NIS-Promoted Selective Amino-Diazidation and Amino-Iodoazidation of O-Homoallyl Benzimidates: Synthesis of Vicinal Diazido 1,3-Oxazines and Vicinal Iodoazido 1,3-Oxazines.
J Org Chem
; 87(24): 16578-16591, 2022 12 16.
Article
em En
| MEDLINE
| ID: mdl-36450035
ABSTRACT
Amines, especially those with multi-nitrogen moieties, are widespread in natural products and biologically active compounds. Thus, the development of direct and efficient methods to introduce multiple nitrogen-containing fragments into compounds in one step is highly desirable yet challenging. Herein, we report an NIS-promoted selective amino-diazidation and amino-iodoazidation of O-homoallyl benzimidates with NaN3. By using this protocol, a variety of vicinal diazido-substituted 1,3-oxazines and vicinal iodoazido-substituted 1,3-oxazines were directly synthesized in a controllable manner. Preliminary mechanistic investigations revealed that the reaction operates through a NIS-promoted four-step cascade process. The developed method has the merits of metal-free, excellent functional group compatibility, simple operation, and mild conditions.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Oxazinas
/
Aminas
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2022
Tipo de documento:
Article