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Synthesis of 1,5‐Substituted Iminodibenzo[ b , f ][1,5]diazocine, an Analogue of Tröger’s Base
Author(s) -
Leganza Alessandro,
Bezze Chiara,
Zonta Cristiano,
Fabris Fabrizio,
De Lucchi Ottorino,
Linden Anthony
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600167
Subject(s) - chemistry , supramolecular chemistry , ketone , bromine , catalysis , hydrogen bond , stereochemistry , base (topology) , combinatorial chemistry , crystal structure , crystallography , molecule , organic chemistry , mathematical analysis , mathematics
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 & Co. KGaA, 69451 Weinheim, Germany, 2006)