Phosphine-Catalyzed Annulations Based on [3+3] and [3+2] Trapping of Ketene Intermediates with Thioamides
Yu-Hao Wang, Zhen-Ni Zhao, Subarna Jyoti Kalita and Yi-Yong Huang*
*Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China,
Email: huangyy
whut.edu.cn
Y.-H. Wang, Z.-N. Zhao, S. J. Kalita, Y.-Y. Huang, Org. Lett., 2021, 23, 8147-8152.
DOI: 10.1021/acs.orglett.1c02803
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Abstract
An allenyl imide and alkynoates bearing good leaving groups are used as ketene precursors in tandem conjugate addition-elimination reactions promoted by nucleophilic phosphine catalysts. By utilizing thioamides as 1S,3N-bis-nucleophiles, [3+3] and [3+2] annulations provide rapid access to 1,3-thiazin-4-ones and 5-alkenyl thiazolones in high yields, respectively.
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Key Words
1,3-thiazin-4-ones, thiazolones, N-heterocycles, S-heterocycles
ID: J54-Y2021
