Bromination and iodination of 6H,12H-5, 11-methanodibenzo[b,f][1,5] diazocine: A convenient entry to unsymmetrical analogs of Tröger's base

6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine can easily be prepared from aniline and paraformaldehyde. Its reactions with either N-bromosuccinimide (NBS) or with iodine monochloride (ICl) in the presence of a suitable activator smoothly afford 2-bromo- and 2-iodo- derivatives, respectively. The combination of these halogenation methods provides access to the 8-bromo-2-iodo derivative, which is an interesting and otherwise inaccessible intermediate for the synthesis of unsymmetrical analogs of Tröger's base. The reported halogenations represent the first examples of electrophilic substitution in 6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocine. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.SCOPUS: ar.jFLWINinfo:eu-repo/semantics/publishe

Homologation of heterocycles by a sequential reductive opening lithiation-electrophilic substitution-cyclization

The development of new methodologies for the conversion of simple reactants into more complex compounds is the main goal of synthetic organic chemistry. For instance, transforming readily available small heterocycles into much less common medium-sized rings would be of great interest, because many biological active compounds possess medium-sized heterocyclic units in their structure. Thus, synthetic approaches to heterocyclic compounds require the development of methodology for easily repeatable heterocycle homologation and multicarbon ring expansion