Table of Contents
ISRN Organic Chemistry
Volume 2013, Article ID 526173, 6 pages
http://dx.doi.org/10.1155/2013/526173
Research Article

DABCO Catalyzed Synthesis of Xanthene Derivatives in Aqueous Media

Laboratory of Heterocycles, School of Studies in Chemistry & Biochemistry, Vikram University, Ujjain, Madhya Pradesh 456010, India

Received 25 January 2013; Accepted 14 February 2013

Academic Editors: V. P. Kukhar, G. Li, J. C. Menéndez, and Z. Wimmer

Copyright © 2013 Pradeep Paliwal 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. R. V. A. Orru and M. De Greef, “Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds,” Synthesis, no. 10, pp. 1471–1499, 2003. View at Google Scholar · View at Scopus
  2. A. Domling, “Recent developments in isocyanide-based multicomponent reactions in applied chemistry,” Chemical Reviews, vol. 106, no. 1, pp. 17–89, 2006. View at Publisher · View at Google Scholar
  3. A. Domling and I. Ugi, “Multicomponent reactions with isocyanides,” Angewandte Chemie International Edition, vol. 39, no. 18, pp. 3168–3210, 2000. View at Publisher · View at Google Scholar
  4. J. Peng, W. Hao, X. Wang, S. Tu, N. Ma, and G. Zhang, “Microwave-assisted synthesis of pyrazolo[4,3-f]quinolin-7-one derivatives via multi-component reactions,” Chinese Journal of Chemistry, vol. 27, no. 9, pp. 1707–1710, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. L. F. Tietze, H. Evers, and E. Töpken, “A novel concept in combinatorial chemistry in solution with the advantages of solid-phase synthesis: formation of N-betaines by multicomponent domino reactions,” Angewandte Chemie International Edition, vol. 40, no. 5, pp. 903–905, 2001. View at Publisher · View at Google Scholar
  6. T. Masquelin, H. Bui, B. Brickley, G. Stephenson, J. Schwerkoske, and C. Hulme, “Sequential Ugi/Strecker reactions via microwave assisted organic synthesis: novel 3-center-4-component and 3-center-5-component multi-component reactions,” Tetrahedron Letters, vol. 47, no. 17, pp. 2989–2991, 2006. View at Publisher · View at Google Scholar · View at Scopus
  7. A. Djandé, M. Kiendrébéogo, M. Compaoré et al., “Antioxidant potential of 4-acyl isochroman-1, 3-diones,” Research Journal of Chemical Sciences, vol. 1, no. 5, pp. 88–90, 2011. View at Google Scholar
  8. S. M. Menchen, S. C. Benson, J. Y. L. Lam et al., Patent, US, 6583168, 2003.
  9. C. G. Knight and T. Stephens, “Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles,” Biochemical Journal, vol. 258, no. 3, pp. 683–689, 1989. View at Google Scholar · View at Scopus
  10. A. K. Bhattacharya and K. C. Rana, “Microwave-assisted synthesis of 14-aryl-14H-dibenzo[a.j]xanthenes catalysed by pTSA in solution and solvent-free conditions,” Mendeleev Communications, vol. 17, no. 4, pp. 247–248, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. G. Mulongo, J. Mbabazi, B. Odongkara, H. Twinomuhwezi, and G. B. Mpango, “New biologically active compounds from 1, 3-diketones,” Research Journal of Chemical Sciences, vol. 1, no. 3, pp. 102–108, 2011. View at Google Scholar
  12. Z. Karimi-Jaberi and M. M. Hashemi, “One step synthesis of 14-alkyl- or aryl-14H-dibenzo[a,j]xanthenes using sodium hydrogen sulfate as catalyst,” Monatshefte fur Chemie, vol. 139, no. 6, pp. 605–608, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. M. Seyyedhamzeh, P. Mirzaei, and A. Bazgir, “Solvent-free synthesis of aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst,” Dyes and Pigments, vol. 76, no. 3, pp. 836–839, 2008. View at Publisher · View at Google Scholar · View at Scopus
