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DOI: 10.1055/s-0040-1707328
Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones
We are grateful for the financial support from the National Natural Science Foundation of China (21961018), the Natural Science Foundation of Yunnan Province (201901T070302), the Analytical & Testing Foundation of Kunming University of Science and Technology (2017T20130137), and the Fundamental Research Funds for Gannan Medical University (QD202001)
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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(sp2)–H α-functionalization - cyclization reactions - C=C double bond cleavage - heterocyclesPublication History
Received: 20 August 2020
Accepted after revision: 10 September 2020
Article published online:
03 November 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
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