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Heterogeneous catalytic three-component one-pot synthesis of novel 8H-[1,3]dioxolo[4,5-g]chromenes by basic alumina in water

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Abstract

The three-component one-pot synthesis of 6-amino-8-aryl-7-cyano-8H-[1,3]dioxolo[4,5-g]chromene systems, via condensation of 3,4-(methylenedioxy)phenol, aldehydes, and malononitrile using a catalytic amount of basic alumina in refluxing water is reported.

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References

  1. Bocian W, Kawechi R, Bednarek E, Sitkowski J, Ulkowska A, Kozerski L (2006) New J Chem 30:467

    Article  CAS  Google Scholar 

  2. Mitscher LA (2005) Chem Rev 105:559

    Article  CAS  Google Scholar 

  3. Cassady JM, Baird WM, Chang C (1990) J Nat Prod 53:23

    Article  CAS  Google Scholar 

  4. Morris J, Wishka DG, Lin AH, Humphrey WR, Wiltse AL, Gammil RB, Judge TM, Bisaha SL, Olds NL, Jacob CS, Bergh CL, Cudahy MM, Williams DJ, Nishizawa EE, Thomas EW, Gorman RR, Benjamin CW, Shebuski RJ (1993) J Med Chem 36:2026

    Article  CAS  Google Scholar 

  5. Graham JG, Zhang H, Pendland SL, Santalsiero BD, Mesecar AD, Cabieres F, Farnsworth NR (2004) J Nat Prod 67:225

    Article  CAS  Google Scholar 

  6. Ishar MPS, Singh G, Singh S, Sreenivasan KK, Singh G (2006) Bioorg Med Chem Lett 16:1366

    Article  CAS  Google Scholar 

  7. Burgard A, Lang H-J, Gerlach U (1999) Tetrahedron 55:7555

    Article  CAS  Google Scholar 

  8. Evans JM, Fake CS, Hamilton TC, Poyser RH, Showell GA (1984) J Med Chem 27:1127

    Article  CAS  Google Scholar 

  9. Evans JM, Fake CS, Hamilton TC, Poyser RH, Watts EA (1983) J Med Chem 26:1582

    Article  CAS  Google Scholar 

  10. Arnesto D, Horspool WM, Martin N, Ramos A, Seaone C (1989) J Org Chem 54:3069

    Article  Google Scholar 

  11. Hatakeyama S, Ochi N, Numata H, Takano SA (1988) J Chem Soc Chem Commun 17:1202

    Google Scholar 

  12. Callaghan CN, Marry TBH (1995) J Chem Res (S) 57(7):214

    Google Scholar 

  13. Ballini R, Bosica G, Conforti ML, Maggi R, Mazzacani A, Righi P, Sartori G (2001) Tetrahedron 57:1395

    Article  CAS  Google Scholar 

  14. Tajbakhsh M, Mohajerani B, Heravi MM, Ahmadi AN (2005) J Mol Catal A Chem 236:216

    Article  CAS  Google Scholar 

  15. Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) J Mol Catal A Chem 276:226

    Article  CAS  Google Scholar 

  16. Heravi MM, Vazin M, Faghihi Z (2013) Green Chem Lett Rev 6:282

    Article  CAS  Google Scholar 

  17. Heravi MM, Jani BA, Derikvan FN, Bamoharram FF, Oskoiee AH (2008) Catal Commun 10:272

    Article  CAS  Google Scholar 

  18. Heravi MM, Zadsirjan V, Bakhtiari Kh, Oskooie HA, Bamoharram FF (2007) Catal Commun 8:315

    Article  CAS  Google Scholar 

  19. Komiyama T, Takaguchi Y, Tsuboi S (2004) Tetrahedron Lett 45:6299

    Article  CAS  Google Scholar 

  20. Evans DA, Tedrow JS, Shaw JT, Downey W (2002) J Am Chem Soc 124:392

    Article  CAS  Google Scholar 

  21. Van Bekkum H, Flanigen EM, Jansen JC (1991) Stud Surf Sci Catal 58:xiii

    Article  Google Scholar 

  22. Balogh M, Laszlo P (1993) Organic chemistry using clays. Springer, Berlin

    Google Scholar 

  23. Smith K (1992) Solids supports and catalysts in organic synthesis. Ellis Horwood, Chichester

    Google Scholar 

  24. Paul S, Nanda P, Gupta R (2003) Molecules 8:374

    Article  CAS  Google Scholar 

  25. Reddy BM, Patil MK (2008) Curr Org Chem 12:118

    Article  CAS  Google Scholar 

  26. Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) Catal Commun 8:289

    Article  CAS  Google Scholar 

  27. Heravi MM, Derikvand F, Ranjbar L, Oskooie HA, Bamoharram FF (2007) J Mol Catal A Chem 261:156

    Article  CAS  Google Scholar 

  28. Heravi MM, Derikvand F, Bamoharram FF (2007) J Mol Catal A Chem 263:112

    Article  CAS  Google Scholar 

  29. Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) Catal Commun 8:289

    Article  CAS  Google Scholar 

  30. Heravi MM, Alimadadi Jani B, Derikvand F, Bamoharram FF, Oskooie HA (2008) Catal Commun 10:272

    Article  CAS  Google Scholar 

  31. Heravi MM, Baghernejad B, Oskooie HA, Hekmatshoar R (2008) Tetrahedron Lett 49:6101

    Article  CAS  Google Scholar 

  32. Heravi MM, Behbahani FK, Daraie M, Oskooie HA (2009) Mol Divers 13:375

    Article  CAS  Google Scholar 

  33. Heravi MM, Moghimi S (2012) Tetrahedron Lett 53:392

    Article  CAS  Google Scholar 

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Acknowledgments

MMH thanks the Iran National Science Foundation for the partial financial support.

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Authors and Affiliations

  1. Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran

    Majid M. Heravi & Mansoureh Daraie

Authors
  1. Majid M. Heravi
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  2. Mansoureh Daraie
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Correspondence to Majid M. Heravi.

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Heravi, M.M., Daraie, M. Heterogeneous catalytic three-component one-pot synthesis of novel 8H-[1,3]dioxolo[4,5-g]chromenes by basic alumina in water. Monatsh Chem 145, 1479–1482 (2014). https://doi.org/10.1007/s00706-014-1201-1

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  • DOI: https://doi.org/10.1007/s00706-014-1201-1

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