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
Key words
N ,
N -dimethyl enaminones - C(sp
2 )–H α-functionalization - cyclization reactions - C=C double bond cleavage - heterocycles
