Synthesis ( IF 2.6 ) Pub Date : 2020-11-03 , DOI: 10.1055/s-0040-1707328 Fuchao Yu 1 , Jiuzhong Huang 2
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
中文翻译:
基于N,N-二甲基烯胺酮的有机合成的新进展
烯胺酮因其独特的性能及其作为通用构建单元在有机合成中的重要性而日益引起人们的关注。N,N-二甲基烯胺酮提供比其他烯胺酮更好的离去基团(二甲胺基),并允许通过一系列简便的化学转化进行进一步修饰。在过去的五年中,越来越多的报告描述了N,N-二甲基烯胺酮的合成应用。这篇综述提供了自2016年以来已报道的N,N-二甲基烯胺酮的合成应用的全面概述。
1引言
2直接C(sp 2)–Hα-官能化
2.1α-亚磺酰基化的N,N-二甲基烯胺酮的合成
2.2α-硫氰酸化N,N-二甲基烯胺酮的合成
2.3α-酰氧基化N,N-二甲基烯胺酮的合成
通过C = C双键裂解进行3个官能化反应
3.1官能化甲基酮的合成
3.2α-酮酰胺,α-酮酸酯和1,2-二酮的合成
3.3 N-磺酰基Am的合成
4全碳芳香支架的构建
4.1苯甲醛的合成
4.2萘的合成
5杂环支架的构建
5.1五元杂环的合成
5.2六元杂环的合成
5.3喹啉的合成
5.4功能化色酮的合成
5.5其他熔融多环杂环的合成
6结论与观点