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: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 11433caa a22011897a 4500 | ||
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| 001 | PAPER-9009 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230414182753.0 | ||
| 008 | 190411s2009 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-70350662762 | |
| 024 | 7 | |2 cas |a nitrosamine, 35576-91-1 | |
| 030 | |a SYNCA | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Vazquez, A.J. | |
| 245 | 1 | 0 | |a Convenient methodology for the synthesis of trialkylhydrazines |
| 260 | |c 2009 | ||
| 270 | 1 | 0 | |m Nudelman, N. S.; Department of Organic Chemistry, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina; email: nudelman@qo.fcen.uba.ar |
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| 504 | |a Nudelman, N.S., Schulz, H., Garćia Linares, G., Bonatti, A.E., Further insights into the chemistry of acyllithium compounds R 2 NC(O) Li: Characterization of an amide (R2NLi) adduct (R2NCHNR2(OLi)) to a formamide (R2NC(O)H) (1998) Organometallics, 17, pp. 146-150 | ||
| 504 | |a Nudelman, N.S., Garćia Linares, G., New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O) CLi(OLi)NR2) (2000) J. Org. Chem., 65, pp. 1629-1635 | ||
| 504 | |a Michejda, C.J., Schluenz, R.W., Reactions of N-nitrosamines with Grignard and lithium reagents (1973) J. Org. Chem., 38, pp. 2412-2415 | ||
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| 506 | |2 openaire | ||
| 520 | 3 | |a 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. |l eng | |
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP no. 6019 | ||
| 536 | |a Detalles de la financiación: A.V. and C.R. are grateful recipients of the National Research Council (CONICET) fellowships. The authors are indebted to the United Nations Environmental Program (Project PNUD/ARG 02/18 Subproj. B-C-53) and to CONICET (PIP no. 6019) for financial support. | ||
| 593 | |a Department of Organic Chemistry, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ADDITION TO THE N=O BOND |
| 690 | 1 | 0 | |a HYDRAZINES |
| 690 | 1 | 0 | |a HYDRAZONES |
| 690 | 1 | 0 | |a NITROSAMINES |
| 690 | 1 | 0 | |a ORGANOLITHIUMS |
| 690 | 1 | 0 | |a 2,2 DICYCLOHEXYL 1 BUTYLIDENEHYDRAZINE |
| 690 | 1 | 0 | |a 2,2 DICYCLOHEXYL 1 METHYLENEHYDRAZINE |
| 690 | 1 | 0 | |a 2,2 DICYCLOHEXYL 1 PENTYLIDENEHYDRAZINE |
| 690 | 1 | 0 | |a 2,2 DICYCLOHEXYL 1 PROPYLIDENEHYDRAZINE |
| 690 | 1 | 0 | |a ALKYLHYDRAZONE DERIVATIVE |
| 690 | 1 | 0 | |a DICYCLOHEXYLAMINE DERIVATIVE |
| 690 | 1 | 0 | |a DICYCLOHEXYLETHYLHYDRAZONE |
| 690 | 1 | 0 | |a HYDRAZINE DERIVATIVE |
| 690 | 1 | 0 | |a HYDRAZONE DERIVATIVE |
| 690 | 1 | 0 | |a N CICLOHEXYLIDENECYCLOHEXYLAMINE |
| 690 | 1 | 0 | |a N NITROSODICYCLOHEXYLAMINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA (1 BUTYLHEXYL)HYDRAZINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA (1 BUTYLPENTYL)HYDRAZINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA (1 ETHYLBUTYL)HYDRAZINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA (1 ETHYLHEXYL)HYDRAZINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA (1 ETHYLPENTYL)HYDRAZINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA (1 PROPYLBUTYL)HYDRAZINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA (1 PROPYLHEXYL)HYDRAZINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA PENTYLHYDRAZINE |
| 690 | 1 | 0 | |a N,N DICYCLOHEXYL NA(1 PROPYLPENTYL)HYDRAZINE |
| 690 | 1 | 0 | |a NITROSAMINE |
| 690 | 1 | 0 | |a ORGANOLITHIUM COMPOUND |
| 690 | 1 | 0 | |a TRIALKYLHYDRAZINE DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a BIOLOGICAL ACTIVITY |
| 690 | 1 | 0 | |a CHEMICAL REACTION |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a SYNTHESIS |
| 700 | 1 | |a Rodriguez, C. | |
| 700 | 1 | |a Nudelman, N.S. | |
| 773 | 0 | |d 2009 |g v. 39 |h pp. 3958-3972 |k n. 22 |p Synth. Commun. |x 00397911 |t Synthetic Communications | |
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| 856 | 4 | 0 | |u https://doi.org/10.1080/00397910902738120 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00397911_v39_n22_p3958_Vazquez |y Handle |
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