Abstract
Stannic(IV) chloride has been demonstrated to be an efficient catalyst for the Pechmann condensation of phenols and β-ketoesters to produce structurally diverse coumarins in a solvent-free protocol. The practical and simple method led to excellent yields of the coumarin derivatives under mild conditions and within short times.
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References
R.O. Kennedy, R.D. Tharnes: Coumarins: Biology, Application and Mode of Action; Wiley and Sons, Chichester 1997.
R.D.H. Murray, J. Mendez, S.A. Brown: The Natural Coumarins: Occurrence, Chemistry and Biochemistry; Wiley and Sons: New York 1982.
L.A. Singer, N.P. Kong: J. Am. Chem. Soc., 88, 5213 (1966).
M. Zahradnik: The Production and Application of Fluorescent Brightening Agents; Wiley and Sons, 1992.
G. Cravotto, G.M. Nano, G. Palmisano, S. Tagliapietra: Tetrahedron Asymmetry, 12, 707 (2001).
G.-J. Fan, W. Mar, M.K. Park, E. Wook Choi, K. Kim, S. Kim: Bioorg. Med. Chem. Lett., 11, 2361 (2001).
F. Bigi, L. Chesini, R. Maggi, G. Sartori: J. Org. Chem., 64, 1033 (1999).
I. Yavari, R. Hekmat-Shoar, A. Zonuzi: Tetrahedron Lett., 39, 2391 (1998).
B.J. Donnelly, D.M.X. Donnelly, A.M. O’sullivan: Tetrahedron, 24, 2617 (1968).
A.M. Varughese, R.P. Bhat, S.D. Samant: Tetrahedron Lett., 46, 6957 (2005)
G.P. Romanelli, D. Bennardi, D.M. Ruiz, G. Baronetti, H.J. Thomas, J.C. Autino: Tetrahedron Lett., 45, 8935 (2004)
L.L. Woods, J.A. Sapp: J. Org. Chem., 27, 3703 (1962)
H. Valizadeh, A. Shockravi: Tetrahedron Lett., 46, 3501 (2005)
M.K Potdar, S.S. Mohile, M.M. Salunkhe: Tetrahedron Lett., 42, 9285 (2001)
D. Subhas Bose, A.P. Rudradas, M. Hari Babu: Tetrahedron Lett., 43, 9195 (2002).
S. Frére, V. Thiéry, T. Besson: Tetrahedron Lett., 42, 2791 (2001)
A.J. Hoefnagel, E.A. Geenewagh, R.S. Downing, H.V. Bekkum: J. Chem. Soc., Chem. Commun., 225 (1995)
S.S. Bahekar, D.B. Shinde: Tetrahedron Lett., 45, 7999 (2004)
P.R. Singh, D.U. Singh, S.D. Samant: Synlett, 11, 1909 (2004).
M.S. Manhas, S.N. Ganguly, S. Mukherjee, A.K. Jain, A.K. Bose: Tetrahedron Lett., 47, 2423 (2006).
B.G. Mishra, D. Kumar, V.S. Rao: Catal. Commun., 7, 457 (2006)
D. Kumar, M.S. Swapna, B.G. Mishra: Chemistry Lett., 35, 1074 (2006).
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Naik, M.A., Mishra, B.G. & Dubey, A. A simple and efficient protocol for the synthesis of substituted comarins catalyzed by stannic(IV) chloride under solvent-free condition. React Kinet Catal Lett 91, 169–175 (2007). https://doi.org/10.1007/s11144-007-5128-y
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DOI: https://doi.org/10.1007/s11144-007-5128-y