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Straightforward synthesis of 4,5-bifunctionalized 1,2-oxazinanes via Lewis acid promoted regio- and stereo-selective nucleophilic ring-opening of 3,6-dihydro-1,2-oxazine oxides

Author:
Huang, Xiu-Rong, Zhang, Yu-Mei, Wan, Ting-Biao, Zhang, Piao, Zhang, Xiu-Xiu, Wang, Fang-Ming, Xu, Defeng, Shen, Mei-Hua, Xu, Hua-Dong
Source:
Tetrahedron 2019
ISSN:
0040-4020
Subject:
Lewis acids, Lewis bases, amines, catalysts, chemical reactions, chemical structure, oxides, regioselectivity
Abstract:
Functionalized 1,2-oxazinanes are interesting and valuable heterocycles with potential applications in synthetic and medicinal chemistry. A straightforward strategy for quick access to unprecedented trans-4-hydroxyl-5-azido/cyano/amino 1,2-oxazinanes are developed: N-COR 3,6-dihydro- 1,2-oxazine oxides are prepared with ease from related dihydro- 1,2-oxazines and opened by nucleophiles TMSN3, TMSCN and aryl/alkyl amines. Appropriate Lewis acid catalysts are found playing a vital role for both reaction rate and regioselectivity. The N-COR group can be removed under mild conditions to provide highly desirable NH 1,2-oxazinanes inaccessible via previous methods.
Agid:
6454278