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- Title
Cyclization of Cyanoethylated Ketones.
- Authors
Bergman, Jan; Stensland, Birgitta
- Abstract
δ-Cyanoketones are quickly cyclized with KOtBu to 3-aminocyclohex-2-enone derivatives, which in turn will give substituted indoles when treated with oxalyl chloride. Thus, 3-amino-6,6-dimethylcyclohex-2-enone gave 3-chloro-6,6-dimethyl-2,5,6,7-tetrahydroindole-2,5-dione, whose structure was corroborated by X-ray crystallography, whereas the corresponding molecule without the blocking gem-dimethyl groups, 3-aminocyclohex-2-enone, gave via hydrogen shifts 6-chloro-3-hydroxyoxindole.
- Subjects
KETONE synthesis; INDOLE derivatives; X-ray crystallography; OXALYL chloride; NUCLEAR magnetic resonance spectroscopy; DIMETHYL sulfoxide
- Publication
Journal of Heterocyclic Chemistry, 2014, Vol 51, Issue 1, p1
- ISSN
0022-152X
- Publication type
Article
- DOI
10.1002/jhet.2048