期刊
HETEROCYCLES
卷 97, 期 1, 页码 395-408出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-18-S(T)27
关键词
-
资金
- JSPS KAKENHI [17J00349, JP 15H05485, JP 17H06092]
- Grants-in-Aid for Scientific Research [17J00349, 15H05485] Funding Source: KAKEN
We have developed a copper/manganese-mediated oxidative rearrangement of benzylamines to 4H-3,1-benzoxazines of potent interest in medicinal applications. The reaction proceeds uniquely through the initial copper/manganese-promoted intramolecular C-H amination giving benzazetidine intermediates and subsequent 4n electrocyclic ring opening/6 pi electrocyclic ring closing cascade. The key to success is the introduction of picolinamide-based N,N-bidentate directing group. The obtained benzoxazines can also be readily hydrolyzed to the corresponding 2-aminobenzyl alcohols, thus indicating that the overall transformations is regarded as the ortho-aminative rearrangement of benzylarnines to benzylic alcohols.
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