N-Atom Deletion in Nitrogen Heterocycles.
Angew Chem Int Ed Engl
; 60(38): 20678-20683, 2021 09 13.
Article
em En
| MEDLINE
| ID: mdl-34227207
ABSTRACT
Excising the nitrogen in secondary amines, and coupling the two residual fragments is a skeletal editing strategy that can be used to construct molecules with new skeletons, but which has been largely unexplored. Here we report a versatile method of N-atom excision from N-heterocycles. The process uses readily available N-heterocycles as substrates, and proceeds by N-sulfonylazidonation followed by the rearrangement of sulfamoyl azide intermediates, providing various cyclic products. Examples are provided of deletion of nitrogen from natural products, synthesis of chiral O-heterocycles from commercially available chiral ß-amino alcohols, formal inert C-H functionalization through a sequence of N-directed C-H functionalization and N-atom deletion reactions in which the N-atom can serve as a traceless directing group.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2021
Tipo de documento:
Article
País de afiliação:
China