Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Isolation of a Novel Oxygenated Dimer of 3-Methylindole, 5aβ (H), 11aα (H)-12β-Hydroxy-10bβ, 12α-dimethyl-5a, 10b, 11a, 12-tetrahydro-6H-oxazolo-[3, 2-a : 4, 5-b'] diindole, and Structure Determination of Its Acetylated Derivative
MASAFUMI GOTOKOUJI MORIYOSHITAKA KURODATOMOYA SAKAITASUKU ITO
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Keywords: dynamic NMR
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1985 Volume 33 Issue 5 Pages 1878-1888

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Abstract
A new oxygenated dimer of 3-methylindole was isolated from the reaction mixture obtained by oxygenation of 3-methylindole in the presence of a sterically crowded cobalt catalyst, N, N'-(cis-1, 2-cyclohexylene) bis (3-tert-butylsalicylideneaminato) cobalt (II). X-Ray crystal structure determination of its acetylated derivative revealed it to be 6-acetyl-5aβ (H), 11aα (H)-12β-hydroxy-10bβ, 12α-dimethyl-5a, 10b, 11a, 12-tetrahydro-6H-oxazolo [3, 2-a : 4, 5-b'] diindole, with a novel C6-C4N-C3NO-C4N-C6 ring system. Two conformers due to restricted rotation of the acetyl group of the acetylated derivative was observed by temperature-dependent 1H-nuclear magnetic resonance spectroscopy.
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© The Pharmaceutical Society of Japan
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