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Synthesis 2021; 53(04): 587-610
DOI: 10.1055/s-0040-1707328
DOI: 10.1055/s-0040-1707328
review
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)
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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