Novel analgesics and molecular rearrangements in the morphine–thebaine group. Part XII. Derivatives of 7-amino-6,14-endo-etheno-tetrahydrothebaine
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 18,p. 2235-2236
- https://doi.org/10.1039/j39690002235
Abstract
The tetrahydrothebaine ester (1) has been converted by the Curtius reaction into 7α-amino-6,14-endo-etheno-tetrahydrothebaine (3; R = H) and its 6,14-ethano-analogue. The amine and its 1-chloro-derivative have also been prepared from the ketone (6) by the Schmidt reaction. The amine has been rearranged to the benzazocine (4) by methylation and Hofmann degradation, and its 1-chloro-derivative has been rearranged by nitrous acid to the ketone (8).Keywords
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