A convenient approach to β-heteroarylated (C–N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles??

Organic & Biomolecular Chemistry Pub Date: 2012-03-01 DOI: 10.1039/C2OB25165E

Abstract

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.

Graphical abstract: A convenient approach to β-heteroarylated (C–N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles
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