Quinazolines. Part XIV. The absolute configurations of cis- and trans-(+)- and (–)-decahydroquinazolines and 2-amino-octahydroquinazolines

Abstract

cis-2-Benzamidocyclohexanecarboxylic acid was resolved and the absolute configurations of the enantiomers were shown to be (1R,2S)-(–) and (1S,2R)-(+). These were converted into the (4aR,8aS)-trans-(–)- and (4aS,8aR)-trans-(+)-2-amino-3,4,4a,5,6,7,8,8a-octahydroquinazoline sulphates and (4aS,8aR)-(+)-decahydroquinazoline acetate. cis-2-Aminocyclohexanecarbohydrazide was also resolved and the absolute configurations of the enantiomers were shown to be (1R,2S)-(–) and (1S,2R)-(+). These were converted respectively into (4aS,8aS)-cis-(–)- and (4aR,8aR)-cis-(+)-decahydroquinazolines and into (4aS,8aS)-(–)- and (4aR,8aR)-(+)-2-amino-3,4,4a,5,6,7,8,8a-octahydroquinazoline sulphates.