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HClO4–SiO2-catalyzed synthesis of 12-aryl-12H-benzo[i][1,3]dioxolo[4,5-b]xanthene-6,11-diones and 10-aryl-6,7,8,10-tetrahydro-7,7-dimethyl-9H-[1,3]dioxolo[4,5-b]xanthen-9-ones

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Abstract

Three-component one-pot synthesis of some novel 12-aryl-12H-benzo[i][1,3]dioxolo[4,5-b]xanthene-6,11-diones involving treatment of 3,4-methylenedioxyphenol, aldehydes, and 2-hydroxy-1,4-naphthoquinone in presence of HClO4–SiO2 was achieved, and this reaction was extended to preparation of 10-aryl-6,7,8,10-tetrahydro-7,7-dimethyl-9H-[1,3]dioxolo[4,5-b]xanthen-9-ones by three-component reaction of 3,4-methylenedioxyphenol, aldehydes, and dimedone.

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References

  1. Ito H, Onoue S, Yoshida T (2001) Chem Pharm Bull 49:1229

    Article  CAS  Google Scholar 

  2. Jin L, Chen HS, Jin YS, Liang S, Xiang ZB, Lu J (2008) J Asian Nat Prod Res 10:89

    Article  CAS  Google Scholar 

  3. Hideu T (1981) Jpn Kokai Tokkyo Koho 56005480. Chem Abstr 95:80922b

  4. Lamberk RW, Martin JA, Merrett JH, Parkes KEB, Thomas GJ (1997) PCT Int Appl WO9706178. Chem Abstr 126:212377y

  5. Poupelin JP, Saint-Rut G, Fussard-Blanpin O, Narcisse G, Uchida-Ernouf, Lakroix GR (1978) Eur J Med Chem 13:67

  6. Knight DW, Little PB (2001) J Chem Soc Perkin Trans I 1771

  7. Jha A, Beal J (2004) Tetrahedron Lett 45:8999

    Article  CAS  Google Scholar 

  8. Bekaert A, Andrieux J, Plat M (1992) Tetrahedron Lett 33:2805

    Article  CAS  Google Scholar 

  9. Ohishi T, Kojima T, Matsuoka T, Shiro M, Kotsuko H (2001) Tetrahedron Lett 42:2493

    Article  CAS  Google Scholar 

  10. Papini P, Cimmarusti R (1947) Gazz Chim Ital 77:142

    CAS  Google Scholar 

  11. Ota K, Kito T (1975) Bull Chem Soc Jpn 48:1167

    Google Scholar 

  12. Sen RN, Sarkar N (1925) J Am Chem Soc 47:1079

    Article  CAS  Google Scholar 

  13. Das B, Laxminarayana K, Krishnaiah M, Srinivas Y (2007) Synlett 3107

  14. Misra AK, Tiwari P, Agnihotri G (2005) Synthesis 260

  15. Agnihotri G, Misra AK (2007) Tetrahedron Lett 48:7553

    Article  CAS  Google Scholar 

  16. Tiwari P, Misra AK (2007) Tetrahedron Lett 48:7422

    Article  CAS  Google Scholar 

  17. Bigdeli MA, Heravi MM, Mahdavinia GH (2007) J Mol Catal A: Chem 275:25

    Article  CAS  Google Scholar 

  18. Khan AT, Ghosh S, Choudhury LH (2006) Eur J Org Chem 9:2226

    Article  CAS  Google Scholar 

  19. Wu LQ, Yang CG, Zhang C, Yang LM (2009) Lett Org Chem 6:234

    Article  CAS  Google Scholar 

  20. Heravi MM, Alinejhad H, Bakhtiari K, Oskooie HA (2010) Mol Divers (in press)

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Acknowledgments

We are pleased to acknowledge the financial support from Xinxiang Medical University.

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Correspondence to Liqiang Wu.

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Wu, L., Wu, Y., Yan, F. et al. HClO4–SiO2-catalyzed synthesis of 12-aryl-12H-benzo[i][1,3]dioxolo[4,5-b]xanthene-6,11-diones and 10-aryl-6,7,8,10-tetrahydro-7,7-dimethyl-9H-[1,3]dioxolo[4,5-b]xanthen-9-ones. Monatsh Chem 141, 871–875 (2010). https://doi.org/10.1007/s00706-010-0333-1

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  • DOI: https://doi.org/10.1007/s00706-010-0333-1

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