One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds.
J Org Chem
; 87(13): 8835-8840, 2022 07 01.
Article
em En
| MEDLINE
| ID: mdl-35732058
ABSTRACT
A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared in a three-step one-pot procedure starting from 5-alkoxyisoxazoles. The cyclization of 2-azabutadienes to 1-pyrrolines most likely proceeds via the 6π electrocyclization of a conjugated NH-azomethine ylide.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Azirinas
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article