基于N,S-缩烯酮的杂环合成的研究

Synthesis of Heterocycles Based on Ketene N,S-Acetals

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。

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),Oheterocyclic 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.