a-(3,7-DIOXA-r-1-AZABICYCLO[3.3.0]OCT-c-5- YLMETHOXY)-DIAZINES (II): FUNCTIONALISATION VIA DIRECTED ORTHO-METALLATION AND CROSS-COUPLING REACTIONS
BERGHIAN CAMELIA(1)AND(2), PLÉ NELLY(2), TURCK ALAIN(2), DARABANTU MIRCEA1, (2)
(1)DEPARTMENT OF ORGANIC CHEMISTRY, “BABES-BOLYAI” UNIVERSITY, 11 ARANYI JÀNOS STR., RO-400028 CLUJ-NAPOCA, ROMANIA, DARAB@CHEM.UBBCLUJ.RO (2)INSTITUT DE RECHERCHE EN CHIMIE ORGANIQUE FINE (I.R.C.O.F.), UNIVERSITÉ DE ROUEN, BP 08, F-76131 MONT SAINT-AIGNA
Abstract
The functionalisation of the title compounds via regioselective Directed ortho-Metallation (DoM), cross-coupling and the compatibility of the 3,7-DiOxa-r-1-AzaBicyclo[3.3.0]Oct-c-5-ylmethoxy system (DOABO-CH2O) to the reactions typical conditions are preliminarily reported. Its role as Directed ortho-Metallation Group (DoMG) is examined. The chelating ability of some functionalised terms as DOABO-CH2O substituting chiral diarylmethanols and polyaza analogous of 2,6-terpyridine is discussed as intramolecular steric relationships determining configuration and aptitude to bind selectively transition metals respectively.