title: A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles.
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.
authors.affiliation: School of Chemistry, University of Hyderabad, Hyderabad 500046, India.
authors.forename: M
authors.initials: M
authors.lastname: Bhanuchandra
authors.forename: Malleswara Rao
authors.initials: MR
authors.lastname: Kuram
authors.forename: Akhila K
authors.initials: AK
authors.lastname: Sahoo
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D002586:Cesium / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007536:Isomerism; D007659:Ketones / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry*
chemical_list: D000480:Alkynes; D002254:Carbonates; D006571:Heterocyclic Compounds; D007659:Ketones; D020005:Propanols; D002586:Cesium; D002244:Carbon; C028255:propargyl alcohol; D009584:Nitrogen; C545311:cesium carbonate