Table of Contents
Organic Chemistry International
Volume 2012 (2012), Article ID 208948, 4 pages
http://dx.doi.org/10.1155/2012/208948
Research Article

Triton-B-Catalyzed, Efficient, Solvent-Free Synthesis of Benzopyrans

1Laboratory of Medicinal Chemistry, Amity Institute of Pharmacy, Amity University Uttar Pradesh, Lucknow Campus, Lucknow 226010, India
2Synthetic Research Laboratory, Department of Chemistry, B. S. A. College, Mathura 281004, India

Received 5 June 2012; Accepted 16 August 2012

Academic Editor: William N. Setzer

Copyright © 2012 Devdutt Chaturvedi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. M. Curini, G. Cravotto, F. Epifano, and G. Giannone, “Chemistry and biological activity of natural and synthetic prenyloxycoumarins,” Current Medicinal Chemistry, vol. 13, no. 2, pp. 199–222, 2006. View at Publisher · View at Google Scholar · View at Scopus
  2. M. V. Kulkarni, G. M. Kulkarni, C. H. Lin, and C. M. Sun, “Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents,” Current Medicinal Chemistry, vol. 13, no. 23, pp. 2795–2818, 2006. View at Publisher · View at Google Scholar · View at Scopus
  3. T. C. Wang, I. L. Chen, P. J. Lu et al., “Synthesis, antiproliferative, and antiplatelet activities of oxime- and methyloxime-containing flavone and isoflavone derivatives,” Bioorganic and Medicinal Chemistry, vol. 13, no. 21, pp. 6045–6053, 2005. View at Publisher · View at Google Scholar · View at Scopus
  4. N. Kim, S. Lee, K. Y. Yi et al., “Identification of a novel antiangiogenic agent; 4-(N-imidazol-2-ylmethyl)amino benzopyran analogues,” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 10, pp. 1661–1663, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. G. Rastelli, L. Costantino, M. C. Gamberini et al., “Binding of 1-benzopyran-4-one derivatives to aldose reductase: a free energy perturbation study,” Bioorganic and Medicinal Chemistry, vol. 10, no. 5, pp. 1427–1436, 2002. View at Publisher · View at Google Scholar · View at Scopus
  6. L. Tang, J. Yu, Y. Leng, Y. Feng, Y. Yang, and R. Ji, “Synthesis and insulin-sensitizing activity of a novel kind of benzopyran derivative,” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 20, pp. 3437–3440, 2003. View at Publisher · View at Google Scholar · View at Scopus
  7. Y. R. Lee and X. Wang, “A short synthetic route to biologically active (±)-daurichromenic acid as highly potent anti-HIV agent,” Organic and Biomolecular Chemistry, vol. 3, no. 21, pp. 3955–3957, 2005. View at Publisher · View at Google Scholar · View at Scopus
  8. D. J. Hadjipavlou-Litina, K. E. Litinas, and C. Kontogiorgis, “The anti-inflammatory effect of coumarin and its derivatives,” Anti-Inflammatory and Anti-Allergy Agents in Medicinal Chemistry, vol. 6, no. 4, pp. 293–306, 2007. View at Publisher · View at Google Scholar · View at Scopus
  9. H. Göker, D. W. Boykin, and S. Yildiz, “Synthesis and potent antimicrobial activity of some novel 2-phenyl or methyl-4H-1-benzopyran-4-ones carrying amidinobenzimidazoles,” Bioorganic and Medicinal Chemistry, vol. 13, no. 5, pp. 1707–1714, 2005. View at Publisher · View at Google Scholar · View at Scopus
  10. S. Prado, Y. L. Janin, B. Saint-Joanis et al., “Synthesis and antimycobacterial evaluation of benzofurobenzopyran analogues,” Bioorganic and Medicinal Chemistry, vol. 15, no. 5, pp. 2177–2186, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. M. Koufaki, C. Kiziridi, P. Papazafiri et al., “Synthesis and biological evaluation of benzopyran analogues bearing class III antiarrhythmic pharmacophores,” Bioorganic and Medicinal Chemistry, vol. 14, no. 19, pp. 6666–6678, 2006. View at Publisher · View at Google Scholar · View at Scopus
  12. A. Gupta, A. Dwivedy, G. Keshri et al., “Rapid synthesis of 4-benzylidene and 4-[bis-(4-methoxyphenyl)-methylene-2-substituted phenyl-benzopyrans as potential selective estrogen receptor modulators (SERMs) using McMurry coupling reaction,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 23, pp. 6006–6012, 2006. View at Publisher · View at Google Scholar · View at Scopus
