Xiang Jinbao, Xie Hongxiang, Wen Dongsheng, Dang Qun, Bai Xu
The Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Haiwai St., Changchun, Jilin 130012, PR China.
J Org Chem. 2008 Apr 18;73(8):3281-3. doi: 10.1021/jo702754r. Epub 2008 Mar 21.
The tandem iminium cyclization and Smiles rearrangement of pyridinyloxyacetaldehyde 1 and a primary amine generated a novel pyrido[2,3-e]pyrrolo[1,2-a]pyrazine scaffold. TFA was discovered to be an efficient catalyst in the reactions with aromatic amines, whereas TiCl4 was found to be superior in the case of aliphatic amines. This methodology proved to be efficient in the preparation of a library of diversified pyrido[2,3-e]pyrrolo[1,2-a]pyrazine derivatives.
吡啶氧基乙醛1与伯胺的串联亚胺鎓环化反应和斯迈尔斯重排反应生成了一种新型的吡啶并[2,3-e]吡咯并[1,2-a]吡嗪骨架。研究发现，在与芳香胺的反应中，三氟乙酸（TFA）是一种高效催化剂，而在脂肪胺的反应中，四氯化钛（TiCl4）表现更优。该方法在制备多样化的吡啶并[2,3-e]吡咯并[1,2-a]吡嗪衍生物库方面被证明是有效的。
