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Обушак, Н. Д.; Lyakhovich, M. B.; Bilaya, E. E.

doi:10.1023/a:1015394423091

Cited by 17 publications

(14 citation statements)

References 14 publications

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“…Following Nobiles [36] procedure, the 4-methylphenyldiazonium tetrachlorozincate (52) was treated with methyl acrylate to furnish the arylation product 54. [84] Although the Meerwein arylation at first appeared to work best for activated substrates, meanwhile suitable conditions have been found for the conversion of non-activated olefins too. Phenyldiazonium terafluoroborate (7) yields the dichloride 55 upon treatment with copper(II) chloride in the presence of potassium chloride (Scheme 17).…”

Section: Nitrogenmentioning

confidence: 99%

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

Heinrich

2009

Chemistry A European J

283

104

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This minireview is aimed at giving an overview of recent advances in olefin functionalisation reactions involving aryl radicals generated from arenediazonium salts. Based on the well-known Meerwein arylation, in which an aryl and a halogen substituent are coupled to an olefinic substrate, new reaction types have been developed that allow the introduction of a broad spectrum of other atoms and functional groups at the place of the original halogen atom and that are applicable to an extended range of olefinic substrates.

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Section: Nitrogenmentioning

confidence: 99%

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

Heinrich

2009

Chemistry A European J

283

104

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“…Interpretation of the Meerwein reaction mechanism [19,20] is grounded on a concept of a radical cation formation of UC as a promoting intermediate. It was described using ethylene as an example.…”

Section: Introductionmentioning

confidence: 99%

“…Certainly, an exact quantitative description of the activity of UC on the ground of above mentioned correlation can not be established, because of the complex yield dependence including a wide range of influencing factors. Nevertheless, it indicates some capability to make a viable impact on a new revision of the widely accepted [18][19][20] Meerwein reaction mechanism.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, the same barrier for the acrylate acid radical cation was calculated to be equal to 25.71 kcal/ mol. In the previous paradigm [20] the formation of the radical cation is considered to be a criterion of the reaction occurrence. This model explains a formation of different enantiomer forms of chloroarylation products by free rotation around the weakened C@C bond in the UC radical cation.…”

Section: Introductionmentioning

confidence: 99%

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About possibility of the triplet mechanism of the Meerwein reaction

Bondarchuk

Minaev

2010

Journal of Molecular Structure: THEOCHEM

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“…Esters IIa-IIr were prepared by reaction of arenediazonium bromides Ia-Ir with methyl or ethyl acrylate according to Meerwein [17]. The reactions were exothermic, and they were carried out at room temperature or on slight heating.…”

mentioning

confidence: 99%

Synthesis of Heterocycles from Arylation Products of Unsaturated Compounds: XIII. 5-R1-Benzyl-2-(R2-2-pyridylimino)thiazolidin-4-ones

2005

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Meerwein reactions of arenediazonium bromides with methyl and ethyl acrylates gave 3-aryl-2-bromopropionic acid esters which were subjected to cyclocondensation with N- (2-pyridyl)-and N-(6-methyl-2-pyridyl)thioureas to obtain 5-R 1 -benzyl-2-(R 2 -2-pyridylimino)thiazolidin-4-ones. The latter were shown to exist in solution as E isomers of the imino form. * For communication XII, see [1].The thiazolidine ring is a promising and effective structural fragment for the design of biologically active compounds [2][3][4]. Methods of synthesis of combinatorial libraries of 4-thiazolidinone derivatives have been developed [5][6][7]. In the recent time, 5-R-benzylthiazolidine-2,4-diones attract increased interest, and some compounds of this series have already been introduced into medical practice as antidiabetic agents [8][9][10][11]. By contrast, 2-imino derivatives of 4-thiazolidinone have been studied to a lesser extent, despite the possibility for introducing an additional pharmacophoric fragment into the 2-position. A probable reason is the limited set of convenient methods for the synthesis of such compounds with various substituents in both the thiazolidine ring and the imino fragment. A general procedure for the synthesis of 2-iminothiazolidin-4-ones is based on cyclocondensation of monoand disubstituted thioureas with α-halo acids and their esters [2,12]. However, the application of this procedure is limited due to the fact that the cyclization is selective only when the nitrogen atoms in thioureas are characterized by considerably different nucleophilicities [13] or when other structural factors are favorable (e.g., hydrogen bond formation) [14].5-Benzyl-2-iminothiazolidin-4-ones can be prepared by reaction of 3-aryl-2-bromopropionic acid esters with thiourea [15,16]. In the present work we made an attempt to synthesize 5-benzylthiazolidin-4-ones containing a 2-pyridylimino group in position 2. We found that methyl and ethyl 3-aryl-2-bromopropionates IIa-IIr react with N-(2-pyridyl)thioureas IIIa and IIIb to give the corresponding 5-R 1 -benzyl-2-(R 2 -2-pyridylimino)thiazolidin-4-ones IVa-IVp and Va-Ve (Scheme 1). The reactions were carried out by heating the reactants for a short time in alcohol in the presence of a base. No elimination of hydrogen bromide from esters IIa-IIr (with formation of cinnamic acid derivatives) occurred under these conditions. Compounds IVa-IVp and Va-Ve were isolated in high yields as colorless crystalline substances which were sparingly soluble in alcohol, dioxane, and DMF. It should be noted that some 2-(2-pyridylimino)thiazolidin-4-ones were found to exhibit antibacterial activity [13].Esters IIa-IIr were prepared by reaction of arenediazonium bromides Ia-Ir with methyl or ethyl acrylate according to Meerwein [17]. The reactions were exothermic, and they were carried out at room temperature or on slight heating. Compounds IIa-IIr can be distilled under reduced pressure; they were isolated as light yellow liquids or crystalline substances. N-(2-Pyridyl)thioureas IIIa and IIIb wer...

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Untitled

Cited by 17 publications

References 14 publications

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

About possibility of the triplet mechanism of the Meerwein reaction

Synthesis of Heterocycles from Arylation Products of Unsaturated Compounds: XIII. 5-R1-Benzyl-2-(R2-2-pyridylimino)thiazolidin-4-ones

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