γ-Lactam synthesis from cyclobutanone via transoximation and the Beckmann rearrangement.
Org Biomol Chem
; 22(21): 4364-4368, 2024 May 29.
Article
em En
| MEDLINE
| ID: mdl-38738449
ABSTRACT
This manuscript describes the synthesis of γ-lactam from the nitrogen insertion reaction of cyclobutanones using an oxime as an aminating reagent with a catalytic amount of Brønsted acid. This method was employed with a more stable oxime reagent, which is a precursor analog of hydroxylamine derivatives with explosive properties. The reaction was tolerated by various substituted cyclobutanones and less strained five- or six-membered ketones. The obtained γ-lactam products could be transformed into γ-aminobutyric acid derivatives via ring-opening hydrolysis. The reaction mechanism is discussed from the perspective of the isotope effect, etc.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Biomol Chem
/
Org. biomol. chem
/
Organic & biomolecular chemistry
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Japão