Xanthan sulfuric acid: An efficient and recyclable solid acid catalyst for Pechmann condensation

Synthetic Communications

Volumn 42, Issue 12, 2012, Pages 1770-1777

  Kuarm, B Suresh ^a   Madhav, J Venu ^a   Rajitha, B ^a  

^a NATIONAL INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Biodegradable xanthan sulfuric acid (XSA); Coumarins; Pechmann condensation; Solvent free conditions

Indexed keywords

ACETOACETIC ACID DERIVATIVE; COUMARIN; PHENOL; SOLVENT; SULFURIC ACID; XANTHAN;

ARTICLE; CATALYST; COST EFFECTIVENESS ANALYSIS; POLYMERIZATION; REACTION TIME; SUBSTITUTION REACTION;

EID: 84857556481     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.543964     Document Type: Article

References (40)

1. Cavettos, G.; Nano, G. M.; Palmisano, G.; Tagliapietra, S. An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition. Tetrahedron: Asymmetry 2001, 12, 707.
2. Kayser, O.; Kolodziej, H. Antibacterial activity of extracts and constituents of Pelargonium sidoides and Pelargonium reniforme. Planta Med. 1997, 63, 508.
3. Wang, C. J.; Hsieh, Y. J.; Chu, C. Y.; Lin, Y. L.; Tseng, T. H. Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin. Cancer Lett. 2002, 183, 163.
4. Fan, G. J.; Mar, W.; Park, M. K.; Wook Choi, E.; Kim, K.; Kim, S. A. Novel class of inhibitors for steroid 5α-reductase: Synthesis and evaluation of umbelliferone derivatives. Bioorg. Med. Chem. Lett. 2001, 11, 2361.
5. Kirkiacharian, S.; Thuy, D. T.; Sicsic, S.; Bakhchinian, R.; Kurkjian, R.; Tonnaire, T. Structure-activity relationships of some 3-substituted-4- hydroxycoumarins as HIV-1 protease inhibitors. Farmaco. 2002, 57, 703.
6. Singer, L. A.; Kong, N. P. Vinyl radicals: Stereoselectivity in hydrogen atom transfer to equilibrated isomeric vinyl radicals. J. Am. Chem. Soc. 1966, 88, 5213.
7. Kennedy, O.; Thornes, R. D. Coumarins: Biology, Applications, and Mode of Action; Wiley: Chichester, 1997.
8. Zahradnik, M. The Production and Application of Fluorescent Brightening Agents; Wiley: Chichester, 1990.
9. Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry and Biochemistry; Wiley: New York, 1982.
10. (a) Sethna, S. M.; Phadke, R. The pechmann reaction. Org. React. 1953, 7, 1;
11. (b) Donnelly, B. J.; Donnelly, D. M. X.; Sullivan, A. M. O. Dalbergia species-VI: The occurrence of melannein in the genus Dalbergia. Tetrahedron 1968, 24, 2617;
12. (c) Jones, G. Knoevenagel condensation. Org. React. 1967, 15, 204;
13. (d) Bigi, F.; Chesini, L.; Maggi, R.; Sartori, G. Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids. J. Org. Chem. 1999, 64, 1033.
14. Yavari, I.; Hekmat-shoar, R.; Zonuzi, A. A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt. Tetrahedron Lett. 1998, 39, 2391.
15. Sethna, S.; Phadke, R. The Pechmann reaction. Org. React. 1953, 7, 1.
16. Russell, A.; Frye, J. R. 2,4-Dihydroxyacetophenone. Org. Synth. 1941, 21, 22.
17. Nadkarni, A. J.; Kudav, N. A. Convenient synthesis of 8-methoxy-4-methyl-coumarin. Ind. J. Chem. 1981, 20B, 719-720.
18. Bose, D. S.; Rudradas, A. P.; Babu, M. H. The indium(III) chloride-catalyzed von Pechmann reaction: A simple and effective procedure for the synthesis of 4-substituted coumarins. Tetrahedron Lett. 2002, 43, 9195.
19. 4-catalyzed pechmann reaction: synthesis of coumarins under solvent-free conditions. Synth. Commun. 2004, 34, 3997.
20. 3 catalyzed Pechmann reaction under the solvent-free conditions. Ind. J. Chem. 2003, 42B, 2097.
21. Sugino, T.; Tanaka, K. Solvent-free coumarin synthesis. Chem. Lett. 2001, 2, 110.
