基于N,S-缩烯酮的杂环合成的研究

丁奇峰; 杨雅琼; 缪文俊; 黄和; 于杨*; 黄菲*

doi:10.7536/PC180438

化学进展 ›› 2018, Vol. 30 ›› Issue (11) :1615-1623 DOI: 10.7536/PC180438

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基于N,S-缩烯酮的杂环合成的研究

丁奇峰, 杨雅琼, 缪文俊, 黄和, 于杨*, 黄菲*

作者信息 +

Synthesis of Heterocycles Based on Ketene N,S-Acetals

Qifeng Ding, Yaqiong Yang, Wenjun Miao, He Huang, Yang Yu*, Fei Huang*

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文章历史 +

摘要

N，S-缩烯酮是一类重要的有机合成中间体，其官能团的多样性决定了反应的多样性。N，S-缩烯酮的主要反应有与亲核体的共轭加成、与金属有机试剂的选择性加成、环合（五元环或六元环）、还原和缩合等反应，其在杂环合成中具有非常重要的意义。本文主要综述了N，S-缩烯酮的制备及其在参与合成含氮杂环（吡咯、吲哚、吡啶、嘧啶等）、含氧杂环（呋喃、吡喃等）及在多组分反应中的应用，重点介绍了各类反应的普适性、反应机理或衍生化的研究结果，以更好地认识N，S-缩烯酮分子，并期望通过N，S-缩烯酮实现选择性的合成各类所需的杂环化合物，以促进N，S-缩烯酮在杂环合成中的应用。此外，N，S-缩烯酮合成的杂环化合物大部分具有潜在的生物活性，这将促进其在药物化学及药物合成领域的应用和发展。

Abstract

Ketene N,S-acetals are an important class of organic synthesis intermediates, and the diversity of their functional groups determines the diversity of their reactivities. The main reactions with ketene N,S-acetals are the nucleophilic conjugate addition, the selective addition with the organometallic reagents, cyclization (forming a five-membered ring or a six-membered ring), reduction, condensation and other reactions, so it is of great significance in the research of heterocycle synthesis. This review summarizes the general methods for synthesis of ketene N,S-acetals and the research on synthesis of heterocycles from ketene N,S-acetals in the recent years, including the synthesis of N-heterocyclic compounds (pyrrole, indole, pyridine, pyrimidine), O-heterocyclic compounds (furan, pyran) and multi-component reactions. The reaction generality, reaction mechanisms or derivatization results of various types of reactions are also introduced to better understand ketene N,S-acetals molecules and to expect for the selective synthesis of object heterocyclic compounds by ketene N,S-acetals. This will promote the development and applications of ketene N,S-acetals in heterocycle synthesis. In addition, most of the heterocyclic compounds synthesized by ketene N,S-acetals have potential biological activities, and the purpose of this paper is also to promote the development of ketene N,S-acetals in the field of medicinal chemistry and pharmaceutical synthesis.
Contents
1 Introduction
2 General methods for synthesis of ketene N,S-acetals
3 Application of ketene N,S-acetals in organic synthesis
3.1 The synthesis of N-heterocycles
3.2 The synthesis of O-heterocycles
3.3 Multi-component reactions
4 Conclusion

Graphical abstract

关键词

N,S-缩烯酮 / 铜促进 / 含氮杂环 / 含氧杂环 / 多组分反应

Key words

ketene N,S-acetals / copper-mediated / N-heterocycles / O-heterocycles / multi-component reactions

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丁奇峰, 杨雅琼, 缪文俊, 黄和, 于杨*, 黄菲*. 基于N,S-缩烯酮的杂环合成的研究[J]. 化学进展, 2018, 30(11): 1615-1623 DOI:10.7536/PC180438

Qifeng Ding, Yaqiong Yang, Wenjun Miao, He Huang, Yang Yu*, Fei Huang*. Synthesis of Heterocycles Based on Ketene N,S-Acetals[J]. Progress in Chemistry, 2018, 30(11): 1615-1623 DOI:10.7536/PC180438

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