NaOAc-Promoted [3+1+2] Annulation of O‑Pivaloyl Oximes, Aldehydes, and 2‑Methylbenzothiazole Salts: Synthesis of 1‑Azaphenothiazines

This paper presents an efficient strategy for constructing 1-azaphenothiazines through the NaOAc-promoted [3+1+2] annulation of O-pivaloyl oximes, aldehydes, and 2-methylbenzothiazole salts. The reaction is conducted in ethanol and employs oxygen as the oxidant under catalyst-free conditions. The pr...

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Veröffentlicht in:Journal of organic chemistry 2024-09, Vol.89 (18), p.13438-13449
Hauptverfasser: Liang, Baihui, Cai, Xiangya, Xu, Shengting, Huang, Jie, Deng, Haiyin, Ren, Weijie, Chen, Jiehao, Lo, Tsz Woon Benedict, Chen, Xiuwen, Zhu, Zhongzhi
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Sprache:eng
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Zusammenfassung:This paper presents an efficient strategy for constructing 1-azaphenothiazines through the NaOAc-promoted [3+1+2] annulation of O-pivaloyl oximes, aldehydes, and 2-methylbenzothiazole salts. The reaction is conducted in ethanol and employs oxygen as the oxidant under catalyst-free conditions. The process is amenable to various O-pivaloyl oximes, 2-methylbenzothiazole salts, and aldehydes, affording the target products in satisfactory yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c01590