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The reduction of 6-methoxy-9-methyl-11-oxoechiboline using lithium aluminium hydride
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posted on 2023-06-08, 19:32 authored by Brian Cox, Brian RobinsonReduction of 6-methoxy-9-methyl-11-oxoechiboline 1a using lithium aluminium hydride in boiling tetrahydrofuran under reflux affords 6-methoxy-9-methylechiboline. However, attempts to effect a similar reduction of a suspension of compound 1a in boiling diethyl ether under reflux, in which it is only very slightly soluble, were unsuccessful and when, under these conditions, a Soxhlet apparatus was employed to effect dissolution, an unexpected reductive ring scission occurred along with reduction of the carbonyl group to afford 4a-(2-aminoethyl)-6-methoxy-9-methyl-1,2,3,4,4a,9a-hexahydrocarbazole 3.
History
Publication status
- Published
Journal
Journal of Heterocyclic ChemistryISSN
0022-152XPublisher
WileyExternal DOI
Issue
1Volume
25Page range
271-272Department affiliated with
- Chemistry Publications
Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2015-01-14Usage metrics
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