Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles

The synthesis of pyrrole, indole, and pyrazole fused azaheterocycles is presented. The anions of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under photostimulation by an intramolecular SRN1 process to yield fused azaheterocycles with good to excellent yields. We report on an efficient...

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Detalles Bibliográficos
Autores: Vaillard, Victoria Anahi, Buden, Maria Eugenia, Martín, Sandra Elizabeth, Rossi, Roberto Arturo
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2009
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/26110
Acceso en línea:http://hdl.handle.net/11336/26110
Access Level:acceso abierto
Palabra clave:Azaheterocycles
Intramolecular Srn1
Pyrrole
Indole
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario:The synthesis of pyrrole, indole, and pyrazole fused azaheterocycles is presented. The anions of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under photostimulation by an intramolecular SRN1 process to yield fused azaheterocycles with good to excellent yields. We report on an efficient two-step synthesis of new fused azaheterocycles derived from pyrrole, indole, and pyrazole, as well as the synthesis of their precursors. By the reaction of carboxamides (6 and 12) and pyrazolylamines (15a-b) with a base, the corresponding anion could be formed. Then, by an intramolecular photostimulated SRN1 reaction, the fused azaheterocycles were achieved (54-100%).