Catalyst-free synthesis of coumarin-, quinolone- and pyridine-annulated oxazole derivatives

An efficient approach for the synthesis of coumarin-, quinolone- and pyridine-annulated oxazole derivatives has been achieved by direct base-mediated intramolecular carbon–oxygen bond formation in a transition metal catalyst-free protocol. Intramolecular cyclization of o-bromoamides in DMSO in the p...

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Veröffentlicht in:Tetrahedron letters 2012-03, Vol.53 (13), p.1553-1557
Hauptverfasser: Majumdar, K.C., Ganai, Sintu, Nandi, Raj Kumar, Ray, Krishanu
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient approach for the synthesis of coumarin-, quinolone- and pyridine-annulated oxazole derivatives has been achieved by direct base-mediated intramolecular carbon–oxygen bond formation in a transition metal catalyst-free protocol. Intramolecular cyclization of o-bromoamides in DMSO in the presence of Cs2CO3 at 130°C affords heterocycle-annulated oxazole derivatives in high yields via a nucleophilic addition of amide to form the C–O bond.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.01.015