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
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.