A convenient approach to β-heteroarylated (C-N bond) ketones from Cs CO promoted reaction between propargyl alcohols and nitrogen-heterocycles
Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 10, Issue: 17, Page: 3538-3555
2012
- 19Citations
- 7Captures
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Article Description
An efficient and direct approach to β-heteroarylated (C-N bond) ketones is demonstrated. Base promoted redox isomerization of propargyl alcohol to α,β-unsaturated ketone followed by conjugate addition to NH-heteroarenes affords a wide range of β-heteroarylated ketones in good to excellent yields. Aryl, heteroaryl, alkyl C(sp), and terminal alkynes containing unactivated propargyl alcohols effectively undergo redox-isomerization conjugate addition (RICA) with NH-heteroarenes. Reaction of 3-substituted pyrazoles or indazole with propargyl alcohols enables highly regioselective products. A diverse range of NH-bearing nucleophiles such as: pyrazoles, imidazole, triazoles, pyrrole, indoles and aniline participate in this reaction and deliver the corresponding β-heteroarylated ketones. © 2012 The Royal Society of Chemistry.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84859789500&origin=inward; http://dx.doi.org/10.1039/c2ob25165e; http://www.ncbi.nlm.nih.gov/pubmed/22441201; https://xlink.rsc.org/?DOI=c2ob25165e; https://dx.doi.org/10.1039/c2ob25165e; https://pubs.rsc.org/en/content/articlelanding/2012/ob/c2ob25165e
Royal Society of Chemistry (RSC)
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