Journal
ORGANIC LETTERS
Volume 24, Issue 1, Pages 457-461Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04179
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Funding
- Applied Basic Research Fund project of Guangdong Province of China [2019A1515110918]
- Medical Scientific Research Foundation of Guangdong Province [A2021037, A2020202]
- Key Discipline Construction Project of Guangdong Medical University [4SG21004G]
- Science and Technology Program of Guangdong Province [2019B090905011]
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A novel synthesis method has been developed for functionalized dihydrooxazines through a tandem reaction under mild conditions. The involvement of N-sulfonyl acylketenimines in [4 + 2] cycloadditions is a notable feature, and the resulting dihydrooxazines can be converted to 2-aminopyridines under basic conditions.
A tandem CuAAC/ring cleavage/[4 + 2] annulation reaction of terminal ynones, sulfonyl azides, and oximes has been developed to synthesize functionalized dihydrooxazines under mild conditions. In particular, intermediate N-sulfonyl acylketenimines are the first example of a 4p-system participating in [4 + 2] cycloadditions, and dihydrooxazines can convert to 2-aminopyridines through ring cleavage under basic conditions.
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