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Synthesis and reactivity of 3-(1-alkynyl)chromones
Russian Chemical Reviews ( IF 7.7 ) Pub Date : 2021-04-14 , DOI: 10.1070/rcr5008
Vyacheslav Ya. Sosnovskikh

For the first time, the literature data on the methods of synthesis and reactivity of 3-(1-alkynyl)chromones are summarized and systematized. The main method for obtaining these compounds is the Sonogashira cross-coupling reaction of 3-halochromones with terminal acetylenes, and their most important chemical properties include the transformation into furans, reactions with dinucleophiles, ambiphilic [4+2]- and [4+3]-cyclizations, and also dimerization and mixed condensation of 2-methyl-3-(1-alkynyl)chromones due to the vinylogous methyl group. Except for the oxacyclization to furans, chemical transformations of 3-(1-alkynyl)chromones are accompanied by pyrone ring transformation, in which not only the carbonyl group but also the triple bond can participate. This significantly increases the synthetic value of these compounds and ensures the production of more complex heterocyclic systems based on them. The mechanisms of the reactions are discussed, the conditions for their implementation and the yields of the resulting products are indicated.

The bibliography includes 80 references.



中文翻译:

3-(1-炔基)色酮的合成及反应性

首次对3-(1-炔基)色酮的合成方法和反应性的文献资料进行了总结和系统化。获得这些化合物的主要方法是 3-卤代色酮与末端乙炔的 Sonogashira 交叉偶联反应,它们最重要的化学性质包括转化为呋喃、与双亲核试剂反应、两亲 [4+2]- 和 [4+3 ]-环化,以及由于插枝甲基而导致的 2-甲基-3-(1-炔基)色酮的二聚和混合缩合。3-(1-炔基)色酮的化学转化除了氧杂环化成呋喃外,还伴随着吡喃酮环转化,不仅羰基参与,三键也参与。这显着提高了这些化合物的合成价值,并确保生产基于它们的更复杂的杂环系统。讨论了反应的机理,指出了它们的实施条件和所得产物的产率。

参考书目包括 80 篇参考文献。

更新日期:2021-04-14
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