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 PdCl2 was determined by X-ray crystallography.

Synthesis of 1,5-Substituted Iminodibenzo[b,f][1,5]diazocine, an Analogue of Troger’s Base

FABRIS, Fabrizio;DE LUCCHI, Ottorino;
2006

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 PdCl2 was determined by X-ray crystallography.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10278/29121
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