A new enlargement methodology for the preparation of 2H-1-and 2H-3-benzazepin-2-one derivatives

作者：Jean Gerard Ludivine; Pauvert Mickael; Collet Sylvain; Guingant Andre^*; Evain Michel

来源：Tetrahedron, 2007, 63(46): 11250-11259.

DOI：10.1016/j.tet.2007.08.094

• ring enlargement
• 2H-1-and 2H-3-benzazepin-2-one derivatives

An investigation of the one-carbon homologation of some 1-tribromomethyl-isoquinoline and 2-tribromomethyl-quinoline derivatives was conducted. Under the influence of an aqueous solution of silver nitrate in the presence of a nucleophilic species (MeOH, H2O, EtNH2), these derivatives led to the respective expanded heterocycles, 2H-1- and 2H-3-benzazepin-2-one derivatives. A mechanism for this novel ring enlargement involving initial formation of an aziridinium, and its subsequent opening to form a stabilized benzylic carbocation, is proposed to explain the results.

• 出版日期2007-11-12