Exploiting N-Centered Umpolung Reactivity of α-Iminomalonates for the Synthesis of N-Sulfenylimines and Sulfonamides.
Org Lett
; 26(8): 1629-1634, 2024 Mar 01.
Article
in En
| MEDLINE
| ID: mdl-38380999
ABSTRACT
An efficient and interesting N-centered umpolung method has been disclosed to construct beneficial S-N bonds, furnishing N-sulfenylimines, which can readily be converted into the corresponding sulfonamide derivatives in a one-pot sequential operation. N-Sulfenylimines are potent intermediates in organic synthesis, whereas sulfonamides are of major molecular interest due to their rich biological activities and wide applicability in medicinal chemistry. Owing to the simple reaction conditions and setup, this protocol displays a broad and versatile substrate scope, resulting in excellent functional group tolerability toward the synthesis of both N-sulfenylimines and sulfonamides. A density functional theory (DFT) computed and experimentally supported convenient mechanism has been proposed for this unique method.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2024
Document type:
Article
Affiliation country:
India
Country of publication:
United States