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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

Issue:

SCSCC6, Volume VII, No. 1

Section:

Volume VII - No. 1 (2006)

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.

Keywords:

pyrazines, pyrimidines, pyridazines, oxazolidines, metallation, cross-coupling, NMR, chirality.

Code [ID]:

CSCC6200607V01S01A0003 [0001062]

Full paper:

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