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. 2013 Dec 9;52(50):13280-3.
doi: 10.1002/anie.201308127. Epub 2013 Nov 12.

2-Aminobenzaldehydes as versatile substrates for rhodium-catalyzed alkyne hydroacylation: application to dihydroquinolone synthesis

Matthias Castaing  1 , Sacha L Wason, Beatriz Estepa, Joel F Hooper, Michael C Willis
Affiliations

2-Aminobenzaldehydes as versatile substrates for rhodium-catalyzed alkyne hydroacylation: application to dihydroquinolone synthesis

Matthias Castaing et al. Angew Chem Int Ed Engl. .
No abstract available

Keywords: aldehydes; amines; dihydroquinolones; enones; rhodium catalysis.

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Figures

Scheme 1
Scheme 1
Chelation-free (a) and chelation-controlled intermolecular alkyne hydroacylation (b). The most common chelating aldehyde motifs are also shown (3–7), along with the 2-aminobenzaldehyde framework 8 and examples demonstrating the ubiquity of the 2-amino-carbonyl unit in biologically significant heterocycles.
Scheme 2
Scheme 2
Variation of the 2-aminobenzaldehyde coupling partner in Rh-catalyzed hydroacylation reactions with phenylacetylene. Reaction conditions: 8 (1.0 equiv), phenylacetylene (1.5 equiv), [Rh(nbd)2]BF4 (5 mol %), dcpm (5 mol %), MeCN (10 mol %), acetone (0.15 m), 55 °C. Yields of isolated products are given. DMB=3,4-dimethoxybenzyl.
Scheme 3
Scheme 3
Variation of the alkyne coupling partner in Rh-catalyzed hydroacylation reactions with aminobenzaldehydes 8 b and 8 c. Reaction conditions: 8 b or 8 c (1.0 equiv), alkyne (1.5 equiv), [Rh(nbd)2]BF4 (5 mol %), dcpm (5 mol %), MeCN (10 mol %), acetone (0.15 m), 55 °C. Yields of isolated products are given. [a] Regioisomeric ratio >20:1, determined by 1H NMR spectroscopy.
Scheme 4
Scheme 4
Conversion of amino-substituted enones 9 into 4-quinolones 10. Method A: 2-amino-aryl enone (1.0 equiv), SbCl3 (0.3 equiv), MeCN (0.3 m), 55 °C. Method B: 2-amino-aryl enone (1.0 equiv), TfOH (3.0 equiv), CH2Cl2 (0.1 m), 25 °C; followed by SbCl3 (0.3 equiv), MeCN (0.3 m), 55 °C. [a] d.r.=3:1, determined by 1H NMR spectroscopy. [b] d.r.=4:1, determined by 1H NMR spectroscopy. Cy=cyclohexyl.
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