130655-36-6Relevant academic research and scientific papers
Assembly of four diverse heterocyclic libraries enabled by prins cyclization, Au-catalyzed enyne cycloisomerization, and automated amide synthesis
Cui, Jiayue,Chai, David I.,Miller, Christopher,Hao, Jason,Thomas, Christopher,Wang, Jingqi,Scheidt, Karl A.,Kozmin, Sergey A.
, p. 7435 - 7470 (2012/11/06)
We describe a unified synthetic strategy for efficient assembly of four new heterocyclic libraries. The synthesis began by creating a range of structurally diverse pyrrolidinones or piperidinones. Such compounds were obtained in a simple one-flask operation starting with readily available amines, ketoesters, and unsaturated anhydrides. The use of tetrahydropyran-containing ketoesters, which were rapidly assembled by our Prins cyclization protocol, enabled efficient fusion of pyran and piperidinone cores. A newly developed Au(I)-catalyzed cycloisomerization of alkyne-containing enamides further expanded heterocyclic diversity by providing rapid entry into a wide range of bicyclic and tricyclic dienamides. The final stage of the process entailed diversification of each of the initially produced carboxylic acids using a fully automated platform for amide synthesis, which delivered 1872 compounds in high diastereomeric and chemical purity.
A PRACTICAL ROUTE TO SPIRO-TYPE HETEROCYCLES RELATED TO ERYTHRINAN
Tsuda, Yoshisuke,Sakai, Yuki,Kaneko, Mari,Ishiguro, Yukie,Isobe, Kimiaki,et al.
, p. 431 - 436 (2007/10/02)
A new method synthesizing spiro-type heterocycles by intramolecular cyclization of 3,3-disubstituted dioxopyrrolines was presented.The method is particularly useful in synthesizing erythrinans and has the following advantages: 1) it is of short steps with high yield ( one-pot reaction is possible ), 2) an activating group at ring A is not necessary, and 3) the procedure can be carried out without protection of phenolic hydroxyl groups.Wide applicability of this method was also shown by synthesizing C-nor and C-homoerythrinans, and other variants which carry heterocycles at ring A instead of benzenoids.
