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RESEARCH ARTICLE
Contents Vol 63(8)

A Facile and Divergent Synthesis of Substituted Pyridine-2,4(1H,3H)-diones and 4H-Thiopyran-4-ones from α-Alkenoyl-α-carbamoyl Ketene-S,S-acetals

Jinying Liu A , Xiaolan Fu A , Yang Zhou B , Guangyuan Zhou B , Yongjiu Liang B and Dewen Dong A B C
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Northeast Normal University, Changchun, 130024, China.

B Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China.

C Corresponding author. Email: dongdw663@nenu.edu.cn

Australian Journal of Chemistry 63(8) 1267-1271 https://doi.org/10.1071/CH09489
Submitted: 13 September 2009  Accepted: 22 October 2009   Published: 10 August 2010

Abstract

A facile and divergent synthesis of substituted pyridine-2,4(1H,3H)-diones and 4H-thiopyran-4-ones from readily available α-alkenoyl-α-carbamoyl ketene-S,S-acetals has been developed. Subjected to N,N-dimethylformamide at 125°C, α-alkenoyl-α-carbamoyl ketene-S,S-acetals underwent an intramolecular aza-nucleophilic vinyl substitution reaction, a formal [5C + 1N] annulation, to give the corresponding substituted pyridine-2,4(1H,3H)-diones in high yields, whereas in the presence of Na2S·9H2O in DMF at 75°C, tandem intermolecular and intramolecular thia-nucleophilic vinyl substitution reactions, a formal [5C + 1S] annulation, occurred to produce the corresponding substituted 4H-thiopyran-4-ones in good yields.


Acknowledgements

Financial support of this research by the National Natural Science Foundation of China (grant no. 20572013 and grant no. 20872136), the Ministry of Education of China (grant no. 105061) and the Department of Science and Technology of Jilin Province (grant no. 20050309–2) is greatly acknowledged.


References


[1]   For reviews on the synthesis and application of α-oxo ketene-S,S-acetals, see: (a) Dieter R. K., Tetrahedron 1986, 42, 3029.
       (b) H. Junjappa, H. Ila, C. V. Asokan, Tetrahedron 1990, 46,  5423.
         
         
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