[4+2] cycloaddition reactions between 1,8-disubstituted cyclooctatetraenes and diazo dienophiles: stereoelectronic effects, anticancer properties and application to the synthesis of 7,8-substituted bicyclo[4.2.0]octa-2,4-dienes.
Chemistry
; 16(29): 8894-903, 2010 Aug 02.
Article
em En
| MEDLINE
| ID: mdl-20572168
ABSTRACT
A detailed examination of [4+2] cycloaddition reactions between 1,8-disubstituted cyclooctatetraenes and diazo compounds revealed that 4-phenyl-1,2,4-triazole-3,5-dione (PTAD) reacts to form either 2,3- or 3,4-disubstituted adducts. The product distribution can be controlled by modulating the electron density of the cyclooctatetraene. Unprecedented [4+2] cycloadditions between diisopropyl azodicarboxylate (DIAD) and 1,8-disubstituted cyclooctatetraenes are also described and further manipulation of a resulting cycloadduct uncovered a new pathway to the synthetically challenging bicyclo[4.2.0]octa-2,4-diene family. Variation of the substituents resulted in a range of compounds displaying selective action against different human tumour cell types.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Compostos Azo
/
Compostos Bicíclicos com Pontes
/
Diterpenos
/
Micro-Ondas
/
Neoplasias
/
Antineoplásicos
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article