Iron-Catalyzed Denitrogenative Annulation Reactions between α-Azido Acetamides and Cyclic Ketones.
Org Lett
; 26(3): 613-618, 2024 Jan 26.
Article
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| MEDLINE
| ID: mdl-38215045
ABSTRACT
We report an FeCl2-catalyzed annulation reaction between α-azido acetamides and cyclic ketones. Two types of α,ß-unsaturated γ-lactam products can be obtained, depending on the reaction conditions. When α-azido acetamides were reacted with cyclohexanone, 8-amino-5,6,7,8-tetrahydro-1H-indol-2(4H)-ones were obtained when a primary amine was present in the reaction system; conducting the reaction in the presence of 2-aminobenzenesulfonic acid, on the contrary, resulted in the formation of 5,6-dihydro-1H-indol-2(4H)-ones. Cycloheptanone and cyclooctanone reacted in the same way as cyclohexanone. The reactions proceed via the intermediacy of 2-iminoacetamides, which are formed by FeCl2-facilitated dinitrogenation of α-azido acetamides. These reactions constitute a new strategy for expanding the synthetic dimensions of organic azides.
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1
Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2024
Tipo del documento:
Article
País de afiliación:
China