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Abstract:

A convenient methodology, based on the addition of organolithium compounds to N-nitrosamines, was developed for the synthesis of substituted hydrazones and trialkyl hydrazines. The reaction is very sensitive to the reaction conditions, particularly the [RLi]-[nitrosamine] ratio. For molar ratios of 1-1.2, an almost quantitative conversion to the N=O bond addition products (i.e., alkylhydrazones) can be obtained in very good yields, with any remaining nitrosamine. Using greater molar ratios (in the range of 3-5), a second addition occurs, and branched trialkyl hydrazines are obtained, in good yields, with variable amounts of hydrazone remaining. Substituted hydrazines are known to have useful commercial applications and remarkable biological activities. A wide diversity of trialkyl hydrazines could be synthesized by using two different organolithiums.

Registro:

Documento: Artículo
Título:Convenient methodology for the synthesis of trialkylhydrazines
Autor:Vazquez, A.J.; Rodriguez, C.; Nudelman, N.S.
Filiación:Department of Organic Chemistry, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Palabras clave:Addition to the N=O bond; Hydrazines; Hydrazones; Nitrosamines; Organolithiums; 2,2 dicyclohexyl 1 butylidenehydrazine; 2,2 dicyclohexyl 1 methylenehydrazine; 2,2 dicyclohexyl 1 pentylidenehydrazine; 2,2 dicyclohexyl 1 propylidenehydrazine; alkylhydrazone derivative; dicyclohexylamine derivative; dicyclohexylethylhydrazone; hydrazine derivative; hydrazone derivative; n ciclohexylidenecyclohexylamine; n nitrosodicyclohexylamine; n,n dicyclohexyl na (1 butylhexyl)hydrazine; n,n dicyclohexyl na (1 butylpentyl)hydrazine; n,n dicyclohexyl na (1 ethylbutyl)hydrazine; n,n dicyclohexyl na (1 ethylhexyl)hydrazine; n,n dicyclohexyl na (1 ethylpentyl)hydrazine; n,n dicyclohexyl na (1 propylbutyl)hydrazine; n,n dicyclohexyl na (1 propylhexyl)hydrazine; n,n dicyclohexyl na pentylhydrazine; n,n dicyclohexyl na(1 propylpentyl)hydrazine; nitrosamine; organolithium compound; trialkylhydrazine derivative; unclassified drug; article; biological activity; chemical reaction; chemical structure; synthesis
Año:2009
Volumen:39
Número:22
Página de inicio:3958
Página de fin:3972
DOI: http://dx.doi.org/10.1080/00397910902738120
Título revista:Synthetic Communications
Título revista abreviado:Synth. Commun.
ISSN:00397911
CODEN:SYNCA
CAS:nitrosamine, 35576-91-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v39_n22_p3958_Vazquez

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Citas:

---------- APA ----------
Vazquez, A.J., Rodriguez, C. & Nudelman, N.S. (2009) . Convenient methodology for the synthesis of trialkylhydrazines. Synthetic Communications, 39(22), 3958-3972.
http://dx.doi.org/10.1080/00397910902738120
---------- CHICAGO ----------
Vazquez, A.J., Rodriguez, C., Nudelman, N.S. "Convenient methodology for the synthesis of trialkylhydrazines" . Synthetic Communications 39, no. 22 (2009) : 3958-3972.
http://dx.doi.org/10.1080/00397910902738120
---------- MLA ----------
Vazquez, A.J., Rodriguez, C., Nudelman, N.S. "Convenient methodology for the synthesis of trialkylhydrazines" . Synthetic Communications, vol. 39, no. 22, 2009, pp. 3958-3972.
http://dx.doi.org/10.1080/00397910902738120
---------- VANCOUVER ----------
Vazquez, A.J., Rodriguez, C., Nudelman, N.S. Convenient methodology for the synthesis of trialkylhydrazines. Synth. Commun. 2009;39(22):3958-3972.
http://dx.doi.org/10.1080/00397910902738120