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a-(3,7-DIOXA-r-1-AZABICYCLO[3.3.0]OCT-c-5-YL METHOXY)-DIAZINES (I): SYNTHESIS AND STEREOCHEMISTRY. EXTENTION IN s-TRIAZINE SERIES


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 synthesis of the title compounds, consisting in the replacement of chlorine in commercial a-chlorodiazines and cyanuryl chloride by the 3,7-dioxa-r-1-azabicyclo[3.3.0]oct-c-5-ylmethoxy group (Williamson method) is described. The stereochemistry of this new series is analysed in terms of different conformational chirality exhibited in solution (1H DNMR) vs. solid state (X-Ray Diffractometry), meso against chiral forms respectively. In solid state, the inclusion capacity of some chiral networks as well as their supramolecular aggregation is pointed out.

Keywords:

pyrazines, pyrimidines, s-triazines, oxazolidines, NMR, chirality, X-Ray Diffractometry.

Code [ID]:

CSCC6200607V01S01A0002 [0001061]

Full paper:

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