Potassium Phosphate Catalyzed a Rapid Three-Component Synthesis of Tetrahydrobenzo[b]pyran at Ambient Temperature

Abstract

An efficient, rapid, one-pot synthesis of tetrahydrobenzo[b]pyran is achieved via a three-component reaction of aldehydes, 1,3-diketone, malononitrile in 20% ethanol using anhydrous potassium phosphate as a catalyst at room temperature. The key advantages are the short reaction time, high yields, simple work-up, inexpensive catalyst and purification of products by non-chromatographic methods, i.e. by simple recrystallization from ethanol.

Graphical Abstract

An efficient, rapid, one-pot synthesis of tetrahydrobenzo[b]pyran is achieved via a three-component reaction of aldehydes, dimedone, malononitrile in 20% ethanol using anhydrous potassium phosphate as a catalyst at room temperature. The key advantages are the short reaction time, high yields, simple work-up, inexpensive catalyst and purification of products by non-chromatographic methods, i.e. by simple recrystallization from ethanol.

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References

  1. 1.

    Foye WO (1991) Prinicipi di Chemico Farmaceutica Piccin. Padova, Italy, p 416

    Google Scholar 

  2. 2.

    Andreani LL, Lapi E (1960) Bull Chim Farm 99:583

    Google Scholar 

  3. 3.

    Zhang YL, Chen BZ, Zheng KQ, Xu ML, Lei XH, Yao Xue Xue Bao (1982) 17:17 Chem Abstr 96(1982)135383e

  4. 4.

    Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med Chem 28:517

    Article  CAS  Google Scholar 

  5. 5.

    Witte EC, Neubert P, Roesch A (1986) Ger Offen DE, 3427985 Chem Abstr 104(1986) 224915f

  6. 6.

    Konkoy CS, Fick DB, Cai SX, Lan NC, Keana JFW, PCT Int Appl WO 0075123, (2000); Chem Abstr 134(2001)29313a

  7. 7.

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

    Article  Google Scholar 

  8. 8.

    Hatakeyama S, Ochi N, Numata H, Takano S (1988) J Chem Soc Chem Commun 21:1202

    Article  Google Scholar 

  9. 9.

    Gonzalez R, Martin N, Seoane C, Soto J (1985) J Chem Soc, Perkin Trans.1 1202

  10. 10.

    Martin N, Martin G, Seoane AC, Maco JL, Albert A, Cano FH (1993) Ann Chem 7:801

    Google Scholar 

  11. 11.

    Maco JL, Martin N, Grau AM, Seoane C, Albert A, Cano FH (1994) Tetrahedron 50(11):3509

    Article  Google Scholar 

  12. 12.

    Hassanien AA, Zahrran MA, El-Gaby MSA, Ghorab MM (1999) J Indian Chem Soc 76:350

    CAS  Google Scholar 

  13. 13.

    Svarez M, Salfran E, Verdecia Y, Ochoa E, Alba L, Martin N, Martinez R, Quinteiro M, Seoane A, Novoa H, Blaton N, Peeters OM, Ranter CD (2002) Tetrahedron 58:953

    Article  Google Scholar 

  14. 14.

    Bandgar SB, Bandgar BP, Korbad BL, Totre JV, Patil S (2007) Aust J Chem 60(4):305

    Article  CAS  Google Scholar 

  15. 15.

    Saini A, Kumar S, Sandhu JS (2006) Synlett 5:1928

    Google Scholar 

  16. 16.

    Bhosale RS, Magar CV, Solanke KS, Mane SB, Choudhary SS, Pawar RP (2007) Synth Commun 37:4353

    Article  CAS  Google Scholar 

  17. 17.

    Seifi M, Sheibani H (2008) Catal Lett 126:275

    Article  CAS  Google Scholar 

  18. 18.

    Wang LM, Shao JH, Tian H, Wang YH, Liu B (2006) J Fluorine Chem 127:97

    Article  CAS  Google Scholar 

  19. 19.

    Balalie S, Bararjanian M, Sheikh-Ahmadi M, Hekmat S, Salehi P (2007) Synth Commun 37:1097

    Article  Google Scholar 

  20. 20.

    Tu S-J, Gao Y, Guo C, Shi D, Lu Z (2002) Synth Commun 32:2137

    Article  CAS  Google Scholar 

  21. 21.

    El-Rahaman NMA, El-Kateb AA, Mady MF (2007) Synth Commun 37(22):3961

    Article  Google Scholar 

  22. 22.

    Tu SJ, Jiang H, Zhuang QY, Miao CB, Shi DQ, Wang XS, Gao Y (2003) Chin J Org Chem 23:488

    CAS  Google Scholar 

  23. 23.

    Li JT, Xu WZ, Yang LC, Li TS (2004) Synth Commun 34:4565

    Article  CAS  Google Scholar 

  24. 24.

    Fotouhi L, Heravi MM, Fatehi A, Bakhtiari K (2007) Tetrahedron Lett 48:5379

    Article  CAS  Google Scholar 

  25. 25.

    Lian X-Z, Huang Y, Li Y-Q, Zheng W-J (2008) Monatshefte fur Chemie 139:129

    Article  CAS  Google Scholar 

  26. 26.

    Balalaie S, Bararjanian M, Amani AM, Movassagh B (2006) Synlett 2:263

    Article  Google Scholar 

  27. 27.

    Guo S-B, Wang S-X, Li J-T (2007) Synth Commun 37:2111

    Article  CAS  Google Scholar 

  28. 28.

    Desai UV, Pore DM, Mane RB, Solabannavar SB, Wadgaonkar PP (2004) Synth Commun 34:25

    Article  CAS  Google Scholar 

  29. 29.

    Desai UV, Pore DM, Mane RB, Solabannavar SB, Wadgaonkar PP (2004) Synth Commun 34:19

    Article  CAS  Google Scholar 

  30. 30.

    Pore DM, Soudagar MS, Desai UV, Thopate TS, Wadagaonkar PP (2006) Tetrahedron Lett 47:9325

    Article  CAS  Google Scholar 

  31. 31.

    Joshi AV, Bhusare S, Baidossi M, Qafisheh N, Sasson Y (2005) Tetrahedron Lett 46:3583

    Article  CAS  Google Scholar 

  32. 32.

    Li RT, Ding PY, Han M, Cai MS (1998) Synth Commun 28:295

    Article  CAS  Google Scholar 

  33. 33.

    Lin S-W, Sun Q, Li R-T, Cheng T-M, Ge Z-M (2007) Synthesis 13:1933

    Google Scholar 

  34. 34.

    Urawa Y, Ogura K (2003) Tetrahedron Lett 44:271

    Article  CAS  Google Scholar 

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Acknowledgments

Authors DMP and KAU thank UGC, New Delhi for financial assistance [F.2-3/2007(Policy/SR)] and for the Research Fellowship, respectively.

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Correspondence to D. M. Pore.

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Pore, D.M., Undale, K.A., Dongare, B.B. et al. Potassium Phosphate Catalyzed a Rapid Three-Component Synthesis of Tetrahydrobenzo[b]pyran at Ambient Temperature. Catal Lett 132, 104–108 (2009). https://doi.org/10.1007/s10562-009-0074-0

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Keywords

  • Three-component
  • Tetrahydrobenzo[b]pyran
  • Potassium phosphate
  • One-pot synthesis