Abstract
An efficient method for the direct β-acylation of arylidene pyrazolones and thiazolones with acyl chlorides in the presence of a base catalyzed by organophosphanes is reported. A variety of functionalized 4-arylidene pyrazolone and 5-arylidene thiazolone derivatives were prepared under metal-free and mild conditions via a tandem phospha-Michael addition/O-acylation/intramolecular cyclization/rearrangement sequence. Our mechanistic investigations revealed that the reaction is highly stereospecific to provide exclusively cis-isomers, and the methodology can also be scaled up with similar efficacy.
| Original language | English |
|---|---|
| Pages (from-to) | 6868-6872 |
| Number of pages | 5 |
| Journal | Organic Letters |
| Volume | 22 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2020 Sep 4 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Khairnar, P. V., Su, Y. H., Chen, Y. C., Edukondalu, A., Chen, Y. R., & Lin, W. (2020). Organophosphane-catalyzed direct β-acylation of 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides. Organic Letters, 22(17), 6868-6872. https://doi.org/10.1021/acs.orglett.0c02408