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
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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
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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
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Volumen: | 39
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Número: | 22
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Página de inicio: | 3958
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Página de fin: | 3972
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DOI: |
http://dx.doi.org/10.1080/00397910902738120 |
Título revista: | Synthetic Communications
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Título revista abreviado: | Synth. Commun.
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ISSN: | 00397911
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CODEN: | SYNCA
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CAS: | nitrosamine, 35576-91-1
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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