K2CO3-Catalyzed Synthesis of Chromones and 4-Quinolones through the Cleavage of Aromatic C–O Bonds

Phenol-derived electrophiles are favorable substrates because phenols are naturally abundant or can be readily prepared from other aromatic compounds. However, the cleavage of aromatic C–O bonds is a great challenge because of their high energy. K2CO3-catalyzed intramolecular cyclization of 1-(2-alk...

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Bibliographic Details
Published in:Organic letters 2012-06, Vol.14 (11), p.2710-2713
Main Authors: Zhao, Jie, Zhao, Yufen, Fu, Hua
Format: Article
Language:English
Subjects:
4-Quinolones - chemical synthesis
4-Quinolones - chemistry
Carbonates - chemistry
Catalysis
Chromones - chemical synthesis
Chromones - chemistry
Combinatorial Chemistry Techniques
Cyclization
Molecular Structure
Phenols - chemistry
Potassium - chemistry
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Summary:Phenol-derived electrophiles are favorable substrates because phenols are naturally abundant or can be readily prepared from other aromatic compounds. However, the cleavage of aromatic C–O bonds is a great challenge because of their high energy. K2CO3-catalyzed intramolecular cyclization of 1-(2-alkoxyphenyl)-3-akylpropane-1,3-dione and 3-(alkylimino)-1-(2-methoxyphenyl)-2-methylpropan-1-one derivatives via the selective cleavage of aromatic C–O bonds is reported. The corresponding chromone and 4-quinolone derivatives were obtained in reasonable yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300908g