Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 6, Pages 3702-3714Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00141
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Funding
- INSA Rouen, Rouen University
- Orleans University, CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- Lab ex IRON region Normandie (CRUNCh network) [ANR-11-LABX-0018-01]
- region Centre-Val de Loire
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An unprecedented catalytic aza-Michael addition to substituted 3-vinyl-1,2,4-triazines, as original bifunctional platforms for the domino conjugate addition inverse-electrondemand hetero-Diels-Alder/retro-Diels-Alder (ihDA/rDA) reaction, was achieved using the highly acidic triflimide as an organocatalyst. Based on the use of alkoxyamine nucleophiles, this sequence not only highlights a rare example of the catalytic aza-Michael reaction to alkenylazaarenes but also proves to be useful for the elaboration of an array of biorelevant tetrahydro[1,6]-naphthyridines.
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