Synthesis of novel synthetic intermediates from the reaction of benzimidazole and triazole carbenes with ketenimines and their application in the construction of spiro-pyrroles.
Org Biomol Chem
; 7(23): 5010-9, 2009 Dec 07.
Article
em En
| MEDLINE
| ID: mdl-19907793
ABSTRACT
2-(2-Alkoxycarbonyl-1-arylamino-1-propenyl)benzimidazolium and 5-(2-alkoxycarbonyl-1-arylamino-1-propenyl)triazolium salts were synthesized in good yields from the reaction of benzimidazole and triazole carbenes with ketenimines. Upon treatment with a base, both salts were converted into novel 1,3-dipoles which underwent [3+2] cycloaddition reactions with electron-deficient alkynes and allenes to produce benzimidazole-spiro-pyrroles or triazole-spiro-pyrroles. This work provides novel synthons for the construction of multifunctional spiro-pyrrole derivatives that are not easy accessible by other synthetic methods and are potentially amenable to further transformations.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Pirróis
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Compostos de Espiro
/
Triazóis
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Benzimidazóis
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Iminas
/
Metano
Idioma:
En
Ano de publicação:
2009
Tipo de documento:
Article