上海
在碱性条件下邻羟基芳基酮和脂肪酸酐反应制备色酮和香豆素类化合物的反应。此反应由Kostanecki和Rozycki在1901年首先报道，利用邻羟基芳基酮和脂肪酸酐在相应的脂肪酸钠盐存在下，通过O-酰基化和 Aldol缩合得到 色酮和香豆素类化合物。由于此反应和类似，因此反应也被称为Kostanecki-Robinson反应。 反应机理和 类似。主要是以芳香甲酸酐为底物，反应得到的是黄酮和异黄酮类化合物。
反应机理
香豆素类
色酮类
反应实例
【 J. Indian Chem. Soc. 1972 , 49, 599-604】
【 J. Med. Chem. 1996 , 39, 1303-1313】
【Bioorg. Med. Chem. Lett. 2008,16, 4064–4074】
A mixture of 4.0 g aromatic compound, 4.0 g potassium propanate, and 6.6 mL propanicanhydride was refluxed at 135◦C for 2 h and then cooled down. The mixture was poured into water. The brown solid was filtered and crystallized from dimethylformamide to give 22% coumarin-product.
【J. Org. Chem., 1968, 33, 1746】
相关文献
1. von Kostanecki, S.; Rozycki, A. Ber. 1901, 34, 102-109.
2. Pardanani, N. H.; Trivedi, K. N. J. Indian Chem. Soc. 1972, 49, 599-604.
3. Flavin, M. T.; Rizzo, J. D.; Khilevich, A.; et al. J. Med. Chem. 1996, 39, 1303-1313.
4. Mamedov, V. A.; et al. Chemistry of Heterocyclic Compounds 2003, 39, 96-100.
5. Limberakis, C. KostaneckiRobinson Reaction. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 521-535. (Review).
6. Hwang, I.-T.; Lee, S.-A.; Hwang, J.-S.; Lee, K.-I. Mol. 2011, 16, 6313-6321.
编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Kostanecki reaction，page 353.
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