  14. J. Q. Wang and R. G. Harvey, “Synthesis of polycyclic xanthenes and furans via palladium-catalyzed cyclization of polycyclic aryltriflate esters,” Tetrahedron, vol. 58, no. 29, pp. 5927–5931, 2002. View at Publisher · View at Google Scholar · View at Scopus
  15. G. Casiraghi, G. Casnati, M. Catellani, and M. A. A. Corina, “Convenient one-step synthesis of xanthene derivatives,” Synthesis, no. 8, pp. 564–564, 1974. View at Google Scholar
  16. S. Gupta, P. Gupta, A. Sachar, and R. L. Sharma, “Synthetic studies of some varied structural systems of biologically potent polynitrogen heteropolycyclics,” Indian Journal of Chemistry B, vol. 49, no. 9, pp. 1243–1256, 2010. View at Google Scholar · View at Scopus
  17. M. H. Majid, A. Hamideh, B. Khadijeh, S. Mina, A. O. Hossein, and F. B. Fatemeh, “Solvent-free synthesis of xanthenes derivatives by preyssler type heteropolyacid,” Bulletin of Chemical Society of Ethiopia, vol. 25, no. 3, pp. 399–406, 2011. View at Google Scholar
  18. K. Muharrem, “Aldol condensation and michael addition of 4, 4-dimethylcyclohexane-1, 3-dione and aromatic aldehydes. Unconventional substituent effects,” Chinese Journal of Chemistry, vol. 29, no. 11, pp. 2355–2360, 2011. View at Publisher · View at Google Scholar
  19. A. Ilangovan, S. Malayappasamy, S. Muralidharan, and S. Maruthamuthu, “A highly efficient green synthesis of 1, 8-dioxooctahydroxanthenes,” Chemistry Central Journal, vol. 5, pp. 81–86, 2011. View at Publisher · View at Google Scholar
  20. B. Baghernejad, “4-Diazabicyclo [2,2,2] octane (DABCO) as a useful catalyst in organic synthesis,” European Journal of Chemistry, vol. 1, no. 1, pp. 54–60, 2010. View at Publisher · View at Google Scholar
  21. H. Yang, R. Tian, and Y. Li, “Organic reactions catalyzed by 1, 4-diazabicyclo [2.2.2] octane (DABCO),” Frontiers of Chemistry in China, vol. 3, no. 3, pp. 279–287, 2008. View at Publisher · View at Google Scholar · View at Scopus
  22. X. Da-Zhen, Y. Liu, S. Shi, and Y. Wang, “A simple, efficient and green procedure for Knoevenagel condensation catalyzed by [C4dabco][BF4] ionic liquid in water,” Green Chemistry, vol. 12, no. 3, pp. 514–517, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. M. Bigdeli, “Clean synthesis of 1,8-dioxooctahydroxanthenes promoted by DABCO-bromine in aqueous media,” Chinese Chemical Letters, vol. 21, no. 10, pp. 1180–1182, 2010. View at Publisher · View at Google Scholar · View at Scopus
  24. B. Saeed, R. Sorour, B. Morteza, and H. G. Jurgen, “DABCO-catalyzed efficient synthesis of naphthopyran derivatives via one-pot three-component condensation reaction at room temperature,” Synthetic Communications, vol. 38, no. 7, pp. 1078–1089, 2008. View at Publisher · View at Google Scholar · View at Scopus
  25. K. Y. Lee, J. M. Kim, and J. N. Kim, “Synthesis of 2,3,4,4a-tetrahydroxanthen-1-ones and 3,3a-dihydro-2H-cyclopenta[b]chromen-1-ones from the reaction of salicylaldehydes and 2-cyclohexen-1-one and 2-cyclopenten-1-one,” Bulletin of the Korean Chemical Society, vol. 24, no. 1, pp. 17–18, 2003. View at Google Scholar · View at Scopus
  26. S. Jain, G. N. Babu, S. R. Jetti, S. Harshada, and D. Suryaprakash, “Synthesis, antitubercular and antifungal activities of heteroaryl -substituted oxirance derived from Baylis-Hillman adducts,” Medicinal Chemistry Research, vol. 21, no. 10, pp. 2744–2748, 2012. View at Publisher · View at Google Scholar
  27. S. Jain, P. Paliwal, and G. N. Babu, “DABCO promoted one-pot synthesis of dihydro pyrano(c) chromene and pyrano[2, 3-d]pyrimidine derivatives and their biological activities,” Journal of Saudi Chemical Society, 2011. View at Publisher · View at Google Scholar