Zur Darstellung von Imidazolidin-thionen-(4) und Imidazolin-(3)-thionen-(5)

Asinger, Friedrich; Schäfer, Wolfgang; Meisel, Hans; Kersten, H.; Saus, A.

doi:10.1007/bf00899950

Cited by 8 publications

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“…[53][54][55][56][57] This reaction course was explained by cyclo-condensation of the corresponding ketone released from α-aminonitrile together with the formed α-aminothioamide (Scheme 9).…”

Section: Methodsmentioning

confidence: 99%

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2-Amino-2-alkyl(aryl)propanenitriles as key building blocks for the synthesis of five-membered heterocycles

Drabina¹,

Sedlák²

2012

Arkivoc

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This review article summarizes recent developments and trends in the application of 2-amino-2-alkyl(aryl)propanenitriles as precursors for the syntheses of heterocyclic systems such as imidazole derivatives, oxazoles, isothiazoles and 1,3,2-diazaphospholidines. Also described are less usual examples of applications in which they and their analogies react as monofunctional precursors, or where they have been used as sources of a nitrile carbon atom, or as catalysts or initiators. Their chemical and/or biological properties and potential applications are discussed, along with those of the derived heterocycles.

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Section: Methodsmentioning

confidence: 99%

“…[53][54][55][56][57] A particular case of hydrolysis of 2,2,5,5-tetramethylimidazoline-4-thione gave 2-amino-2-methylthiopropanamide (Scheme 11). …”

Section: Scheme 10mentioning

confidence: 99%

2-Amino-2-alkyl(aryl)propanenitriles as key building blocks for the synthesis of five-membered heterocycles

Drabina¹,

Sedlák²

2012

Arkivoc

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“…This compound was produced through the acid hydrolysis of 2,2,5,5-tetramethylimidazolidin-4-thione (TMIT) . Asinger et al also described the synthesis of 2,2,5-trisubstituted-imidazolidin-4-thiones by reacting different α-aminothioamides (not produced as just described) with various aldehydes . Therefore, it was thought that ATA 1 could be condensed with various ketones to produce a variety of desired 2,2,5,5-tetrasubstituted-imidazolidin-4-thiones containing different substituents at the 2- and 5-positions.…”

Section: Introductionmentioning

confidence: 99%

“…9 Asinger et al also described the synthesis of 2,2,5-trisubstituted-imidazolidin-4-thiones by reacting different R-aminothioamides (not produced as just described) with various aldehydes. 10 Therefore, it was thought that ATA 1 could be condensed with various ketones to produce a variety of desired 2,2,5,5tetrasubstituted-imidazolidin-4-thiones containing different substituents at the 2-and 5-positions. This method proved successful, resulting in the synthesis of a series of tetrasubstituted-imidazolidin-4-thiones (Scheme 1), which could be oxidized to their corresponding 2,2,5,5-tetrasubstituted-imidazolidin-4-one analogues.…”

Section: Introductionmentioning

confidence: 99%

A Facile Synthetic Approach to Imidazolidinone Biocides

and

Worley

1999

Ind. Eng. Chem. Res.

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A synthetic route has been developed for the production of novel N-halamine disinfectants. These compounds are derivatives of 1,3-dichloro-2,2,5,5-tetramethylimidazolidin-4-one (DC). The synthetic route chosen consists of producing a 2,2,5,5-tetrasubstituted-imidazolidin-4-thione with identical substituents at the 2- and 5-positions, followed by hydrolysis of the cyclic thione to the corresponding acyclic aminothioamide, condensation with a ketone resulting in the formation of a 2,2,5,5-tetrasubstituted-imidazolidin-4-thione having different substituents at the 2- and 5-positions, oxidation to the corresponding 2,2,5,5-tetrasubstituted-imidazolidin-4-one, and finally, chlorination to the desired N-halamine derivative. These derivatives are more nonpolar than is DC, and thereby may possess more antimicrobial activity against microorganisms containing cell membranes of considerable lipophilicity than does DC. Preliminary results presented in this work show that these new derivatives are bactericidal, with some more so than is DC against Staphylococcus aureus. Potential applications may exist for these compounds in the disinfection of nonpolar media such as oils, paints, and lubricants as well as for aqueous solutions of organisms containing lipophilic cell membranes.

