
%0 Journal Article
%A Mooney, BA 
%A Prager, RH 
%A Ward, AD 
%T Central nervous system active compounds. V. Claisen rearrangement products of allyl vinyl ethers obtained from caprolactam derivatives
%J Australian Journal of Chemistry
%D 1980/12/01
%V 33
%N 12
%P 2717-2728
%K 
%R https://doi.org/10.1071/CH9802717
%U https://www.publish.csiro.au/paper/CH9802717 
%X A series of allyloxy unsaturated tetrahydroazepinones has been prepared and their Claisen rearrangements have been investigated. The 4-allyloxy compounds (4a-e) rearranged thermally to give the 3-substituted hexahydro derivatives (9). In some cases further reaction products were obtained, particularly when higher temperatures were used. Rearrangement of the 4-propargyloxy system (4f) proved more complicated, and N-allyl-2,3,4,5-tetrahydro-1H-azepin-2-one derivatives (21a,b) were unreactive. Alkylation of the hexahydroazepine-2,4-dione system (3) with various allyl halides gave mixtures of the 3-mono-(20) and the 3,3-di-substituted (19) products. The unsaturated ethers generally showed marked muscular depression on the central nervous system of mice, while their rearrangement products were only weakly depressant. 
