Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Abstract

Abstract Enaminones are gaining increasing interest because of their unique properties and their importance in organic synthesis as versatile building blocks. N,N-Dimethyl enaminones offer a better leaving group (a dimethylamine group) than other enaminones, and allow further elaboration via a range of facile chemical transformations. Over the past five years, there have been an increasing number of reports describing the synthetic applications of N,N-dimethyl enaminones. This review provides a comprehensive overview on the synthetic applications of N,N-dimethyl enaminones that have been reported since 2016. 1 Introduction 2 Direct C(sp2)–H α-Functionalization 2.1 Synthesis of α-Sulfenylated N,N-Dimethyl Enaminones 2.2 Synthesis of α-Thiocyanated N,N-Dimethyl Enaminones 2.3 Synthesis of α-Acyloxylated N,N-Dimethyl Enaminones 3 Functionalization Reactions via C=C Double Bond Cleavage 3.1 Synthesis of Functionalized Methyl Ketones 3.2 Synthesis of α-Ketoamides, α-Ketoesters and 1,2-Diketones 3.3 Synthesis of N-Sulfonyl Amidines 4 Construction of All-Carbon Aromatic Scaffolds 4.1 Synthesis of Benzaldehydes 4.2 Synthesis of the Naphthalenes 5 Construction of Heterocyclic Scaffolds 5.1 Synthesis of Five-Membered Heterocycles 5.2 Synthesis of Six-Membered Heterocycles 5.3 Synthesis of Quinolines 5.4 Synthesis of Functionalized Chromones 5.5 Synthesis of Other Fused Polycyclic Heterocycles 6 Conclusions and Perspectives