22. Sachin, B. P.; Ramakrishna, P. B.; Vivek, P. R.; Shriniwas, D. S. Ultrasound-assisted Pechmann condensation of phenols with β-ketoesters to form coumarins, in the presence of bismuth(III) chloride catalyst. Synth. Commun. 2006, 36, 525.
23. Jie, W.; Tianning, D.; Wei, S.; Yizhe, L. Expeditious approach to coumarins via Pechmann reaction catalyzed by molecular iodine or AgOTf. Synth. Commun. 2006, 36, 2949.
24. Sushilkumar, S. B.; Devanand, B. S. Samarium(III)-catalyzed one-pot construction of coumarins. Tetrahedron Lett. 2004, 45, 7999.
25. Mahesh, P. K.; Swapnil, M. S.; Manikrao, S. M. Coumarin syntheses via pechmann condensation in lewis acidic chloroaluminate ionic liquid. Tetrahedron Lett. 2001, 42, 9285-9287.
26. Amit, K. C.; Bhushan, K. M. Pechmann reaction in chloroaluminate ionic liquid. Synlett 2002, 152.
27. Breslow, R. Biomimetic control of chemical selectivity. Acc. Chem. Res. 1980, 13, 170.
28. Clark, J. H.; Macquarrie, D. J. Green Chemistry and Technology; Blackwell: Abingdon, 2002.
29. Huang, K.; Xue, L.; Hu, Y. C.; Huang, M.-Y.; Jiang, Y. Y. Catalytic behaviors of silicasupported starch-polysulfosiloxane-Pt complexes in asymmetric hydrogenation of 4-methyl-2-pentanone. React. Funct. Polym. 2002, 50, 199.
30. Shaabani, A.; Maleki, A.; Soudi, M. R.; Mofakham, H. Xanthan sulfuric acid: A new and efficient bio-supported solid acid catalyst for the synthesis of α-amino nitriles by condensation of carbonyl compounds, amines, and trimethylsilylcyanide. Catal. Commun. 2009, 10, 945.
31. (a) Venu Madhav, J.; Suresh Kuarm, B.; Someshwar, P.; Rajitha, B.; Thirupathi Reddy, Y.; Crooks, P. A. Dipyridine cobalt chloride: A novel and efficient catalyst for the synthesis of coumarins via Pechmann condensation under conventional method and microwave irradiation. J. Chem. Res. 2008, 4, 232-234;
32. (b) Rajitha, B.; Naveen Kumar, V.; Venu Madhav, J.; Someshwar, P. Dipyridine copper chloride-catalyzed coumarin synthesis via Pechmann condensation under conventional heating and microwave irradiation. Arkivoc 2006, 12, 23-27 (Pubitemid 44005311)
33. (c) Thirupathi Reddy, Y.; Vijayakumar, N. S.; Crooks, P. A.; Pavan, K. D.; Narsimha Reddy, P.; Rajitha, B. Ceric ammonium nitrate (CAN): An efficient catalyst for the coumarin synthesis via Pechmann condensation using conventional heating and microwave irradiation. Synth. Commun. 2008, 38, 2082-2088; (Pubitemid 351948431)
34. (d) Sunil Kumar, B.; Thirupathi Reddy, Y.; Narsimha Reddy, P.; Kumar, P. S.; Rajitha, B. Selectfluor: A simple and efficient catalyst for the synthesis of substituted coumarins under solvent-free conditions. J. Heterocycl. Chem. 2006, 43(2), 477-479.
35. Kumar, S.; Anil, S.; Sandhu, J. S. LiBr-mediated, solvent-free von Pechmann reaction: Facile and efficient method for the synthesis of 2H-chromen-2-ones. Arkivoc 2007, 15, 18.
36. Woods, L. L.; Sapp, J. A new one-step synthesis of substituted coumarins. J. Org. Chem. 1962, 27, 3703.
37. 3-catalyzed Pechmann reaction under the solvent-free conditions. Ind. J. Chem. 2003, 42B, 2097.
38. (a) Khaikin, M. S.; Petrova, N. L.; Kukhtin, V. A. Synthesis of coumarins. Zh. Obshch. Khim. 1963, 33, 3941-3943;
39. (b) Sugino, T.; Tanaka, K. Solvent-free coumarin synthesis. Chem. Lett. 2001, 4, 110.
40. Maheswara, M.; Siddaiah, V.; Guri, L. V. D.; Rao, Y. K.; Rao, C. V. A solvent-free synthesis of coumarins via Pechmann condensation using heterogeneous catalyst. J. Mol. Catal. A 2006, 255, 49-52. (Pubitemid 44067534)