Dually activated organo- and nano-cocatalyzed synthesis of coumarin derivatives

Synthetic Communications

Volumn 39, Issue 13, 2009, Pages 2271-2278

  Goswami, Papori ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Co catalyst; Coumarins; Dual activation; Pechmann reaction; Phenols

Indexed keywords

ACETIC ACID DERIVATIVE; ACETONITRILE; COUMARIN DERIVATIVE; ETHYLACETOACETATE; ETHYLBENZOYLACETATE; PHENOL DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDINE DICARBOXYLIC ACID; UNCLASSIFIED DRUG; ZINC OXIDE;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 67650287650     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802654708     Document Type: Article

References (42)

1. (a) Ma, J.; Cahard, D. Towards perfect catalytic asymmetric synthesis: Dual activation of the electrophile and the nucleophile. Angew. Chem., Int. Ed. 2004, 43, 4566;
2. (b) Gryko, D.; Zimnicka, M.; Lipinski, R. Brønsted acids as additives for the direct asymmetric aldol reaction catalyzed by L-prolinethioamides: Direct evidence for enamine-iminium catalysis. J. Org. Chem. 2007, 72, 964.
3. Yamamoto, H.; Futasugi, K. "Designer acids": Combined acid catalysis for asymmetric synthesis. Angew. Chem., Int. Ed. 2005, 44, 1924.
4. (a) Dalko, P. I.; Moisan, L. In the golden age of organocatalysis. Angew. Chem., Int. Ed. 2004, 43, 5138;
5. (b) Ding, Q.; Wu, J. Lewis acid and organocatalyst- cocatalysed multicomponent reactions of 2-alkynylbenzaldehydes, amines, and ketones. Org. Lett. 2007, 24, 4959;
6. (c) Dalko, P. I.; Moisan, L. Enantioselective organocatalysis. Angew. Chem., Int. Ed. 2001, 40, 3726;
7. (d) Ibrahem, I.; Cordova, A. Direct catalytic intermolecular a-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis. Angew. Chem., Int. Ed. 2006, 45, 1952.
8. Murray, R. D. H. Coumarins. Nat. Prod. Rep. 1995, 12, 477.
9. Zahradnik, M. The production and application of fluorescent brightening agents; John Wiley & Sons, Chichester, UK, 1992.
10. Kennedy, R. O.; Thornes, R. D. Coumarins: Biology, applications, and mode of action; John Wiley & Sons: Chichester, 1997.
11. Cravotto, G.; Nano, G. M.; Palmisano, G.; Tagliapietra, S. An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition. Tetrahedron: Asymmetry 2001, 12, 707.
12. Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry; John Wiley & Sons: New York, 1982.
13. 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.
14. Hassan, V.; Abbas, S.; Gholipur, H. Microwave-assisted synthesis of coumarins via potassium carbonate catalyzed Knoevenagel condensation in 1-n-butyl- 3-methylimidazolium bromide ionic liquid. J. Heterocycl. Chem. 2007, 44, 867.
15. 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.
16. Yavari, I.; Hekmat-shoar, R.; Zonuzi, A. A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt. Tetrahedron Lett. 1998, 39, 2391.
17. Cartwright, G. A.; McNab, H. Synthesis of coumarins by flash vacuum pyrolysis of 3-(2-hydroxyaryl)propenoic esters. J. Chem. Res., Synop. 1997, 296.
18. Sethna, S. M.; Shah, N. M.; Shah, R. C. Aluminium chloride, a new reagent for the condensation of beta-ketonic esters with phenols, part 1: The condensations of methyl β-resorcylate, β-resorcylic acid, and resacetophenone with ethyl acetoacetate. J. Chem. Soc. 1938, 228.
19. Robertson, A.; Sandrock, W. F.; Henry, C. B. Hydroxy-carbonyl compounds, part V: The preparation of coumarins and 1:4-pyrones from phenol, p-cresol, quinol, and α-naphthol. J. Chem. Soc. 1931, 2426.
