Central nervous system active compounds. V. Claisen rearrangement products of allyl vinyl ethers obtained from caprolactam derivatives
- 1 January 1980
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 33 (12) , 2717-2728
- https://doi.org/10.1071/ch9802717
Abstract
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.Keywords
This publication has 3 references indexed in Scilit:
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