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The Reaction of Indole Magnesium Bromide with Ketones I. The Reaction of Indole Magnesium Bromide with Cyclohexanone
Author(s) -
Zee ShengHsu,
Kuo KuangMing
Publication year - 1977
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.197700010
Subject(s) - chemistry , cyclohexanone , magnesium bromide , anisole , indole test , bromide , magnesium , cyclohexanol , benzene , organic chemistry , cyclohexane , cyclohexene , ether , medicinal chemistry , catalysis
Indole magnesium bromide, produced by reacting indole with n ‐butyl magnesium bromide in ether, was reacted with cyclohexanone at ice or room temperature to yield 1‐(indol‐I‐yl)‐cyclohexanol (I), which is unstable and may be decomposed easily into indole and cyclohexanone in acidic condition. Indole magnesium bromide reacted with cyclohexanone in refluxing benzene or in anisole at 80°C, to form two products, 1‐(indol‐3‐yl)‐cyclohexanol (II) and 1‐(indol‐3‐yl)‐cyclohexene (III). (II) could be converted to (III) by heating (II) in phosphoric acid. Reaction of III with maleic anhydride gave a Diels‐Alder adduct (IV). Reaction of indole magnesium bromide with cyclohexanone in anisole at 130°C yielded (III) and a trimolecular condensation product of cyclohexanone (V).