Synthesis of 1,5‐Substituted Iminodibenzo[<i>b</i>,<i>f</i>][1,5]diazocine, an Analogue of Tröger’s Base

Abstract

Abstract A method for the synthesis of 1,5‐disubstituted iminodibenzo[ b , f ][1,5]diazocines is presented. The synthesis is achieved by the metal‐free cyclization of 2‐aminophenyl ketimines using the corresponding 2‐aminophenyl ketone as the catalyst. The synthesis gives new insight into the mechanism of formation of this class of compounds. The presence of potential sites for hydrogen‐bond formation and two aromatic bromine atoms available for functionalization make these targets attractive for further development in supramolecular chemistry. The structure of the complex derived from the iminodibenzo[ b , f ][1,5]diazocine and PdCl 2 was determined by X‐ray crystallography. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2006)