Regioselective synthesis of 2-carbonyl furans in a one pot three component reaction

[Display omitted] •Multicomponent one pot reaction.•Catalyst free.•Ambient temperature.•Selective product formation.•Excellent yields. Regioselective synthesis of 2-benzoyl-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-ones have been accomplished through a novel protocol involving β-amino enone, N-chloro...

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Bibliographic Details
Published in:Tetrahedron letters 2018-11, Vol.59 (47), p.4168-4171
Main Authors: Kale, Ashok, Medishetti, Nagaraju, Nanubolu, Jagadeesh Babu, Atmakur, Krishnaiah
Format: Article
Language:English
Subjects:
1,3-diketone
Furan scaffolds
N-chlorosucinimide
SNV reaction
β-Amino enone
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Summary:[Display omitted] •Multicomponent one pot reaction.•Catalyst free.•Ambient temperature.•Selective product formation.•Excellent yields. Regioselective synthesis of 2-benzoyl-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-ones have been accomplished through a novel protocol involving β-amino enone, N-chlorosuccinimide and dimedone in a one pot catalyst-free reaction at an ambient temperature. On the other hand, the same reaction when conducted with two equivalents of N-chlorosuccinimide under similar reaction conditions, exclusive formation of 2-benzoyl-3-(dimethylamino)-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-ones were observed. Simple and metal-free reaction conditions, selective product formation and excellent yields are the advantages of this protocol.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.10.021