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

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. Ar...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-05, Vol.10 (17), p.3538-3555
Main Authors: Bhanuchandra, M, Kuram, Malleswara Rao, Sahoo, Akhila K
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Carbon - chemistry
Carbonates - chemistry
Catalysis
Cesium - chemistry
Heterocyclic Compounds - chemistry
Isomerism
Ketones - chemistry
Nitrogen - chemistry
Oxidation-Reduction
Propanols - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25165e