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“…and 2-amino-3-phenylthionpropionamide (10; R1 = PhCH2, R? = H) were prepared by modifications (to be published later) of methods in the literature (31,32). They were stored as the stable hydrochlorides.…”

Section: ~T R~d ~~mentioning

confidence: 99%

Basicity of the thionamide group of α-aminothionamides. Attenuation of electrostatic effects by solvation

Paventi¹,

Heirtzler²,

Edward³

1986

Can. J. Chem.

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. 64,23 10 (1986). The first dissociation constants pK1 of four diprotonated cx-aminothionamides, determined spectrophotometrically, are between -8.1 to -8.8; the second dissociation constants pK2, of three of these compounds, determined titrimetrically, are between 7.3 and 7.7. Both pK1 and pK2 values are close to those calculated from current electrostatic theory for equilibria in solutions of zero ionic strength, in spite of the fact that data for pK1 values were obtained in solutions of high ionic strength. Results indicate a much larger effect of the charged ammonium group on the basicity of the thionamide group than on the basicity of the amide group. A possible explanation based on the greater hydration of the protonated amide group is advanced. MARTINO PAVENTI, FENTON HEIRTZLER et JOHN T. EDWARD. Can. J. Chem. 64, 2310Chem. 64, (1986. Utilisant des mCthodes spectrophotomCtriques on a determine les premieres constantes de dissociation (pK,) de quatre a-aminothioamides diprotones; comme Ctant entre -8,l et -8,8; faisant appel B des mCthodes titrimetriques, on a aussi determink les deuxikmes constantes de dissociation (pK2) de trois de ces composks comme etant entre 7,3 et 7,7. Les valeurs tant des pK1 que des pK2 sont proches des valeurs calculies a partir de la theorie ilectrostatique actuelle sur les Cquilibres dans des solutions de force ionique Cgale a zero, mCme si les donnees relatives aux valeurs de pKl sont obtenues dans des solutions de forces ioniques ClevCes. Les risultats indiquent que le groupement ammonium charge provoque un effet beaucoup plus important sur la basicit6 du groupement thionamide que sur la basicite du groupement amide. On propose une explication plausible qui est bas& sur une plus grande hydratation du groupement amide proton-6.[Traduit par la revue]Starting more than 60 years ago with Bjerruln ( I ) , a long succession of investigations has elaborated an electrostatic theory of substitutent effects which is gradually winning general acceptance (2-9). However, the electrostatic effect can be profoundly altered by the presence of a solvent, and although "emphasis has shifted from continuum electrostatics to interactions between specific functionalities in the ions and appropriate sites in a few solvent molecules" (lo), a discontinuous solvation model (1 1) of quantitative (as opposed to qualitative) predictive power has been slow to emerge.The older continuum solvent model was applied to electrostatic effects by Kirkwood and Westheimer (4) in 1938. As an example, we may consider the fact that the dissociation constant K2 of monoprotonated glycine 2 would be expected to be higher than KAH of the parent acid, acetic acid, because the substituted acetate ion 3 is stabilized by electrostatic interaction between NH3+ and the negatively charged carboxylate group.' On the other hand, further dissociation of 3 should be made more difficult than the dissociation of the parent methylammonium ion (KBH+) by the same electrostatic stabilization, the substituent now being C 0 2 -. Classic...

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Zur Darstellung von Imidazolidin-thionen-(4) und Imidazolin-(3)-thionen-(5)

Cited by 8 publications

References 0 publications

2-Amino-2-alkyl(aryl)propanenitriles as key building blocks for the synthesis of five-membered heterocycles

2-Amino-2-alkyl(aryl)propanenitriles as key building blocks for the synthesis of five-membered heterocycles

A Facile Synthetic Approach to Imidazolidinone Biocides

Basicity of the thionamide group of α-aminothionamides. Attenuation of electrostatic effects by solvation

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