Chalcones, characterized by their α,β-unsaturated carbonyl system conjugated with two aryl rings, represent a versatile and synthetically accessible class of compounds with significant relevance in organic and medicinal chemistry. This chapter explores the multifaceted reactivity of chalcones, emphasizing their role as key intermediates in the synthesis of more complex structures. Four major transformations are discussed in detail: (1) conjugate addition reactions with carbon- and heteroatom-based nucleophiles, (2) Diels–Alder cycloadditions, (3) epoxidation and oxidative cyclization processes, and (4) electrophilic halogenation of the enone system. Mechanistic insights and representative examples highlight how these transformations enable the rapid construction of diverse bioactive scaffolds, including heterocycles and functionalized ketones. The chapter highlights the importance of chalcones as a versatile platform for the development of novel compounds with potential pharmaceutical applications, showcasing their use in modern synthetic strategies.
Chalcones as Versatile Intermediates in Organic Chemistry in "Chalcones From Drug Discovery to Pharmaceutical Applications" / Francesca Clemente, Antonella Capperucci, Damiano Tanini. - STAMPA. - (2026), pp. 93-144. [10.1016/c2024-0-04124-0]
Chalcones as Versatile Intermediates in Organic Chemistry in "Chalcones From Drug Discovery to Pharmaceutical Applications"
Francesca Clemente;Antonella Capperucci;Damiano Tanini
2026
Abstract
Chalcones, characterized by their α,β-unsaturated carbonyl system conjugated with two aryl rings, represent a versatile and synthetically accessible class of compounds with significant relevance in organic and medicinal chemistry. This chapter explores the multifaceted reactivity of chalcones, emphasizing their role as key intermediates in the synthesis of more complex structures. Four major transformations are discussed in detail: (1) conjugate addition reactions with carbon- and heteroatom-based nucleophiles, (2) Diels–Alder cycloadditions, (3) epoxidation and oxidative cyclization processes, and (4) electrophilic halogenation of the enone system. Mechanistic insights and representative examples highlight how these transformations enable the rapid construction of diverse bioactive scaffolds, including heterocycles and functionalized ketones. The chapter highlights the importance of chalcones as a versatile platform for the development of novel compounds with potential pharmaceutical applications, showcasing their use in modern synthetic strategies.| File | Dimensione | Formato | |
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