A Catalytic Homo-Nazarov Cyclization Protocol for the Synthesis of Heteroaromatic Ring-Fused Cyclohexanones

A general protocol for the catalytic homo-Nazarov cyclization of cyclopropyl heteroaryl ketones has been developed, which employs indium triflate as the promoter. A range of heteroaromatic ring-fused cyclohexanones was synthesized in 56−91% yield using this protocol. An example of a tandem cycloprop...

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Bibliographic Details
Published in:Organic letters 2011-04, Vol.13 (8), p.1952-1955
Main Authors: Phun, Lien H, Patil, Dadasaheb V, Cavitt, Marchello A, France, Stefan
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Cyclohexanones - chemical synthesis
Molecular Structure
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Summary:A general protocol for the catalytic homo-Nazarov cyclization of cyclopropyl heteroaryl ketones has been developed, which employs indium triflate as the promoter. A range of heteroaromatic ring-fused cyclohexanones was synthesized in 56−91% yield using this protocol. An example of a tandem cyclopropanation/homo-Nazarov cyclization is also reported in which the one-pot yield is greater than the overall yield of the two individual steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200305n