6316
G. W. Kabalka, A. R. Mereddy / Tetrahedron Letters 46 (2005) 6315–6317
Table 1. Synthesis of flavones and chromones from 1,3-propanedinesa
(10 mL) containing a magnetic stirring bar and a rubber
cap and 3 mL of ethanol. The test tube was placed in the
microwave cavity (CEM, Discover). The tube was sub-
jected to MW at 80 °C (power 100 W) for 5 min. After
completion of the reaction, the tube wasremoved,
cooled to room temperature, and the mixture added to
water. The product wasextracted with methylene chlo-
ride, which was filtered though a short silica column
to afford flavone (98% yield).
Entry Substrate 1
Product 2
Yieldb
(%)
O
O
O
a
98
O
OH
O
O
O
b
c
d
e
97
96
95
96
In conclusion, we report a convenient procedure for
preparing functionalized flavonesand chromonesfrom
1-(2-hydroxyaryl)-3-aryl-1,3-propanedione.
O
O
CH3
OH
CH3
Cl
O
O
Cl
Acknowledgments
CH3
O
O
CH3
OH
O
We wish to thank the US Department of Energy and the
Robert H. Cole foundation for their support of this
research.
O
O
Br
Cl
Br
Cl
O
O
OH
O
References and notes
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O
OH
O
O
O
f
92
89
HO
HO
O
O
HO
HO
OH
O
O
g
OH
O
OH
O
OH
O
O
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h
96
O
O
OH
O
NO2
NO2
O
O
i
j
96
86
CH3
O
O
CH3
OH
O
CF3
O
O
CF3
OH
O
O
Cl
Cl
Br
k
l
95
96
CH3
CH3
O
O
CH3
CH
OH
O
O
Br
O
OH
3
15. (a) Han, C. Cancer Lett. 1997, 114, 153; (b) Birt, D. F.;
Hendrich, S.; Wang, W. Pharmacol. Ther. 2001, 90,
157.
a All productswere identified by 1H, 13C NMR, and comparison with
authentic samples.
b Isolated yields.
16. Banerji, A.; Goomer, N. Synthesis 1980, 874.