1.
J Org Chem
; 87(14): 9011-9022, 2022 Jul 15.
Article
in English
| MEDLINE
| ID: mdl-35749377
ABSTRACT
A TEMPO-promoted method was developed for the synthesis of symmetric bis-N-Mannich bases via sequential activation of two α,α'-amino C(sp3)-H bonds of N,N-dimethylanilines under mild conditions. This methodology was further extended for monoimidation of α-amino-functionalized methylanilines to give unsymmetric N-Mannich bases in good to high yields. Several control experiments were performed, and the coupling reaction outcomes indicated that the oxoammonium (TEMPO+) species is involved in the reaction.