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

Cox, Brian and Robinson, Brian (1988) The reduction of 6-methoxy-9-methyl-11-oxoechiboline using lithium aluminium hydride. Journal of Heterocyclic Chemistry, 25 (1). pp. 271-272. ISSN 0022-152X

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Abstract

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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Depositing User: Tom Gittoes
Date Deposited: 14 Jan 2015 10:57
Last Modified: 14 Jan 2015 10:57
URI: http://sro.sussex.ac.uk/id/eprint/52130
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