Neue offenkettige und cyclische α‐Nitrosaminoalkyl‐äther

Eiter, K.; Hebenbrock, Klaus-Friedrich; Kabbe, Hans‐Joachim

doi:10.1002/jlac.19727650109

Cited by 39 publications

(10 citation statements)

References 4 publications

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“…By ring-closure of 3-aminopropanol with benzaldehyde in the presence of nitrous acid, 3-nitroso-2-phenyltetrahydro-1,3-oxazine (156) was obtained in a onepot reaction. Reduction of 156 by using LiAlH 4 resulted in the N-benzyl-substituted 1,3-hydrazinoalcohol 157 [172] (Scheme 33).…”

Section: N-amination Reactions Of Aminoalcohols (Methods I and J)mentioning

confidence: 99%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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Hydrazinoalcohols are versatile di-or trifunctional compounds with wide-ranging possibilities for application in organic synthesis. Numerous methods have been devised for the preparation of this family of compounds in recent decades. This review discusses the main pathways for the synthesis of hydrazinoalcohol derivatives, including epoxide ring-openings and nucleophilic substitutions by hydrazines, addition reactions to hydroxyhydrazones, hydrazine additions to olefinic bonds, electrophilic C-and N-amination reactions, cycloadditions, reductions of N-nitroso aminoalcohols and some unique procedures. The latest developments in these fields, involving both conventional and enzymatic catalytic methods of synthetic organic chemistry, allow the highly regio-, stereo-and enantioselective preparation of hydrazinoalcohol derivatives.

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Section: N-amination Reactions Of Aminoalcohols (Methods I and J)mentioning

confidence: 99%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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“…A similar workup procedure to that used for the previous analytical samples provided 0.63 g of pale-yellow solid: IR (KBr, cm-1): 2973 (m), 2890 (m), 1460-1410 (s), 1380-1210 (s); NMR (500 MHz, CDC13): ó 5.17 Synthesis of 4-(Hydroxymethyl)-4-methyl-3-nitroso-l,3oxazolidine (6). 4-(Hydroxymethyl)-4-methyl-3-nitroso-l,3oxazolidine (6) was prepared by the method of Eiter (12) from 2-amino-2-methyl-l,3-propanediol, formaldehyde, and sodium nitrite in acetic acid to give 11.4 g (78%) of a light yellow solid: mp 43-44 °C [lit. (12) 44 °C]; IR (KBr, cm-1): 3620-3100 (s), 2950-2750 (m), 1450-1220 (s); NMR (300 MHz, CDC13):…”

Section: Methodsmentioning

confidence: 99%

An Aziridinium Ion Intermediate in the Nitrosation of a Hexetidine Model

Loeppky

Bae²

1994

Chem. Res. Toxicol.

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The nitrosation chemistry of 1,3,5-trimethyl-5-aminohexahydropyrimidine (2) has been investigated as a model for the behavior of the antimicrobial agent hexetidine (1) under similar conditions. The reaction of 2 with sodium nitrite in glacial acetic acid gives 4-methyl-4-[(methylnitrosamino)methyl]-3-nitroso-1,3-oxazolidine (4) as the major nitrosamine. This compound arises from a molecular rearrangement which proceeds through the diazotization of the primary amino group followed by intramolecular displacement of nitrogen to generate an aziridinium ion. The N-nitrosooxazolidine 4 forms from the nitrosation of an imidazolidine produced from the aziridinium ring hydrolytic opening. The N-nitrosooxazolidine 4, an isomer, 5-methyl-5-[(methylnitrosamino)methyl]-3-nitroso-1,3-oxazolidine (14), which is not formed in the nitrosation of 2, and an analog 4-methyl-4-[[(2-ethylhexyl)nitrosamino]methyl]-3-nitroso-1,3-oxazolidine (22) have been independently synthesized. The N-nitrosooxazolidine 22 which would be formed from hexetidine is not present in its nitrosation mixture, suggesting the absence of reactive aziridinium ions in that case. The dissimilar nitrosation chemistry of 2 and 1 are discussed.

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“…Finally, we want to draw attention to a little-known class of nitrosamines consisting of N-nitroso ethers [25]. Although as far as we know no such nitroso ethers have been found up to the present in foodstuffs, a cyclic representative of this class of N-nitroso com pounds has been detected now in an environmental sample [26], N-nitroso-5 -methyl-1,3-oxazolidine (NMOX; fig.…”

Section: Methodsmentioning

confidence: 99%

Daily Dietary Intakes of Nitrate, Nitrite and Volatile N-Nitrosamines in The Netherlands Using the Duplicate Portion Sampling Technique

Stephany¹,

Schuller²

1980

Oncology

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In total, 201 duplicates of all foods and drinks sampled by adult volunteers during a 24-hour sampling period have been analyzed for nitrate, nitrite and volatile N-nitrosamines. For nitrate the mean daily intake was equivalent to 179 mg of potassium nitrate per 24 h, for nitrite this intake was equivalent to 4.2 mg of sodium nitrite per 24 h. The best estimate for the total daily fraction of salivary nitrite originating from dietary nitrate has been calculated as 6.3 mol%/24 h. For N-nitrosodimethylamine the mean daily intake was 0.38 μg/24 h. The most important source of this nitrosamine contributing to the daily dietary intake was shown to be beer, which contributes 71% of the intake of an average consumer. Finally, attention has been drawn to the identification of N-nitroso-5-methyl-l,3-oxazolidine as an environmental nitrosamine present as an impurity in cutting fluids.

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Neue offenkettige und cyclische α‐Nitrosaminoalkyl‐äther

Cited by 39 publications

References 4 publications

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

An Aziridinium Ion Intermediate in the Nitrosation of a Hexetidine Model

Daily Dietary Intakes of Nitrate, Nitrite and Volatile N-Nitrosamines in The Netherlands Using the Duplicate Portion Sampling Technique

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