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The reduction of 6-methoxy-9-methyl-11-oxoechiboline using lithium aluminium hydride

journal contribution
posted on 2023-06-08, 19:32 authored by Brian Cox, Brian Robinson
Reduction 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 Chemistry

ISSN

0022-152X

Publisher

Wiley

Issue

1

Volume

25

Page range

271-272

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2015-01-14

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