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Reusable melamine trisulfonic acid-catalyzed three-component synthesis of 7-alkyl-6H,7H-naphtho[1′,2′:5,6]pyrano[3,2-c]chromen-6-ones

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Abstract

An efficient synthesis of 7-alkyl-6H,7H-naphtho[1′,2′:5,6]pyrano[3,2-c]chromen-6-ones by three-component condensation reaction of β-naphthol, aromatic aldehydes, and 4-hydroxycoumarin under solvent-free conditions in good to excellent yields and short reaction times using reusable melamine trisulfonic acid as solid acid catalyst has been investigated.

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References

  1. Jang KH, Lee BH, Choi BW, Lee H-S, Shin J (2005) J Nat Prod 68:716

    Article  CAS  Google Scholar 

  2. Malquichagua Salazar KJ, Delgado Paredes GE, Lluncor LR, Young MCM, Kato MJ (2005) Phytochemistry 66:573

    Article  CAS  Google Scholar 

  3. Burkhardt G, Becker H, Grubert MTJ, Eicher T (1994) Phytochemistry 37:1593

    Article  CAS  Google Scholar 

  4. Numata A, Kanbara S, Takahashi C, Fujiki R, Yoneda M, Usami Y, Fujita E (1992) Phytochemistry 31:1209

    Article  CAS  Google Scholar 

  5. Kulkarni MM, Nagasampagi BA, Deshpande SG, Sharma RN (1987) Phytochemistry 26:2969

    Article  CAS  Google Scholar 

  6. Isman MB, Proksch P (1985) Phytochemistry 24:1949

    Article  CAS  Google Scholar 

  7. Kitamura ROS, Romoff P, Young MCM, Kato MJ, Lago JHG (2006) Phytochemistry 67:2398

    Article  Google Scholar 

  8. Shanthi G, Perumal PT, Rao U, Sehgal PK (2009) Indian J Chem Sec B 48B:1319

    CAS  Google Scholar 

  9. Foroumadi A, Dehghan G, Samzadeh-Kermani A, Arabsorkhi F, Sorkhi M, Shafiee A, Abdollahi M (2007) Asian J Chem 19:1391

    CAS  Google Scholar 

  10. Kumar D, Reddy VB, Sharad S, Dube U, Kapur S (2009) Eur J Med Chem 44:3805

    Article  CAS  Google Scholar 

  11. El-Saghier AMM, Naili MB, Rammash BK, Saleh NA, Kreddan KM (2007) Arkivoc (xvi):83

  12. Conti C, Desideri N (2009) Bioorg Med Chem 17:3720

    Article  CAS  Google Scholar 

  13. Alizadeh BH, Ostad SN, Foroumadi A, Amini M, Dowlatabadi R, Navidpour L, Shafiee A (2008) Arkivoc (xiii):45

  14. Gourdeau H, Leblond L, Hamelin B, Desputeau C, Dong K, Kianicka I, Custeau D, Boudreau C, Geerts L, Cai S-X, Drewe J, Labrecque D, Kasibhatla S, Tseng B (2004) Mol Cancer Ther 3:1375

    CAS  Google Scholar 

  15. Reddy PN, Reddy YT, Rao MK, Rajitha B (2003) Heterocycl Commun 9:647

    CAS  Google Scholar 

  16. Babu KS, Raju BC, Praveen B, Kishore KH, Murty US, Rao JM (2003) Heterocycl Commun 9:519

    CAS  Google Scholar 

  17. El-Gaby MSA, Zahran MA, Ismail MMF, Ammar YA (2000) Farmaco 55:227

    Article  CAS  Google Scholar 

  18. Cassidy F, Evans JM, Hadley MS, Haladij AH, Leach PE, Stemp G (1992) J Med Chem 35:1623

    Article  CAS  Google Scholar 

  19. Shirini F, Zolfigol MA, Aliakbar A-R, Albadi J (2010) Synth Commun 40:1022

    Article  CAS  Google Scholar 

  20. Shirini F, Albadi J (2010) Bull Korean Chem Soc 31:1119

    Article  CAS  Google Scholar 

  21. Shirini F, Zolfigol MA, Albadi J (2010) Synth Commun 40:910

    Article  CAS  Google Scholar 

  22. Molho D (1961) Bull Soc Chim Fr 1417

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Acknowledgments

We are pleased to acknowledge the financial support by Henan Research Program of Foundation and Advanced Technology (no. 102300410101).

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Authors and Affiliations

  1. School of Pharmacy, Xinxiang Medical University, Xinxiang, 453003, Henan, China

    Weiwei Ma, Xiao Wang, Fulin Yan & Liqiang Wu

  2. School of Basic Medicine, Xinxiang Medical University, Xinxiang, 453003, Henan, China

    Yingling Wang

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  1. Weiwei Ma
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  2. Xiao Wang
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  3. Fulin Yan
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  4. Liqiang Wu
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  5. Yingling Wang
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Correspondence to Liqiang Wu.

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Ma, W., Wang, X., Yan, F. et al. Reusable melamine trisulfonic acid-catalyzed three-component synthesis of 7-alkyl-6H,7H-naphtho[1′,2′:5,6]pyrano[3,2-c]chromen-6-ones. Monatsh Chem 142, 163–167 (2011). https://doi.org/10.1007/s00706-010-0427-9

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  • DOI: https://doi.org/10.1007/s00706-010-0427-9

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