Han X.-D.,Jiang Xi Academic of science |
Wang H.-B.,Jiang Xi Academic of science |
Hu J.-W.,Jiang Xi Academic of science |
Xiong W.,Jiang Xi Academic of science |
And 5 more authors.
Tetrahedron Letters | Year: 2015
A series of 2-pyridone derivatives have been synthesized via a formal [3+3] annulation strategy starting from readily available α-EWG-α-formyl ketene-S,S-acetal 1 and α-carbamoyl ketene-S,S-acetals 2 in the presence of CH3COOH at 80 °C in excellent yields (91-98%). A mechanism involving sequential Baylis-Hillman reaction, intramolecular cycloaddition, Michael addition, and alkylthiol elimination processes for this novel reaction is described in the Letter. In addition, substituted 1-aryl pyridine-2(1H)-ones 4 have also been prepared in high yields via a Cu(OAc)2-mediated three-component reaction of 1, 2, and aryl boronic acid. © 2015 Elsevier Ltd.