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Abstract 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… Click to show full abstract
Abstract 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 °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.
Keywords:
oxazin ones;
trisubstituted oxazin;
pivaloyloxy amides;
cyclopropenones pivaloyloxy;
base catalyzed;
annulation cyclopropenones
Journal Title: Tetrahedron Letters
Year Published: 2018
Link to full text (if available)
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Journal Title: Tetrahedron Letters
Year Published: 2018
Link to full text (if available)
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recommendations!