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Synthesis 2008(22): 3633-3638  
DOI: 10.1055/s-0028-1083198
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient One-Pot Synthesis of 1,3-Disubstituted Pyridin-2(1H)-ones from α-Hydroxyketene S,S-Acetals under Vilsmeier Conditions

Jun Liu, Deqiang Liang, Mang Wang*, Qun Liu*
Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China
Fax: +86(431)85099759; e-Mail: wangm452@nenu.edu.cn;
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Publication History

Received 18 June 2008
Publication Date:
23 October 2008 (online)

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Abstract

A facile and efficient one-pot synthesis of 1,3-disubstituted pyridin-2(1H)-ones is developed via a novel cascade reaction of readily available α-hydroxy-α-carbamoyl ketene S,S-acetals under­ Vilsmeier conditions (DMF/POCl3), and a mechanism of this domino reaction is proposed.

Key words

pyridin-2(1H)-ones - Vilsmeier reagent - α-hydroxy­ketene S,S-acetals

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Crystal data for 3a: C14H13NO2S, colorless crystal, M = 259.31, monoclinic, space group P21, a = 5.6429(13), b = 12.163(3), c = 9.504(2), Å, V = 652.3(3) ų, α = 90.00, β = 90.00, γ = 90.00, Z = 2, T = 293 (2) K, F 000 = 272, R1 = 0.0428, wR2 = 0.1077. CCDC 690433 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.