Regiospecific synthesis of mono-N-substituted indolopyrrolocarbazoles.
Org Lett
; 7(21): 4573-6, 2005 Oct 13.
Article
em En
| MEDLINE
| ID: mdl-16209482
ABSTRACT
[reactions see text] Two complementary and efficient strategies have been developed for the regiospecific synthesis of unsymmetrical indolopyrrolocarbazoles (IPCs) mono-N-substituted with a pentacycle. A halogen in position 2 of the intermediate bisindolylmaleimides 3a-e allows a selective Mitsunobu coupling by exploiting the increased acidity of the 2-chloro-substituted indole nitrogen. It also promotes an easier cyclization of bisindolylmaleimides 4a-e and 7b-e to IPCs. Alkylation of the 2-unsubstituted indole-3-carboxamides 2a,b and further processing to the corresponding IPCs gives access to the opposite regioisomers.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Carbazóis
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Glicosídeos
Idioma:
En
Ano de publicação:
2005
Tipo de documento:
Article