Artículo
A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
Ramirez, Maria de Los Angeles
; Ortiz, Mariela Gisela
; Salerno, Alejandra; Perillo, Isabel Amalia; Blanco, María de Las Mercedes
Fecha de publicación:
03/2012
Editorial:
Pergamon-Elsevier Science Ltd
Revista:
Tetrahedron Letters
ISSN:
0040-4039
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
In this work, we describe the synthesis of a series of 1,2,3-trisubstituted-1,4,5,6,7,8-hexahydro-1,3-diazocinium salts (1) by alkylation of the corresponding 1,2-diaryl-1,4,5,6,7,8-hexahydro-1,3-diazocines (2). Compounds 2 were obtained by ethyl polyphosphate-promoted cyclocondensation of N-aroyl-N0-arylpentamethylenediamines (3). Reaction of compounds 2 with alkyl iodides led to 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium iodides (1), a new family of cyclic amidinium salts. The best yields for the alkylation were achieved using a mixture of DCM–DMSO (10:1) as solvent. The reaction times of both, the cyclocondensation of compounds 3 and the reaction of 2 with alkyl halides, are dramatically decreased when using microwave irradiation.
Palabras clave:
Cyclic amidinium salts
,
Cyclic amidines
,
Ethyl polyphosphate
,
N-alkylation
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Articulos(OCA HOUSSAY)
Articulos de OFICINA DE COORDINACION ADMINISTRATIVA HOUSSAY
Articulos de OFICINA DE COORDINACION ADMINISTRATIVA HOUSSAY
Citación
Ramirez, Maria de Los Angeles; Ortiz, Mariela Gisela; Salerno, Alejandra; Perillo, Isabel Amalia; Blanco, María de Las Mercedes; A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 11; 3-2012; 1367-1369
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