Synthesis of chromones and 4-hydroxyquinolines based on uncatalyzed condensations of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-alkoxy- and 2-nitrobenzoyl chlorides and related reactions.
Org Biomol Chem
; 7(9): 1931-8, 2009 May 07.
Article
em En
| MEDLINE
| ID: mdl-19590790
ABSTRACT
The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-methoxybenzoyl chlorides afforded 3,5-diketoesters which were transformed, by treatment with boron tribromide, into functionalized 2-hydroxychroman-4-ones or chromones. The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-nitrobenzoyl chlorides and subsequent reduction of the nitro group afforded functionalized 4-hydroxyquinolines. Their tautomeric equilibrium was studied by NMR spectroscopy and by computational methods.
Texto completo:
1
Bases de dados:
MEDLINE
Assunto principal:
Compostos de Trimetilsilil
/
Butadienos
/
Cromonas
/
Hidroxiquinolinas
/
Nitrobenzoatos
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2009
Tipo de documento:
Article
País de afiliação:
Alemanha