article  CAS  Google Scholar 

  28. Wu L, Sun J, Yan CG (2012) Org Biomol Chem 10:9452

    Article  CAS  Google Scholar 

  29. Zhao J, Li P, Wu C, Chen H, Ai W, Sun R, Ren H, Larock RC, Shi F (2012) Org Biomol Chem 10:1922

    Article  CAS  Google Scholar 

  30. Noushini S, Mahdavi M, Firoozpour L, Moghimi S, Shafiee A, Foroumadi A (2015) Tetrahedron 71:6272

    Article  CAS  Google Scholar 

  31. Firoozpour L, Nikookar H, Moghimi S, Mahdavi M, Asadipour A, Ranjbar PR, Foroumadi A (2017) Heterocycl Commun 23:305

    Article  CAS  Google Scholar 

  32. Sadat-Ebrahimi SE, Katebi S, Pirali-Hamedani M, Moghimi S, Yahya-Meymandi A, Mahdavi M, Shafiee A, Foroumadi A (2016) Heterocycl Commun 22:247

    Article  CAS  Google Scholar 

  33. Yahyavi H, Heravi MM, Mahdavi M, Foroumadi A (2018) Tetrahedron Lett 59:94

    Article  CAS  Google Scholar 

  34. Yahya-Meymandi A, Nikookar H, Moghimi S, Mahdavi M, Firoozpour L, Asadipour A, Ranjbar PR, Foroumadi A (2017) J Iran Chem Soc 14:771

    Article  CAS  Google Scholar 

  35. Almasirad A, Firoozpour L, Nejati M, Edraki N, Firuzi O, Khoshneviszadeh M, Mahdavi M, Moghimi S, Safavi M, Shafiee A, Foroumadi A (2016) Z Naturforsch B 71:205

    Article  CAS  Google Scholar 

  36. Rezaei Z, Moghimi S, Javaheri R, Asadi M, Mahdavi M, Shabani S, Edraki N, Firuzi O, Safavi M, Amini M, Asadipour A, Zeinalzadeh E, Firoozpour L, Foroumadi A (2017) Lett Drug Des Discov 14:1138

    Article  CAS  Google Scholar 

  37. Loska R, Majcher M, Makosza M (2007) J Org Chem 72:5574

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported and funded by a grant from the research council of Tehran University of Medical Sciences (TUMS).

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Authors and Affiliations

  1. Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran

    Fatemeh Madani Qamsari & Shahram Moradi

  2. Drug Design and Development Research Center, The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran

    Alireza Foroumadi

  3. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

    Mohammad Mahdavi

  4. Department of Chemistry, Imam Hossein University, Tehran, Iran

    Abolghasem Moghimi

Authors
  1. Fatemeh Madani Qamsari
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  2. Shahram Moradi
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  3. Alireza Foroumadi
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  4. Mohammad Mahdavi
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  5. Abolghasem Moghimi
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Corresponding author

Correspondence to Alireza Foroumadi.

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Madani Qamsari, F., Moradi, S., Foroumadi, A. et al. Tandem synthesis of benzo[d]naphtho[2,3-g][1,3]oxazocine-8,13(6H,14H)-dione derivatives. Monatsh Chem 150, 347–352 (2019). https://doi.org/10.1007/s00706-018-2322-8

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  • DOI: https://doi.org/10.1007/s00706-018-2322-8

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