One-Pot Ring-Closing Metathesis (RCM)/Oxidation by an Assisted Tandem Ruthenium Catalysis
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5j–5l, 5n, into the corresponding 2-quinolones 6j–6l,
6n in good to excellent yields. However, 4m, with a
substituent on the 6-position, was converted to the
corresponding 2-quinolone in moderate yield
(entry 5), probably due to steric hindrance. Therefore,
this is a substrate-dependent reaction.
These results suggest that after the RCM process,
the Ru carbene catalyst seems to be converted to an-
other Ru species, which might catalyze the oxidation
of the methylene adjacent to the nitrogen of the 1,2-
dihydroquinoline.
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Finally, the best conditions (Table 1, entry 20) were
applied to our medicinal substrate 1. As a result, the
expected 3 was successfully obtained in 83% yield.
In summary, we have developed a one-pot RCM/
oxidation methodology to produce various 2-quino-
lones from 2-vinyl-N-allylaniline derivatives. This is
another example of a non-metathesis reaction using a
ruthenium carbene catalyst.
Experimental Section
General Procedure for the Preparation of 2-
Quinolone Derivatives
To a solution of an a,w-diene (0.1 mmol) in benzene
(10 mL) was added catalyst B (8.5 mg, 10 mol%) and the
mixture was refluxed for 30 min under argon. The mixture
was cooled to room temperature and TBHP (68% in water;
0.029 mL, 0.2 mmol) was added. After 1 hour, the solvent
was evaporated under reduced pressure. The obtained resi-
due was subjected to column chromatography (neutral silica
gel, hexane/AcOEt=5:1) to give the products.
Acknowledgements
This work was supported by a Grant-in-Aid for Scientific Re-
search on Innovative Areas “Molecular Activation Directed
toward Straightforward Synthesis” from the Ministry of Edu-
cation, Culture, Sports, Science and Technology, Japan.
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Adv. Synth. Catal. 2011, 353, 2676 – 2680
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