羟基二硫缩烯酮Vilsmeier反应 Synthesis 2008, 3633羟基二硫缩烯酮Vilsmeier反应 Synthesis 2008, 3633.pdfVIP

PAPER 3633 Efficient One-Pot Synthesis of 1,3-Disubstituted Pyridin-2(1H)-ones from a-Hydroxyketene S,S-Acetals under Vilsmeier Conditions Synthesis of 1,3-Disubstituted Pyridin-2(1Jun Liu, Deqiang Liang, Mang Wang,* Qun Liu*H)-ones Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China Fax +86(431 E-mail: wangm452@ Received 18 June 2008; revised 7 August 2008 droxyketene S,S-acetals have been successfully applied in Abstract: A facile and efficient one-pot synthesis of 1,3-disubsti- 13a the synthesis of functionalized unsaturated d-lactones, tuted pyridin-2(1H)-ones is developed via a novel cascade reaction 13b of readily available a-hydroxy-a-carbamoyl ketene S,S-acetals substituted 3,4-dihydro-2-pyridones, and 3,4-disubsti- under Vilsmeier conditions (DMF/POCl3), and a mechanism of this tuted dihydrocoumarins.13c As a part of our continuing in- domino reaction is proposed. terest in further synthetic potential of a-hydroxyketene Key words: pyridin-2(1H)-ones, Vilsmeier reagent, a-hydroxy- S,S-acetals and the Vilsmeier–Haack reaction for the syn- ketene S,S-acetals thesis of various heterocycles, in the present work, we ex- amined the reactiv