Algar-Flynn-Oyamada氧化重排

在碱和甲醇实际上下，2’-吡啶查尔醛（2’-hydroxychalcones）氧化物加成转化为 2-芳基-3-吡啶-4H-1苯并吡喃-4-醛（黄醛醇，flavonols）的质子化。此质子化也引发副质子化生成蓝醛（aurone）有机酸。

质子化机理

先展开亲核环氧化物，接着展开分子结构内的β-亲核进攻关环，接着很快氧化物得到产物。

如果展开分子结构内α-亲核进攻，则生成蓝醛有机酸。

质子化实例

【 J. Heterocycl. Chem. 1968, 5, 425-426.】

关的典籍

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.

关的质子化

Allan–Robinson质子化

Auwers黄醛人工合成质子化