Diversity-oriented synthesis of 1-hydroxy-2,4-benzodioates by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy- and 3-silyloxy-2-alkoxycarbonyl-2-en-1-ones.
Org Biomol Chem
; 7(10): 2182-6, 2009 May 21.
Article
em En
| MEDLINE
| ID: mdl-19421458
ABSTRACT
1-Hydroxy-3,5-dimethyl-2,4-benzodioates (4-hydroxyisophthalates) were prepared by [3+3] cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 3-ethoxycarbonyl-4-trimethylsilyloxy-3-penten-2-one which is synthesized from (symmetrical) ethyl 2-acetylacetoacetate. The [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy-2-alkoxycarbonyl-2-en-1-ones, readily available by reaction of beta-ketoesters with trialkyl orthoformiates, provide a convenient and regioselective approach to a great variety of 3-substituted 1-hydroxy-2,4-benzodioates that are not readily available by other methods.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Butadienos
/
Catálise
/
Álcoois
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2009
Tipo de documento:
Article
País de afiliação:
Alemanha