Convenient methodology for the synthesis of trialkylhydrazines
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...
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2009
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v39_n22_p3958_Vazquez http://hdl.handle.net/20.500.12110/paper_00397911_v39_n22_p3958_Vazquez |
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paper:paper_00397911_v39_n22_p3958_Vazquez2023-06-08T15:03:41Z Convenient methodology for the synthesis of trialkylhydrazines 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 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. 2009 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v39_n22_p3958_Vazquez http://hdl.handle.net/20.500.12110/paper_00397911_v39_n22_p3958_Vazquez |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Convenient methodology for the synthesis of trialkylhydrazines |
| topic_facet |
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 |
| description |
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. |
| title |
Convenient methodology for the synthesis of trialkylhydrazines |
| title_short |
Convenient methodology for the synthesis of trialkylhydrazines |
| title_full |
Convenient methodology for the synthesis of trialkylhydrazines |
| title_fullStr |
Convenient methodology for the synthesis of trialkylhydrazines |
| title_full_unstemmed |
Convenient methodology for the synthesis of trialkylhydrazines |
| title_sort |
convenient methodology for the synthesis of trialkylhydrazines |
| publishDate |
2009 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v39_n22_p3958_Vazquez http://hdl.handle.net/20.500.12110/paper_00397911_v39_n22_p3958_Vazquez |
| _version_ |
1768541930149380096 |