N-methylimidazole promotes the reaction of homophthalic anhydride with imines.
J Org Chem
; 79(16): 7593-9, 2014 Aug 15.
Article
em En
| MEDLINE
| ID: mdl-25036978
ABSTRACT
The addition of N-methylimidazole (NMI) to the reaction of homophthalic anhydride with imines such as pyridine-3-carboxaldehyde-N-trifluoroethylimine (9) reduces the amount of elimination byproduct and improves the yield of the formal cycloadduct, tetrahydroisoquinolonic carboxylate 10. Carboxanilides of such compounds are of interest as potential antimalarial agents. A mechanism that rationalizes the role of NMI is proposed, and a gram-scale procedure for the synthesis and resolution of 10 is also described.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Anidridos Ftálicos
/
Piridinas
/
Ácidos Carboxílicos
/
Aldeídos
/
Imidazóis
/
Iminas
/
Isoquinolinas
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
Estados Unidos