Efficient synthesis of 3‐sulfonyl‐1,2‐dihydroquinolines via tandem aza‐Michael addition/cyclizations of N ‐acyl‐protected 2‐aminobenzaldehyde with vinyl sulfones

A mild and effective method for the synthesis of 3‐sulfonyl‐1,2‐dihydroquinolines from N ‐acyl‐protected 2‐aminobenzaldehyde with vinyl sulfones has been established. This reaction could rapidly proceed and exhibit different reactivity when employed the vinyl sulfones as nucleophile on aza‐Michael a...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2023-11, Vol.60 (11), p.1872-1882
Main Authors: Wang, Kai‐Kai, Liu, Guo‐Yan, Li, Yan‐Li, Zhou, Wen‐Wen, Ye, Jun‐Wei, Jia, Yan‐Zhi, Chen, Rongxiang, Wang, Zhan‐Yong
Format: Article
Language:English
Subjects:
Crystal structure
Nucleophiles
Structural analysis
Sulfones
Synthesis
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Summary:A mild and effective method for the synthesis of 3‐sulfonyl‐1,2‐dihydroquinolines from N ‐acyl‐protected 2‐aminobenzaldehyde with vinyl sulfones has been established. This reaction could rapidly proceed and exhibit different reactivity when employed the vinyl sulfones as nucleophile on aza‐Michael addition/cyclization reaction, allow for the production of 1,2‐DHQs in high yields up to 95%. In addition, the chemical structure of the product was confirmed by x‐ray single‐crystal structure analysis.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4729