A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and ß-nitrostyrenes, via an unprecedented reaction sequence.
Org Biomol Chem
; 9(22): 7780-90, 2011 Oct 26.
Article
em En
| MEDLINE
| ID: mdl-21975909
ABSTRACT
A six-step one-pot reaction was designed for synthesizing homodimeric 7-phenylindolo[3,2-a]carbazoles from 1H-indoles and ß-nitrostyrenes, in the presence of SnCl(2)·2H(2)O. The reactions proceeded under very mild conditions and the desired heterocycles were obtained in moderate to good yields. An unprecedented mechanism involving sequential indole dimerization, regioselective nucleophilic conjugate addition of the resulting 2,3'-biindole to ß-nitrostyrene and formal intramolecular [4 + 2]-cycloaddition is proposed.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Estirenos
/
Carbazóis
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Química Orgânica
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Substâncias Luminescentes
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Indóis
Idioma:
En
Ano de publicação:
2011
Tipo de documento:
Article