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Abstract:

A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of formaldehyde and water is reported, which gives N,N′-substituted 4-imidazolidinones when trifluoroethanol is used as the solvent. The reaction proceeds with good yields and with a wide variety of amines and isocyanides, providing an efficient new entry to these heterocycles. A preliminary study of the reaction mechanism suggests that trifluoroethanol, although acting as the solvent, is directly involved as a reagent in the reaction pathway. © 2018 The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction
Autor:Attorresi, C.I.; Bonifazi, E.L.; Ramírez, J.A.; Gola, G.F.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Ciudad Autónoma de Buenos AiresC1428EGA, Argentina
CONICET-Universidad de Buenos Aires, Unidad de Microanalisis y Metodos Fisicos Aplicados A Quimica Organica (UMYMFOR), Ciudad Universitaria, Ciudad Autónoma de Buenos AiresC1428EGA, Argentina
Palabras clave:Amines; Cyanides; Ethanol; Polyols; Heterocycles; Isocyanides; Multi-component reactions; One step synthesis; Primary amines; Reaction mechanism; Reaction pathways; Trifluoroethanol; Chemical reactions
Año:2018
Volumen:16
Número:46
Página de inicio:8944
Página de fin:8949
DOI: http://dx.doi.org/10.1039/c8ob02229a
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v16_n46_p8944_Attorresi

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Citas:

---------- APA ----------
Attorresi, C.I., Bonifazi, E.L., Ramírez, J.A. & Gola, G.F. (2018) . One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction. Organic and Biomolecular Chemistry, 16(46), 8944-8949.
http://dx.doi.org/10.1039/c8ob02229a
---------- CHICAGO ----------
Attorresi, C.I., Bonifazi, E.L., Ramírez, J.A., Gola, G.F. "One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction" . Organic and Biomolecular Chemistry 16, no. 46 (2018) : 8944-8949.
http://dx.doi.org/10.1039/c8ob02229a
---------- MLA ----------
Attorresi, C.I., Bonifazi, E.L., Ramírez, J.A., Gola, G.F. "One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction" . Organic and Biomolecular Chemistry, vol. 16, no. 46, 2018, pp. 8944-8949.
http://dx.doi.org/10.1039/c8ob02229a
---------- VANCOUVER ----------
Attorresi, C.I., Bonifazi, E.L., Ramírez, J.A., Gola, G.F. One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction. Org. Biomol. Chem. 2018;16(46):8944-8949.
http://dx.doi.org/10.1039/c8ob02229a