Synthesis and structure of 1-[ω-(3,3-dialkyldiaziridin-1-yl)alkyl]-3,3-dialkyldiaziridines

Petukhova, V. Yu.; Strelenko, Yu. À.; Махова, Нина Н.

doi:10.1007/s11172-007-0241-7

Cited by 14 publications

(4 citation statements)

References 5 publications

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“…Tetramezine [1,2‐bis(3,3‐dimethyldiaziridin‐1‐yl)ethane] was synthesized from acetone oxime p ‐toluenesulfonate and ethylendiamine according to a method described by Makhova et al50 Fast crystallization of the crude reaction product resulted in a mixture of all three stereoisomers (cf. Scheme ), whereas slow crystallization from acetone provided solely the meso isomer, which was fully characterized (cf.…”

Section: Resultsmentioning

confidence: 99%

“…Tetramezine [1,2‐bis(3,3‐dimethyldiaziridin‐1‐yl)ethane] was synthesized according to the method of Makhova et al50 22.7 g (0.10 mol) acetone oxime p ‐toluenesulfonate (prepared according to the synthesis of acetone oxime benzenesulfonate by Oxley and Short51) were dissolved in 20 ml dichloromethane. At a temperature of 10–15°C, 3.0 g ethylenediamine and 15 g triethylamine were added.…”

Section: Methodsmentioning

confidence: 99%

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Stereodynamics of tetramezine

Kamuf

Trapp

2010

Chirality

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The antidepressant drug tetramezine [1,2-bis-(3,3-dimethyldiaziridin-1-yl)ethane] consists of two bridged diaziridine moieties with four stereogenic nitrogen centers, which are stereolabile and, therefore, are prone to interconversion. The adjacent substituents at the nitrogen atoms of the diaziridines moieties exist only in an antiperiplanar conformation, which results in a coupled interconversion. Therefore, three stereoisomers exist (meso form and two enantiomeric forms), which epimerize when the diaziridine moieties are regarded as stereogenic units due to the coupled interconversion. Here, we have investigated the epimerization between the meso and enantiomeric forms by dynamic gas chromatography. Temperature-dependent measurements were performed, and reaction rate constants were determined using the unified equation of chromatography implemented in the software DCXplorer. The activation barriers of the epimerization were found to be ΔG(≠) = 100.7 kJ mol(-1) at 25°C and ΔG(≠) = 104.5 kJ mol(-1) at 37°C, respectively. The activation enthalpy and entropy were determined to be ΔH(≠) = 70.3 ± 0.4 kJ mol(-1) and ΔS(≠) = -102 ± 2 J mol(-1) K(-1) .

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Stereodynamics of tetramezine

Kamuf

Trapp

2010

Chirality

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“…Unlike diethylamine, methylamine readily reacts with tosyloxyimino derivatives 2b to give, as would be expected, diaziridine 6 (Scheme 3) [3][4][5].…”

Section: Resultsmentioning

confidence: 80%

Specific Features of Tosylation of 2-Substituted Pyrimidin-4(3H)-ones Containing a Double Bond in the α-Position of the Side Chain

et al. 2021

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The reaction of 2-(1-hydroxyimino-2-oxo-2-phenylethyl)-6-R-pyrimidin-4(3H)-ones with an excess of p-toluenesulfochloride proceeds in two stages involving consecutive oxidation of the oxygen atom of the hydroxyimino group and the oxygen atom of the amide fragment of the pyrimidine ring. The reaction of the resulting ditosylates with ethylenediamine proceeds via replacement of the sulfonyl group in the 2-position of the pyrimidine ring. The examples of 2-[1-benzoyl-2-(2-furyl)vinyl]-6-methylpyrimidin-4(3H)-one, 2-[2-(4-nitrophenyl)vinyl]-6-methylpyrimidine-4(3H)-one, and 6-methyl-2-(2-oxo-2-phenylethylthio)pyrimidin-4(3H)-one were used to consider the relationship between the structure of the substrate and the direction of the tosylation reaction.

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“…Strained diaziridine ring is inclined to ring-expansion reactions resulting in various five-eightmembered mono-and bicyclic heterocyclic structures [6,7]. In addition, some diaziridine derivatives possess the neurotropic activity [8][9][10][11]. The important properties of diaziridines are high values of formation enthalpies and low toxicity.…”

Section: Introductionmentioning

confidence: 99%

Molecular structure study of 1,2,3-trimethyldiaziridine by means of gas electron diffraction method

et al. 2018

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The molecular structure of 1,2,3-trimethyldiaziridine has been determined from the gas-phase electron diffraction data supplemented spectral and quantum chemical calculations. The configuration of studied compound incorporates trans-position of methyl groups attached to nitrogen atoms of diaziridine cycle. The following principal structural parameters were determined (r h1 bond lengths in Å, bond angles in degrees with 3σ in parentheses): r(N-C), 1.489(9); r(N-N), 1.480(15); r(C-C), 1.503(15); ∠NCN, 61.5( 9); ∠(H 3 C)CN, 124.0(15). The obtained structural parameters of 1,2,3-trimethyldiaziridine were compared with those for structural analogues. The gaseous standard enthalpy of formation of 1,2,3-trimethyldiaziridine was estimated to be 176.2 ± 5.0 kJ/mol.

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Synthesis and structure of 1-[ω-(3,3-dialkyldiaziridin-1-yl)alkyl]-3,3-dialkyldiaziridines

Cited by 14 publications

References 5 publications

Stereodynamics of tetramezine

Stereodynamics of tetramezine

Specific Features of Tosylation of 2-Substituted Pyrimidin-4(3H)-ones Containing a Double Bond in the α-Position of the Side Chain

Molecular structure study of 1,2,3-trimethyldiaziridine by means of gas electron diffraction method

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