摘要
咪唑并吡啶[1,5-a]类化合物是一类具有环合氮类的杂环化合物,在自然界中并不广存在.但是近些年来的研究发现,这类杂环包括它的衍生物广泛地应用于光学材料和生物医药领域中.我们选用吡啶苄胺和芳香醛作为反应底物,在碘和过氧叔丁醇催化下,反应能够得到咪唑并[1,5-a]吡啶类衍生物,而且我们研究当使用吡啶苄胺α位有取代基的底物时,也能够得到相应的目标产物.因此,利用这种方法我们能同时制备得到3-芳基化的咪唑并吡啶[1,5-a]类化合物和1,3-二芳基化的咪唑并[1,5-a]吡啶类化合物.而且,该发展起来的方法具有操作简单,条件温和等特点.
Imidazo[1,5-α]pyridines represent an important class ofheterocyclic compounds because of their largely potential application in photophysical and biological areas. These substances have been widely investigated in the context of organic light-emitting diodes （OLED） and organic thinlayer field effect transistors （FET）. Furthermore, they have been explored in a wide range of potential pharmaceutical applications, including H1V-protease inhibitors, and Thromboxane A2 synthesis in- hibitors. However, literature survey found that only some strategies for the synthesis of imidazo[1,5-α]pyridine derivatives were reported. Traditionally, substituted imidazo[1,5-α]pyridines were accessed via Vilsmeier-type cyclizations of N-2-pyridylmethyl amides. Recently, Mural＇s group reported several methods for the construction of imidazo-[1,5-α]pyridine rings. Although these methods provided useful access to substituted imidazo[l,5-α]pyridine derivatives, they suffered from some drawbacks, such as the use of strong acid and high temperature, moreover, study on the preparation of 3-arylated imi- dazo[1,5-α]pyridines and 1,3-diarylated imidazo[l,5-α]pyridines in a procedure is rare. Therefore, developing more efficient and practical protocols for the preparation of 3-arylated imidazo[1,5-α]pyridines and 1,3-diarylated imidazo[1,5-α]pyridines still are highly desirable. As part of a program targeting new methods for constructing some useful heterocycles probably found application in pharmaceutical and industry areas. We chose pyridin-2-ylmethanamine and aldehydes as the reaction substrates to achieve the synthesis of imidazo[1,5-α]pyridines in the presence of iodine and TBHP. Moreover, a-substituted pyridin-2-ylmethanamine used as substrate reacted with aldehydes to also provide 1,3-diarylated imidazo[1,5-α]pyridines. Therefore, 3-aryl imidazo[1,5-α]pyridines and 1,3-diaryl imidazo[1,5-α]pyridines can be obtained through this method. Herein, we report a simple and efficient iodine-catalyzed synthesis of 3-substit
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
2013年第12期1603-1606,共4页
Acta Chimica Sinica
基金
国家自然科学基金(Nos.21172205
21272222)资助~~
关键词
碘催化
氧化
串联环化
杂环合成
咪唑并[1
5-α]吡啶
iodine catalyze
oxidation
tandem cyclization
heterocycles syntheses
imidazo[ 1,5-a]pyridines
