Synthesis and reactivity of 3-(1-alkynyl)chromones

Abstract

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.