Department of Chemistry and Biochemistry, The Texas Institute for Drug and Diagnostic Development, The University of Texas at Austin, Austin, Texas 78712, USA.
Org Lett. 2011 Jun 17;13(12):3102-5. doi: 10.1021/ol201010s. Epub 2011 May 20.
A collection of structurally diverse, polyheterocyclic scaffolds comprising a 2-arylpiperidine subunit were synthesized using a Mannich-type multicomponent assembly process, followed by appropriately sequenced ring-forming reactions. An improved procedure for removal of N-4-pentenoyl groups was developed; one-pot sequences for tandem urea/thiourea formation and cyclization and tandem enolate arylation/alkylation were discovered. A novel entry to bridged tetrahydroquinoline scaffolds exploiting A(1,3) strain was also invented. Derivatization of several scaffolds was achieved by cross-coupling and N-functionalization.
采用Mannich 型多组分组装反应,随后进行适当的环化反应,合成了包含 2-芳基哌啶结构单元的结构多样的多杂环支架。开发了一种改进的去除 N-4-戊烯酰基的方法;发现了一锅法串联脲/硫脲形成和环化以及串联烯醇盐芳基化/烷基化反应。还发明了一种利用 A(1,3)应变的新型桥连四氢喹啉支架的新方法。通过交叉偶联和 N-官能化实现了几种支架的衍生化。