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 |
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Pages (from-to) | 6868-6872 |
Number of pages | 5 |
Journal | Organic Letters |
Volume | 22 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2020 Sept 4 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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CCDC 2006528: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Su, Y. (Contributor), Chen, Y. (Contributor), Edukondalu, A. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc25byq6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc25byq6&sid=DataCite
Dataset
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CCDC 1960460: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Su, Y. (Contributor), Chen, Y. (Contributor), Edukondalu, A. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc23t0nm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23t0nm&sid=DataCite
Dataset
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CCDC 1972709: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Su, Y. (Contributor), Chen, Y. (Contributor), Edukondalu, A. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc246rsx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc246rsx&sid=DataCite
Dataset