Skip to main content
SpringerLink
Log in

Facile solvent-free one-pot synthesis of pyranobenzopyrans and their derivatives

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

The condensation of hydroxyl coumarins in a facile one-pot procedure with active methylene esters to afford novel benzopyrans under solventless conditions is described. The products underwent further condensation and cyclization reactions to form novel heterocycles.

A simple and efficient method for synthesis of pyranobenzopyrans has been developed. Further condensation and cyclization of the products into novel heterocycles has also been demonstrated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Cravotta G, Nano G M, Palmisano G and Tagliapietra S 2003 Synthesis 1286

  2. Stahmann A, Ikawa M and Link K P 1948 Chem. Abstr. 42 P603H

    Google Scholar 

  3. Emmanuel-Giota A A, Fylaktakidou K C, Hadjipavlou-Litina D J, Litinas K E and Nicolaides D N 2001 J. Het. Chem. 38 717

    Article  CAS  Google Scholar 

  4. Kontogiorgis C and Litina H D 2003 J. Enzym. Med. 18 63

    Article  CAS  Google Scholar 

  5. Marcu M G, Schulte W T and Neckers L 2000 J. Natl. Cancer Inst. 92 242

    Article  CAS  Google Scholar 

  6. Nofal Z M, El-Zahar M I and Abd El-Karim S S 2000 Molecules 5 99

    Article  CAS  Google Scholar 

  7. Raev L, Voinov E, Ivanov I and Popov D 1990 Pharmazie 45 696

    CAS  Google Scholar 

  8. Tripathi A K, Mukherjee D, Koul S and Taneja S C 2009 ARKIVOC 8 241

    Google Scholar 

  9. Yoon Y, Kim Y O, Lim N Y, Leon W Y and Sung H J 1999 Planta Medica 65 532

    Article  CAS  Google Scholar 

  10. Kerr J F R, Wyllie H A and Currie A R 1972 Br. J. Cancer 26 239

    Article  CAS  Google Scholar 

  11. Dini L 2005 Tissue Cell 37 379

    Article  CAS  Google Scholar 

  12. Rello S, Stockert J C, Moreno V, Gamez A, Pacheco M, Juarranz A, Canete M and Villanueva A 2005 Apoptosis 10 201

    Article  CAS  Google Scholar 

  13. Talapatra S K, Das P K, Chakrabarti R, Mukhopadhyay P K and Talapatra B 1984 Heterocycles 18 519

    Article  Google Scholar 

  14. Talapatra B, Mandal S K, Biswas K, Chakrabarti R and Talapatra S K 2001 Indian J. Chem. Soc. 78 765

    CAS  Google Scholar 

  15. Yoshio I, Masatashi M, Noboru H, Tatsuya M, Yoichi K and Toshiyuki M 2001 Synth. Commun. 31 439

    Article  Google Scholar 

  16. Arora R B and Mathur C N 1963 Brit. J. Pharmacol. Chemother. 20 29

    CAS  Google Scholar 

  17. Balbi A, Sottofattori E, Grandi T, Mazzei M, Abramova T V, Lokhov S G and Lebedev A V 1994 Tetrahedron 50 4009

    Article  CAS  Google Scholar 

  18. Xie L, Takeuchi Y, Mark C L and Lee K 1999 J. Med. Chem. 42 2662

    Article  CAS  Google Scholar 

  19. Reet G V and Heeres J 1979 U. S. Pat. 4160 838

    Google Scholar 

  20. Burch H A and Smith W O 1966 J. Med. Chem. 9 405

    Article  CAS  Google Scholar 

  21. Mir I, Siddique M T and Comric A 1970 Tetrahedron 26 5235

    Article  CAS  Google Scholar 

  22. Hu Z Q, Yang Y X, Shang Y Q, Zhou K and Xu L Z 2006 Acta Cryst. E62 3457

    Google Scholar 

  23. Joule J A and Mills K 2000 Heterocyclic chemistry, 4th edition, Oxford, UK: Blackwell Science

    Google Scholar 

  24. Ohberg L and Wesman J 2001 Synlett. 8 1296

    Article  Google Scholar 

  25. Lipton M F, Basha A, Weinreb S M 1999 Org. Synth. 6 492

    Google Scholar 

  26. Wang W B, Roskamp E J 1992 J. Org. Chem. 57 6101

    Article  CAS  Google Scholar 

  27. Arora R, Paul S, Gupta R 2005 Can J. Chem. 83 1137

    Article  CAS  Google Scholar 

  28. Tietze L F 1996 Chem. Rev. 96 115; (b) Tietze L F, Brasche G, Gericke K M 2006 Domino reactions in organic synthesis, Weinheim: Wiley-VCH

Download references

Author information

Authors and Affiliations

  1. Organic Chemistry Research Laboratory, Ramnarain Ruia College, Matunga, Mumbai 400 019, India

    P SIRISHA, SUHAS PEDNEKAR, ANANT R KAPDI & MINAL NAIK

Authors
  1. P SIRISHA
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. SUHAS PEDNEKAR
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. ANANT R KAPDI
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. MINAL NAIK
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to SUHAS PEDNEKAR.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

(DOC 55 KB)

Rights and permissions

Reprints and permissions

About this article

Cite this article

SIRISHA, P., PEDNEKAR, S., KAPDI, A.R. et al. Facile solvent-free one-pot synthesis of pyranobenzopyrans and their derivatives. J Chem Sci 123, 667–672 (2011). https://doi.org/10.1007/s12039-011-0135-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-011-0135-y

Keywords

Search

Navigation