Synthesis of Diindolylmethanes (DIMs)
925
As shown in the Table 2, the method presented here represented an efficient procedure in
terms of high yield, mild reaction conditions, and easy workup. For example,
3-((1H-Indol-3-yl)(2-nitrophenyl)methyl)-1H-indole (3f) was previously prepared in 84%
yield catalyzed by ZnO with stirring at 80oC for 45 min9a, whereas present procedure offered
3f in 98% yield at r.t. within 1 min.
In the present procedure, the reaction was very tolerant of aromatic aldehydes carrying
either electron-withdrawing or electron-donating substituent groups. However, the
condensation of indole and ketones (Entries 12~15) or aliphatic aldehydes (Entries 16, 17)
was carried out in lower yields. This indicates that the method has some limitations with
respect to ketones or aliphatic aldehydes.
Conclusion
In summary, we have developed an efficient, environment friendly route to the synthesis of
diindolylmethanes via the condensation of indole with aromatic aldehydes catalyzed with
silicotungstic acid by grinding. But the method has some limitations with respect to ketones
or aliphatic aldehydes.
Acknowledgments
We thank Natural Science Foundation of Hebei Province (B2006000969), China, for
financial support.
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