Expeditious Pechmann condensation by using biodegradable cellulose sulfuric acid as a solid acid catalyst

Synthetic Communications

Volumn 40, Issue 22, 2010, Pages 3358-3364

  Kuarm, B Suresh ^a   Madhav, J Venu ^a   Laxmi, S Vijaya ^a   Rajitha, B ^a   Reddy, Y Thirupathi ^b   Reddy, P Narsimha ^b   Crooks, Peter A ^b  

^a NATIONAL INSTITUTE OF TECHNOLOGY   (India)

^b University of Kentucky   (United States)

Author keywords

Cellulose sulfuric acid; coumarins; Pechmann condensation; solvent free conditions

Indexed keywords

CELLULOSE; COUMARIN DERIVATIVE; PHENOL DERIVATIVE; SULFURIC ACID;

ARTICLE; CATALYST; MICROWAVE IRRADIATION; POLYMERIZATION; REACTION TIME; SYNTHESIS;

EID: 77958025850     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903419860     Document Type: Article

References (30)

1. O'Kennedy, R.; Thornes, R. D. Coumarins: Biology, Applications, and Mode of Action; John Wiley and Sons: Chichester, 1997.
2. Murray, R. D.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry; John Wiley & Sons: New York, 1982.
3. 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.
4. Kayser, O.; Kolodziej, H. Antibacterial activity of extracts and constituents of Pelargonium sidoides and Pelargonium reniforme. Planta Med. 1997, 63, 508.
5. 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.
6. Fan, G. J.; Mar, W.; Park, M. K.; Wook Choi, E.; Kim, K.; Kim, S. A novel class of inhibitors for steroid 5a-reductase: Synthesis and evaluation of umbelliferone derivatives. Bioorg. Med. Chem. Lett. 2001, 11, 2361.
7. 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.
8. Sethna, S. M.; Phadke, R. The Pechmann reaction. Org. React. 1953, 7, 1.
9. 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.
10. Jones, G. Knoevenagel condensation. Org. React. 1967, 15, 204
11. 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.
12. Yavari, I.; Hekmat-Shoar, R.; Zonuzi, A. A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt. Tetrahedron Lett. 1998, 39, 2391.
13. Nadkarni, A. J.; Kudav, N. A. Convenient synthesis of 8-methoxy-4-methyl-coumarin. Ind. J. Chem. 1981, 20B, 719-720.
14. 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.
15. 4-catalyzed Pechmann reaction: Synthesis of coumarins under solvent-free conditions. Synth. Commun. 2004, 34, 3997.
16. 3-catalyzed Pechmann reaction under the solvent-free conditions. Ind. J. Chem. 2003, 42B, 2097.
17. Woods, L. L.; Sapp, J. A new one-step synthesis of substituted coumarins. J. Org. Chem. 1962, 27, 3703.
18. 0-methylpsoralen derivatives. Photochem. Photobiol. 1993, 58, 486-491.
19. Khaikin, M. S.; Petrova, N. L.; Kukhtin, V. A. Chlorination of dihydroxy coumarins. Zh. Obshch. Khim. 1963, 33, 3941.
20. Sugino, T.; Tanaka, K. Solvent-free coumarin synthesis. Chem. Lett. 2001, 2, 110.
21. Sachin, B. P.; Ramakrishna, P. B.; Vivek, P. R.; Shriniwas, D. S. Ultrasound-assisted pechmann condensation of phenols with b-ketoesters to form coumarins, in the presence of bismuth(III) chloride catalyst. Synth. Commun. 2006, 36, 525.
22. 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.
23. Sushilkumar, S. B.; Devanand, B. S. Samarium(III)-catalyzed one-pot construction of coumarins. Tetrahedron Lett. 2004, 45, 7999.
24. 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.
25. Amit, K. C.; Bhushan, K. M. Pechmann reaction in chloroaluminate ionic liquid. Synlett 2002, 152.
26. Ahmad, S.; Ali, M. Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot three-component synthesis of a-amino nitriles. Appl. Catal. A: Gen. 2007, 331, 149.
27. Ahmad, S.; Ali, M.; Jafar, M. R.; Ebrahim, S. Cellulose sulfuric acid catalyzed one-pot three-component synthesis of imidazoazines. Chem. Pharm. Bull. 2007, 55, 957.
28. Ahmad, S.; Abbas, R.; Zahra, B. Sulfonated cellulose and starch: New biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines. Catal. Commun. 2008, 9, 13.
29. Venu Madhav, J.; Thirupathi Reddy, Y.; Narsimha Reddy, P.; Nikhil Reddy, M.; Suresh, K.; Crooks, P. A.; Rajitha, B. Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo [a.j] xanthenes under solvent-free conditions. J. Mol. Catal. A 2009, 304, 85-87.
30. Narsimha Reddy, P.; Thirupathi Reddy, Y.; Nikhil Reddy, M.; Rajitha, B.; Crooks, P. A. Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)- ones. Synth. Commun. 2009, 39, 1257.