Synthesis of gem-dibromo 1,3-oxazines by NBS-mediated electrophilic cyclization of propargylic amides.
Org Biomol Chem
; 21(22): 4578-4582, 2023 Jun 07.
Article
em En
| MEDLINE
| ID: mdl-37195169
ABSTRACT
We present a highly efficient and practical method for synthesizing gem-dibromo 1,3-oxazines through 6-endo-dig cyclization of propargylic amides, using N-bromosuccinimide (NBS) as an electrophilic source. The metal-free reaction can be conducted under mild conditions with good functional group compatibility, delivering excellent yields of the desired products. Mechanistic studies suggest that the reaction proceeds via a double electrophilic attack by NBS on the propargylic amide substrate.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2023
Tipo de documento:
Article