Substrate Divergent 4π/6π Electrocyclization of CF<sub>3</sub>‐Quinolone Heterodendralenes

Herein, a substrate‐divergent 4π/6π electrocyclization of hitherto unknown CF 3 ‐heterodendralenes is disclosed, generated in situ from the 4‐methyl‐3‐trifluoroacetyl quinolones. The reaction favors 4π‐electrocyclization in the presence of a phenyl substituent, producing cyclobuta[ c ]quinolones featuring a challenging CF 3 ‐all‐carbon quaternary stereocenter. Conversely, vinyl substitution promotes 6π‐electrocyclization to provide CF 3 ‐dihydro‐phenanthridones.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-08-14
DOI
https://doi.org/10.1002/ejoc.202500500
Citations
1
Primary Topic
Computer Science and Engineering
Type
article
Field-Weighted Citation Impact
2.48

Funders

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article

Substrate Divergent 4π/6π Electrocyclization of CF3‐Quinolone Heterodendralenes

1 citations
European Journal of Organic Chemistry
Computer Science and Engineering
2.48
article

Substrate Divergent 4π/6π Electrocyclization of CF3‐Quinolone Heterodendralenes

article en
1 citations

Abstract

Herein, a substrate‐divergent 4π/6π electrocyclization of hitherto unknown CF 3 ‐heterodendralenes is disclosed, generated in situ from the 4‐methyl‐3‐trifluoroacetyl quinolones. The reaction favors 4π‐electrocyclization in the presence of a phenyl substituent, producing cyclobuta[ c ]quinolones featuring a challenging CF 3 ‐all‐carbon quaternary stereocenter. Conversely, vinyl substitution promotes 6π‐electrocyclization to provide CF 3 ‐dihydro‐phenanthridones.

European Journal of Organic ChemistryVol. 28(38)
Indian Institute of Chemical Technology (IN), Academy of Scientific and Innovative Research (IN)
Council of Scientific and Industrial Research, India
Openalex Percentile: Top 6%
Computer Science and Engineering
2.48
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