期刊
TETRAHEDRON LETTERS
卷 59, 期 15, 页码 1458-1460出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.02.084
关键词
Cyclopropenone; Ring opening; Annulation; Amide; Oxazinone
资金
- JSPS, Japan [25410054, 16K05783]
- Sumitomo Foundation, Japan [130325]
The base-catalyzed [3+3]-type annulation between cyclopropenones and N-(pivaloyloxy)amides is reported. The formal insertion of a 1,3-N,O-dipole into a cyclopropenone C-C bond yields a six-membered azalactone structure. In the presence of catalytic K2CO3 at 60 degrees C in THF, the disubstituted cyclopropenone couples with benzamides, acrylamides, and a phenylacetamide to produce 2,4,5-trisubstituted 1,3-oxazin-6-ones in 23-99% yield. (C) 2018 Elsevier Ltd. All rights reserved.
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