在碱和双氧水存在下,2’-羟基查尔酮(2’-hydroxychalcones)氧化环化转化为 2-芳基-3-羟基-4H-1苯并吡喃-4-酮(黄酮醇,flavonols)的反应。此反应也发生副反应生成橙酮(aurone)类化合物。
反应机理
先进行亲核环氧化,接着进行分子内的β-亲核进攻关环,接着迅速氧化得到产物。
如果进行分子内α-亲核进攻,则生成橙酮类化合物。
反应实例
【J. Heterocycl. Chem. 1968, 5, 425-426.】
相关文献
1. Algar, J.; Flynn, J. P. Proc. Roy. Irish Acad. 1934, B42, 1-8. Algar and Flynn were Irish chemists.
2. Oyamada, T. J. Chem. Soc. Jpn 1934, 55, 1256-1261.
3. Oyamada, T. Bull. Chem. Soc. Jpn. 1935, 10, 182-186.
4. Wheeler, T. S. Record Chem. Progr. 1957, 18, 133-161. (Review).
5. Smith, M. A.; Neumann, R. M.; Webb, R. A. J. Heterocycl. Chem. 1968, 5, 425-426.
6. Wagner, H.; Farkas, L. In The Flavonoids; Harborne, J. B.; Mabry, T. J.; Mabry H.,Eds.; Academic Press: New York, 1975, 1, pp 127-213. (Review).
7. Wollenweber, E. In The Flavonoids: Advances in Research; Harborne, J. B.; Mabry,T. J., Eds; Chapman and Hall: New York, 1982, pp 189-259. (Review).
8. Wollenweber, E. In The Flavonoids: Advances in Research since 1986; Harborne, J. B., Ed.; Chapman and Hall: New York, 1994, pp 259-335. (Review).
10. Bohm, B. A.; Stuessy, T. F. Flavonoids of the Sunflower Family (Asteraceae); Springer-Verlag: New York, 2000. (Review).
11. Limberakis, C. Algar-Flynn-Oyamada Reaction. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 496-503. (Review).
编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Algar-Flynn-Oyamada Reaction,page 6-7.
相关反应
Allan–Robinson反应
Auwers黄酮合成反应 返回搜狐,查看更多
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