Clayden Jonathan, Hamilton Stuart D, Mohammed Rukhsana T
Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK.
Org Lett. 2005 Aug 18;7(17):3673-6. doi: 10.1021/ol051214u.
Lithiation of N-benzyl pyridine and quinoline carboxamides alpha to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring-containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic beta-lactams. [reaction: see text]
氮原子α位的N-苄基吡啶和喹啉甲酰胺的锂化反应生成阴离子，该阴离子可直接或在通过N-酰化激活环后对吡啶或喹啉环进行分子内进攻。所得含四元、五元或六元环的化合物可被氧化、质子化、烷基化或酰化，以得到一系列多环杂环化合物，包括吡咯并吡啶、吡咯并喹啉、苯并萘啶和氮杂螺环β-内酰胺。[反应：见正文]
