β-Chlorovinyl Ketones to (Thio)chromenones: A Substrate-Controlled Mechanistic Dichotomy

Kyungsoo Oh describes the synthesis of (thio)chromenones via in situ generated β-chlorovinyl ketones.

Chromenones and thiochromenones are widely represented among natural products and their synthetic derivatives typically display a wide array of biological activities. The growing interest in the pharmaceutical properties of (thio)chromenones has spurred the development of novel synthetic methods to (thio)chromenone derivatives. The typical synthetic approaches to chromenones rely on the intramolecular condensation of o-hydroxy 1,3-diones and the intermolecular conjugate addition of o-hydroxy chalcones under oxidation conditions.

In contrast, the synthetic approaches to (thio)chromenones are limited to a handful of Ni-catalyzed and Pd-catalyzed reactions of thio-substituted substrates. With the aim of developing a facile and efficient synthesis of (thio)chromenones without using elaborated substrates or expensive reagents, the group of Professor Kyungsoo Oh at Chung-Ang University (Seoul, South Korea) proposed a reaction sequence of Friedel–Crafts acylation of alkynes and intramolecular cyclization of in situ generated β-chlorovinyl ketones.

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