EXPEDITIOUS PECHMANN CONDENSATION
3363
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. (a) Jones, G. Knoevenagel condensation. Org. React. 1967, 15, 204; (b) 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.
11. Yavari, I.; Hekmat-Shoar, R.; Zonuzi, A.
A new and efficient route to 4-
carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt. Tetrahedron
Lett. 1998, 39, 2391.
12. Nadkarni, A. J.; Kudav, N. A. Convenient synthesis of 8-methoxy-4-methyl-coumarin.
Ind. J. Chem. 1981, 20B, 719–720.
13. 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.
14. Smitha, G.; Reddy, C. S. ZrCl4-catalyzed Pechmann reaction: Synthesis of coumarins
under solvent-free conditions. Synth. Commun. 2004, 34, 3997.
15. 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.
16. Woods, L. L.; Sapp, J. A new one-step synthesis of substituted coumarins. J. Org. Chem.
1962, 27, 3703.
17. Zagotto, G.; Gia, O.; Baccichetti, F.; Uriarte, E.; Palumbo, M. Synthesis and photobio-
logical properties of 4-hydroxymethyl-40-methylpsoralen derivatives. Photochem.
Photobiol. 1993, 58, 486–491.
18. Khaikin, M. S.; Petrova, N. L.; Kukhtin, V. A. Chlorination of dihydroxy coumarins. Zh.
Obshch. Khim. 1963, 33, 3941.
19. Sugino, T.; Tanaka, K. Solvent-free coumarin synthesis. Chem. Lett. 2001, 2, 110.
20. 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.
21. 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.
22. Sushilkumar, S. B.; Devanand, B. S. Samarium(III)-catalyzed one-pot construction of
coumarins. Tetrahedron Lett. 2004, 45, 7999.
23. 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.
24. Amit, K. C.; Bhushan, K. M. Pechmann reaction in chloroaluminate ionic liquid. Synlett
2002, 152.
25. 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.