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Facile Synthesis of 9-Acetyl-pyrano[2,3-F]isoflavones
Corresponding Author(s) : Y.V. Rami Reddy
Asian Journal of Chemistry,
Vol. 25 No. 9 (2013): Vol 25 Issue 9
Abstract
The Baylis-Hillman reaction of 7-hydroxy-8-formyl isoflavones (1a-f) react with methyl ketone in presence of l,4-diazobicyclo[2.2.2]octane with nitrogen atmosphere to give 9-acetyl-pyrano[ 2,3-f]isoflavones (3a-f) in good yields.
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- D. Basavaiah, P.D. Rao and R.S. Hyma, Tetrahedron, 52, 8001 (1996).
- S.E. Drewes and G.H.P. Roos, Tetrahedron, 44, 4653 (1988).
- E. Cigank, In ed.: L.A. Paquette, The Morita Baylis-Hillman Reaction, Org. React. John Wiley & Sons, New York, p. 51, 201 (1997).
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- D. Basavaiah, A. Rao, A.K.D.S. Pandiaraju and P.K.S. Sarma, Synlett, 243 (1995); A.B. Baylis and M.E.D. Hillman, German Patent 2155113 (1972); Chem. Abstr., 77, 34174q (l972).
- J. Clayden, G. Nick, W. Stuart and W. Peter, Organic Chemistry, Oxford University Press, London (2001).
- M.L. Bode and P.T. Kaye, J. Chem. Soc. Perkin Trans. I, 1809 (1993).
- M.L. Bode and P.T. Kaye, J. Chem. Soc. Perkin Trans. I, 2612 (1990).
- P. Perlmutter and T.D. Mc Caithy, Aust. J. Chem., 46, 253 (1993).
- S.E. Drewes, O.L. Njamela, N.D. Emslie, N. Ramesar and J.S. Field, Synth. Commun., 23, 2807 (1993).
- M. Hagiwara, S. Inoue, T. Tanaka, K. Nunoki, M. Ito and H. Hidaka, Biochem. Pharmacol., 37, 2987 (1988).
- R.N. Chopra, S.L. Nayar and I.C. Chopra, Glossary of Indian Medicinal Plants, CS1R, New Delhi, p. 241 (1956).
- (a) H. Wagner, L. Frakas, J.B. Harorne, T.J. Mabry and H. Mabry, In: The Flavonolds, Academic Press, New York, p. 127 (1975); (b) J. Gripenberg and T.A. Geissman, The Chemistry of Flavonoid Compounds, Macmillan, New York, p. 409 (1962).
- A.F. Welton, L.D. Tobias, C. Fiedler-Nagy, W. Anderson, W. Hope, K. Meyers and J.W. Coffey, In eds.: V. Cody, E. Middleton Jr., J.B. Harbone and A.R. Liss, In Plant Flavonoids in Biology and Medicine, Inc, New York, p. 231 (1986).
- J.W.T. Selway, Antiviral Activity of Flavones and Flavans, In eds.: E. Middleton and J.B. Harborne, Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure Activity Relationships, New York, p. 521 (1986).
References
D. Basavaiah, P.D. Rao and R.S. Hyma, Tetrahedron, 52, 8001 (1996).
S.E. Drewes and G.H.P. Roos, Tetrahedron, 44, 4653 (1988).
E. Cigank, In ed.: L.A. Paquette, The Morita Baylis-Hillman Reaction, Org. React. John Wiley & Sons, New York, p. 51, 201 (1997).
P. Langer, Angew. Chem. Int. Ed., 39, 3049 (2000).
D. Basavaiah, A. Rao, A.K.D.S. Pandiaraju and P.K.S. Sarma, Synlett, 243 (1995); A.B. Baylis and M.E.D. Hillman, German Patent 2155113 (1972); Chem. Abstr., 77, 34174q (l972).
J. Clayden, G. Nick, W. Stuart and W. Peter, Organic Chemistry, Oxford University Press, London (2001).
M.L. Bode and P.T. Kaye, J. Chem. Soc. Perkin Trans. I, 1809 (1993).
M.L. Bode and P.T. Kaye, J. Chem. Soc. Perkin Trans. I, 2612 (1990).
P. Perlmutter and T.D. Mc Caithy, Aust. J. Chem., 46, 253 (1993).
S.E. Drewes, O.L. Njamela, N.D. Emslie, N. Ramesar and J.S. Field, Synth. Commun., 23, 2807 (1993).
M. Hagiwara, S. Inoue, T. Tanaka, K. Nunoki, M. Ito and H. Hidaka, Biochem. Pharmacol., 37, 2987 (1988).
R.N. Chopra, S.L. Nayar and I.C. Chopra, Glossary of Indian Medicinal Plants, CS1R, New Delhi, p. 241 (1956).
(a) H. Wagner, L. Frakas, J.B. Harorne, T.J. Mabry and H. Mabry, In: The Flavonolds, Academic Press, New York, p. 127 (1975); (b) J. Gripenberg and T.A. Geissman, The Chemistry of Flavonoid Compounds, Macmillan, New York, p. 409 (1962).
A.F. Welton, L.D. Tobias, C. Fiedler-Nagy, W. Anderson, W. Hope, K. Meyers and J.W. Coffey, In eds.: V. Cody, E. Middleton Jr., J.B. Harbone and A.R. Liss, In Plant Flavonoids in Biology and Medicine, Inc, New York, p. 231 (1986).
J.W.T. Selway, Antiviral Activity of Flavones and Flavans, In eds.: E. Middleton and J.B. Harborne, Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure Activity Relationships, New York, p. 521 (1986).