  13. F. Karci and N. Ertan, “Synthesis of some novel hetarylazo disperse dyes derived from 4-hydroxy-2H-1-benzopyran-2-one (4-hydroxycoumarin) as coupling component and investigation of their absorption spectra,” Dyes and Pigments, vol. 64, no. 3, pp. 243–249, 2005. View at Publisher · View at Google Scholar · View at Scopus
  14. T. Kakimoto, F. Koizumi, K. Hirase, S. Banba, E. Tanaka, and K. Arai, “Novel 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2] benzopyran derivatives: Synthesis of chiral glycol benzyl ether herbicides,” Pest Management Science, vol. 60, no. 5, pp. 493–500, 2004. View at Publisher · View at Google Scholar · View at Scopus
  15. J. Lloyd, K. S. Atwal, H. J. Finlay et al., “Benzopyran sulfonamides as KV1.5 potassium channel blockers,” Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 12, pp. 3271–3275, 2007. View at Publisher · View at Google Scholar · View at Scopus
  16. A. F. E. Mourad, A. A. Aly, H. H. Farag, and E. A. Beshr, “Microwave assisted synthesis of triazoloquinazolinones and benzimidazoquinazolinones,” Beilstein Journal of Organic Chemistry, vol. 3, p. 11, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. S. S. Joshi and H. Singh, “Nitrohydroxy aromatic ketones. I. Nitrohydroxyacetophenones,” Journal of The American Chemical Society, vol. 76, no. 19, pp. 4993–4994, 1954. View at Google Scholar · View at Scopus
  18. G. L. Zhao, Y. L. Shi, and M. Shi, “Synthesis of functionalized 2H-1-benzopyrans by DBU-catalyzed reactions of salicylic aldehydes with allenic ketones and esters,” Organic Letters, vol. 7, no. 20, pp. 4527–4530, 2005. View at Publisher · View at Google Scholar · View at Scopus
  19. J. L. Portscheller and H. C. Malinakova, “Synthesis of 2H-1-benzopyrans via palladacycles with a metal-bonded stereogenic carbon,” Organic Letters, vol. 4, no. 21, pp. 3679–3681, 2002. View at Publisher · View at Google Scholar · View at Scopus
  20. T. S. Jin, J. C. Xiao, S. J. Wang, T. S. Li, and X. R. Song, “An efficient and convenient approach to the synthesis of benzopyrans by a three-component coupling of one-pot reaction,” Synlett, no. 13, pp. 2001–2004, 2003. View at Google Scholar · View at Scopus
  21. K. Pachamuthu and R. R. Schmidt, “Diels-Alder reaction of 2-nitro glycals: a new route to the synthesis of benzopyrans,” Synlett, no. 9, pp. 1355–1357, 2003. View at Google Scholar · View at Scopus
  22. J. S. Yadav, B. V. S. Reddy, M. Aruna, and M. Thomas, “A facile synthesis of trans-fused pyrano[3,2-c]benzopyrans catalyzed by scandium triflate,” Synthesis, no. 2, pp. 217–220, 2002. View at Google Scholar · View at Scopus
  23. J. Y. Hwang, H. S. Choi, J. S. Seo et al., “Construction of a 2,6-difunctionalized 2-methyl-2H-1-benzopyran library by using a solid-phase synthesis protocol,” Journal of Organic Chemistry, vol. 70, no. 24, pp. 10151–10154, 2005. View at Publisher · View at Google Scholar · View at Scopus
  24. S. A. Galena, “Microwave Chemistry,” Chemical Society Reviews, vol. 26, pp. 233–238, 1997. View at Google Scholar
  25. D. Chaturvedi and S. Ray, “A high yielding, one-pot, triton-B catalyzed, expeditious synthesis of carbamate esters by four component coupling methodology,” Monatshefte fur Chemie, vol. 137, no. 2, pp. 201–206, 2006. View at Publisher · View at Google Scholar · View at Scopus
  26. D. Chaturvedi and S. Ray, “Triton-B catalyzed efficient one-pot synthesis of dithiocarbamate esters,” Monatshefte fur Chemie, vol. 137, no. 3, pp. 311–317, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. D. Chaturvedi and S. Ray, “Triton-B catalyzed, efficient, one-pot synthesis of carbamate esters from alcoholic tosylates,” Monatshefte fur Chemie, vol. 137, no. 4, pp. 459–463, 2006. View at Publisher · View at Google Scholar · View at Scopus
  28. D. Chaturvedi and S. Ray, “A high yielding, one-pot, triton-B catalyzed synthesis of dithiocarbamates using alcoholic tosylates,” Monatshefte fur Chemie, vol. 137, no. 4, pp. 465–469, 2006. View at Publisher · View at Google Scholar · View at Scopus
  29. D. Chaturvedi, A. K. Chaturvedi, N. Mishra, and V. Mishra, “Triton-B-catalyzed, efficient, one-pot synthesis of carbazates through alcoholic tosylates,” Synthetic Communications, vol. 38, no. 22, pp. 4013–4022, 2008. View at Publisher · View at Google Scholar · View at Scopus