20. (a) Woods, L. L.; Sapp, J. A new one-step synthesis of substituted coumarins. J. Org. Chem. 1962, 27, 3703-3705;
21. (b) Bulut, M.; Erk, C. Improved synthesis of some hydroxycoumarins. Dyes Pigment 1996, 30, 99.
22. 4-catalyzed one-pot solvent-free protocol for the synthesis of 4-substituted coumarins. Tetrahedron Lett. 2005, 46, 6119;
23. 4 as catalyst under solvent-free conditions. Tetrahedron Lett. 2005, 46, 3501;
24. (c) 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.
25. Wang, L.; Xia, J.; Tian, H.; Qian, C.; Ma, Y. Synthesis of coumarin by Yb(OTf)3-catalyzed Pechmann reaction under the solvent-free conditions. Ind. J. Chem. 2003, 42B, 2097.
26. (a) Potdar, M. R.; Rasalkar, M. S.; Mohile, S. S.; Salunkhe, M. M. Convenient and efficient protocols for coumarin synthesis via Pechmann condensation in neutral ionic liquids. J. Mol. Catal. A: Chem. 2005, 235, 249;
27. 4] ionic liquid: An acid catalyst for improved synthesis of coumarins. Catal. Commun. 2005, 6, 57;
28. (c) Gu, Y.; Zhang, J.; Duan, Z.; Deng, Y. Pechmann reaction in non-chloroaluminate acidic ionic liquids under solvent-free conditions. Adv. Synth. Catal. 2005, 347, 512.
29. (a) Rodriguez-Dominguez, J. C.; Kirsch, G. Sulfated zirconia, a mild alternative to mineral acids in the synthesis of hydroxycoumarins. Tetrahedron Lett. 2006, 47, 3279;
30. (b) Selvakumar, S.; Chidambaram, M.; Singh, A. P. Benzylsulfonic acid functionalized mesoporous Zr-TMS catalysts: An efficient and recyclable catalyst for the preparation of coumarin derivatives by Pechmann condensation reaction. Catal. Commun. 2007, 8, 777;
31. 2 solid acid catalyst for solventfree synthesis of coumarins. J. Mol. Catal. A: Chem. 2006, 256, 290.
32. Maheswara, M.; Siddaiah, V.; Damu, G. L. V.; Rao, Y. K.; Rao, C. V. A solvent-free synthesis of coumarins via Pechmann condensation using heterogeneous catalyst. J. Mol. Catal. A: Chem. 2006, 255, 49.
33. 110] as a green and reusable catalyst. Catal. Commun. 2007, 8, 1886.
34. (a) de la Hoz, A.; Moreno, A.; azquez, E. Use of microwave irradiation and solid acid catalysts in an enhanced and environmentally friendly synthesis of coumarin derivatives. Synlett 1999, 608;
35. 10: Application to the preparation of 4-substituted 7-aminocoumarins. Tetrahedron Lett. 2001, 42, 2791.
36. (a) Goswami, P.; Ali, S.; Khan, M. M.; Khan, A. T. Selective and effective oxone-catalysed a-iodination of ketones and 1,3-dicarbonyl compounds in the solid state. Arkivoc 2007, 15, 82;
37. 3: An efficient and effective solid acid catalyst for transesterification of b-keto esters under solvent-free condition. Catal. Lett. 2008, 124, 100;
38. (c) Goswami, P. One-pot synthesis of unsymmetrical dihydropyridines by green, catalyst free and environmentally benign protocol. Green Chem. Lett. Rev. 2008, 1, 173;
39. (d) Goswami, P.; Ali, S.; Khan, M. M.; Das, B. Metal-free one-pot approach towards the synthesis of Hantzsch esters and their application as the hydrogen source for the reduction of activated olefins catalysed by bromo dimethyl sulfonium bromide (BDMS). Lett. Org. Chem. 2008, 5, 659.
40. Bahekar, S. S.; Shinde, D. B. Samarium(III)-catalyzed one-pot construction of coumarins. Tetrahedron Lett. 2004, 45, 7999.
41. Hegedus, A.; Hell, Z. Zeolite-catalyzed Pechmann synthesis of coumarins. Catal. Lett. 2006, 112, 105.
42. Oyamada, J.; Kitamura, T. Synthesis of coumarins by Pt-catalyzed hydroarylation of propiolic acids with phenols. Tetrahedron 2006, 62, 6918.