Synthesis of 4-styrylquinolines via direct oxidative C3-alkenylation of anthranils under Pd(II) catalysis.

Autor: Awasthi A; Department of Biological and Synthetic Chemistry, Center of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow 226014, Uttar Pradesh, India. dktiwari.@cbmr.res.in.; Department of Chemistry, Institute of Science, Banaras Hindu University, 221005, Varanasi, Uttar Pradesh, India., Tiwari K; Department of Biological and Synthetic Chemistry, Center of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow 226014, Uttar Pradesh, India. dktiwari.@cbmr.res.in., Yadav P; Department of Biological and Synthetic Chemistry, Center of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow 226014, Uttar Pradesh, India. dktiwari.@cbmr.res.in.; Department of Chemistry, Institute of Science, Banaras Hindu University, 221005, Varanasi, Uttar Pradesh, India., Bhowmick S; Department of Biological and Synthetic Chemistry, Center of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow 226014, Uttar Pradesh, India. dktiwari.@cbmr.res.in., Tiwari DK; Department of Biological and Synthetic Chemistry, Center of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow 226014, Uttar Pradesh, India. dktiwari.@cbmr.res.in.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Feb 15; Vol. 60 (15), pp. 2054-2057. Date of Electronic Publication: 2024 Feb 15.
DOI: 10.1039/d3cc05790a
Abstrakt: The palladium-catalyzed oxidative C3-alkenylation of anthranils (2,1-benzisoxazoles) with various styrenes has been successfully achieved. The C3-alkenylated anthranils were subsequently utilized in a [4+2]-cycloaddition with in situ generated α,β-unsaturated ketones leading to the synthesis of a diverse range of olefin-containing quinolines. Notably, this reaction exclusively yielded mono-alkenylated products with E -selectivity. The optimized catalytic conditions were compatible with a wide variety of substituted olefins and anthranils, forming various C3-alkenylated anthranils with good yields. To showcase the application of the present methodology, the C3-alkenylated anthranils have been employed as synthons to access a wide range of substituted quinolines.
Databáze: MEDLINE