KHSO4-Assisted Michael Addition-Elimination Reactions of Indole with 3-Dimethylamino-1-phenylprop-2-en-1-ones in Water: An Environmentally Friendly Synthesis of Novel 3-Indolylchalcones

KHSO 4 -assisted Michael addition-elimination reactions of 2-methylindoles and 1,2-dimethylindoles with 3-dimethylamino-1-phenylprop-2-en-1-ones (2) in water, leading to the formation of 3-(2-methyl-1H-indol-3-yl)-1-arylpropenones (3a-e) and 3-(1,2-dimethy-1H-lindol-3-yl)-1-arylpropenones (3f-j) res...

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Bibliographic Details
Published in:Synthetic communications 2013-06, Vol.43 (12), p.1653-1660
Main Authors: Devi, A. Satyapati, Helissey, P., Nongkhlaw, R. L., Vishwakarma, Jai N.
Format: Article
Language:English
Subjects:
Enaminones
indoles
KHSO
Michael addition-elimination reactions
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Summary:KHSO 4 -assisted Michael addition-elimination reactions of 2-methylindoles and 1,2-dimethylindoles with 3-dimethylamino-1-phenylprop-2-en-1-ones (2) in water, leading to the formation of 3-(2-methyl-1H-indol-3-yl)-1-arylpropenones (3a-e) and 3-(1,2-dimethy-1H-lindol-3-yl)-1-arylpropenones (3f-j) respectively in good to excellent yields have been reported. However, cyclodehydration of adducts 3a-f to give carbazoles 4 failed to take place under the reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2012.658946