Notes- 2-Imino-4-oxo-5-thiazolidineacetic Acid and Its Derivatives

Arakelian, A; Dunn, Horton; Grieshammer, L; Coleman, Lois

doi:10.1021/jo01073a613

Cited by 8 publications

(8 citation statements)

References 1 publication

(1 reference statement)

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“…Already, Arakelian et al, stated that maleic anhydride was less active in alcohol. [14] However, contrary to the findings of our study, Bahekar and Shinde, reported that after prolonged heating of unsymmetrical thiourea derivatives with maleic anhydride in ethanol related thiazolidine-4-one-5-acetic acids can be synthesized. [37] As a continuation of the work carried out with maleic anhydride, we also examined the reaction of N,N-didodecyl thiourea with two stereoisomeric α,β-unsaturated dicarboxylic acids such as maleic and fumaric acids under similar reaction conditions given in Table 1, entry 13.…”

Section: Resultscontrasting

confidence: 99%

“…[12,13] There are some reports of reactions of substituted thioureas with maleic acid and it is stated that the corresponding substituted thiazolidine-4-one-5-acetic acid was obtained from the reaction of N,N-dibutyl thiourea with maleic anhydride in methyl ethyl ketone with a yield of 66 %. [14] However, detailed information on the procedure or the characterization of the compound is not provided. Obushak et al, obtained substituted 4-thiazolidones by cyclization of thiouronium salts formed by 3-aryl-2-bromopropionic acid esters with N-aryl substituted thioureas.…”

Section: Introductionmentioning

confidence: 99%

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An Efficient Ni(II) Laurate Promoted Heterocyclization of Symmetrical Thioureas with Maleic Anhydride and Mechanistic Approach toward Higher Substituted Thiazolidine‐4‐one‐5‐acetic Acids

Yıldırım

Öztürk

2022

ChemistrySelect

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For the first time, readily available Ni(II) laurate catalyzed thia‐Michael addition of symmetrical N,N‐disubstituted thioureas to maleic anhydride and subsequent cyclization in toluene afforded novel thiazolidine‐4‐one‐5‐acetic acids with good yields in a short reaction time. The efficiency and low cost of the renewable, eco‐friendly laurate based homogenous Lewis acid catalyst and the fact that cyclization proceeds in a much shorter time means that this synthetic method is interesting from a green chemistry point of view. The catalyst can be reused for many times without any significant loss of activity.

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Section: Resultscontrasting

confidence: 99%

Section: Introductionmentioning

confidence: 99%

An Efficient Ni(II) Laurate Promoted Heterocyclization of Symmetrical Thioureas with Maleic Anhydride and Mechanistic Approach toward Higher Substituted Thiazolidine‐4‐one‐5‐acetic Acids

Yıldırım

Öztürk

2022

ChemistrySelect

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“…Reactions with maleic anhydride and its derivatives were investigated vigorously in 1900-2005, and this was reflected in the reviews [2,13] and papers [51][52][53][54][55]. Cycloacylation with maleic anhydride and maleamides takes place by [3+2] and [3+3] condensations.…”

Section: Reactions With Maleic Anhydride and Its Derivativesmentioning

confidence: 99%

“…In [51] 2-imino-4-oxothiazolidine-5-acetic acids and their esters and amides were obtained by the reaction of N-R 1 -N′-R 2 -thioureas 45 and fumaric (maleic) acid, diethyl maleate, and N-alkylmaleimides: 4-Oxothiazolidine-5-acetic acids 47 are also formed during the fusion of N-aryl-3-oxobutanethioamides [52] and thioureas [53] with (bromo)maleic anhydride, whereas the products from the cycloacylation of thiourea with the morpholide of maleic acid are 1,3-thiazin-4-ones 46 (53).…”

Section: Reactions With Maleic Anhydride and Its Derivativesmentioning

confidence: 99%

Cycloacylation of thioamides and their derivatives by compounds containing an activated multiple bond (review)

Britsun

Lozinskii

2007

Chem Heterocycl Comp

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The cycloacylation reactions of thioamides and their derivatives containing an activated multiple bond are analyzed and summarized.The cycloacylation of thioamides and their derivatives containing an activated multiple bond is an accessible and convenient method for the synthesis of five-and six-membered sulfur-and nitrogen-containing heterocycles -primarily 4H-1,3-thiazin-4-ones [1] and thiazolidin-4-ones [2], and also 2-thioxopiperidines [3], thiopyran-4-ones [4], and pyrimidin-4-ones [5]. Heterocyclic compounds of these types exhibit a wide spectrum of biological activity and have extensive practical applications [1,2,6].This group of reactions is also of interest from the theoretical standpoint since they make it possible to study, analyze, and predict the relationships between the reactivity of substrates containing the ambident NH─C═S group and their structure, reaction conditions, and the nature of substituents at the heteroatoms. Therefore, in spite of the fact that the first papers on this subject were published 50 of more years ago [7,8] synthetic investigations in the field are continuing to this day [9][10][11][12].Nevertheless, no reviews have been published on this subject. It should be mentioned that certain methods for the cycloacylation of thioamides by derivatives of unsaturated carboxylic acids were analyzed in reviews on the synthesis of 1,3-thiazines [1] and thiazolidin-4-ones [2, 13], reactions of N-aminoazolinethiones and N-aminoazinethiones [14], thioamides [15][16][17], and carbon suboxide [18]. However, the information on this subject in these publications has not been coordinated and is not exhaustive.New publications on the cycloacylation of thioamides, in which the range of both reagents and substrates has been extended, have appeared recently. Modern physical methods of establishing the structure of the synthesized products were used, and this made it possible to prove their structure unequivocally.For this reason we attempted to fill the gap and to analyze the information concerning the cycloacylation of acyclic and cyclic thioamides by compounds containing an activated multiple bond. This reviews covers papers not examined in [1,2,[13][14][15][16][17][18] and also papers that have appeared more recently.

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“…This phenomenon was first detected by UV spectroscopy [19] and believed to be caused by a proton transfer between nitrogen atoms (amino–imino tautomerism), however, contradictory information on the equilibrium ratio of tautomers exist [15,18,20–23]. ( E / Z )-Isomerization of the exocyclic C=N bond of the single imino form was suggested as the cause for the dynamic effect as well [24–25].…”

Section: Introductionmentioning

confidence: 99%

Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution

Pankova¹,

Golubev²,

Khlebnikov³

et al. 2016

Beilstein J. Org. Chem.

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2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones and the substituent on the exocyclic nitrogen atom governs the ratio of these tautomers. Isomers with the alkyl group in the endocyclic position can be obtained from N-methyl(ethyl)thioureas. 2D NMR spectroscopy and DFT calculations rationalize experimental results.

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Notes- 2-Imino-4-oxo-5-thiazolidineacetic Acid and Its Derivatives

Cited by 8 publications

References 1 publication

An Efficient Ni(II) Laurate Promoted Heterocyclization of Symmetrical Thioureas with Maleic Anhydride and Mechanistic Approach toward Higher Substituted Thiazolidine‐4‐one‐5‐acetic Acids

An Efficient Ni(II) Laurate Promoted Heterocyclization of Symmetrical Thioureas with Maleic Anhydride and Mechanistic Approach toward Higher Substituted Thiazolidine‐4‐one‐5‐acetic Acids

Cycloacylation of thioamides and their derivatives by compounds containing an activated multiple bond (review)

Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution

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