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Nizovtseva, T. V.; Komarova, T. N.; Нахманович, А. С.; Ларина, Л. И.; Лопырев, В. А.; Kalistratova, E. F.

doi:10.1023/a:1020922131002

Cited by 14 publications

(5 citation statements)

References 2 publications

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“…A cycle of investigations of malonothioamides with acetylene derivatives was undertaken in [100][101][102][103][104][105]. It was shown [100][101][102][103] that the products from the reaction of malonodithioamides 204 with aroylacetylenes 205 in the presence of an equimolar amount of HClO 4 are 2-acylmethyl-4-amino-1,3-dithiin-6-R-iminium perchlorates 206.…”

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

“…It was shown [100][101][102][103] that the products from the reaction of malonodithioamides 204 with aroylacetylenes 205 in the presence of an equimolar amount of HClO 4 are 2-acylmethyl-4-amino-1,3-dithiin-6-R-iminium perchlorates 206. With the presence of triethylamine in the reaction solution cyclization of the acetylenes with malonodithioamides was not observed [104], and the only product was cis-(benzoylvinyl) disulfide 207.…”

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

“…It was noticed that the yield of the 1,3-dithiin 211 during the reaction without the perchloric acid amounted to only 5%. On the whole it can be concluded that [5+1] cyclization of malonodithioamides in an acidic medium is realized with the participation of the S,S atoms (on account probably of the protonation of the N,N atoms) [100][101][102][103]105], whereas in a basic medium it takes place at the C, N and N,N atoms [97].…”

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

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Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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Data from the last six years on the heterocyclization of thioamides containing an active methylene group are analyzed and classified.At the present time there has been a considerable increase in the number of publications on the chemistry of thioamides, and this is explained by the value of the compounds as initial reagents for further transformations and particularly for the synthesis of various sulfur-and nitrogen-containing heterocycles [1][2][3][4][5][6][7][8]. The enormous practical significant of the latter is common knowledge -they have found application as drugs, pesticides, dyes, and preservatives.Thioamides with an active methylene group are attractive synthesis units for the production of heterocycles. These polyfunctional compounds can be represented by the formula R 3 -CH 2 CS-NR 1 R 2 (where R 1 , R 2 = H, Alk, Ar; R 3 is an electron-withdrawing group such as CN, AlkCO, ArCO, (AlkO) 2 PO, AlkSO 2 , ArSO 2 , NO 2 ). The presence of another reaction center (the methylene group) makes it possible to use them as N-С-С and S-C-C components for various condensations [1][2][3][4][5][6][7][8]. A special feature of such substrates is the ability to react both with dinucleophilic and with dielectrophilic and dipolar reagents. As a rule the products of these heterocyclizations contain functional groups, which makes it possible to achieve their modification or annelation. Such characteristics of thioamides with an active methylene group substantially increase their synthetic potential and extend the range of accessible heterosystems, while the use of modern physical methods of investigation (X-ray crystallographic analysis and 1D and 2D NMR spectroscopy) makes it possible to establish the structure of the obtained compounds unambiguously. The presence of biological activity in the products of these transformations also attracts investigators to this subject [5][6][7][8].The reason for the appearance of this review was the increasing need for generalization and classification of new information on the heterocyclization of such thioamides that had not been included in previous reviews [2][3][4][5] and also to define the trends in the study of these processes. Since one of the most important reports in this field is the review [1] we undertook an analysis of the literature that has appeared in the last six years.

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Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

Section: [5+1] Cyclocondensation Of Malonodithioamides With Acetylenementioning

confidence: 99%

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Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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“…Dithiomalondianilide 1 is actively used as an S,S-or S,N-bidentate complexing agent [35][36][37][38][39][40][41][42][43], a lubricant [44,45] and a corrosion inhibitor [46]. However, the synthetic potential of compound 1 as a reagent for heterocyclic chemistry has not yet been fully disclosed, and heterocyclization reactions were reported in only a few papers [47][48][49][50][51][52][53][54][55][56][57][58]. As cyclic disulfides, 1,2-dithiol derivatives are of special interest in biological studies since such disulfides are particularly prone to redox reactions (for the chemistry and biological activity of disulfides, see review papers [59][60][61][62][63]).…”

Section: Synthesismentioning

confidence: 99%

6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies

Dotsenko,

Bespalov,

Sinotsko

et al. 2024

IJMS

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New [1,2]dithiolo[3,4-b]pyridine-5-carboxamides were synthesized through the reaction of dithiomalondianilide (N,N′-diphenyldithiomalondiamide) with 3-aryl-2-cyanoacrylamides or via a three-component reaction involving aromatic aldehydes, cyanoacetamide and dithiomalondianilide in the presence of morpholine. The structure of 6-amino-4-(2,4-dichloro- phenyl)-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamide was confirmed using X-ray crystallography. To understand the reaction mechanism in detail, density functional theory (DFT) calculations were performed with a Grimme B97-3c composite computational scheme. The results revealed that the rate-limiting step is a cyclization process leading to the closure of the 1,4-dihydropyridine ring, with an activation barrier of 28.8 kcal/mol. Some of the dithiolo[3,4-b]pyridines exhibited moderate herbicide safening effects against 2,4-D. Additionally, ADMET (Absorption, Distribution, Metabolism, Excretion, Toxicity) parameters were calculated and molecular docking studies were performed to identify potential protein targets.

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“…Dithiomalonodiamides and, in particular, N,N'diphenyldithiomalonodiamide 1 are actively used in various chemistry fields as bidentate complexing agents [1][2][3][4][5][6], steel corrosion inhibitors [7], reagents for the Ag + extraction from chloride-containing aqueous solutions [8], and also as starting reagents for the synthesis of a number of sulfur-containing heterocyclic systems-derivatives of 1,2-dithiol [9][10][11][12][13][14], thiazole [15,16], 1,3-dithiine [17][18][19][20][21][22], [1,2]dithiolo [3,4-b]pyridine [23], 1,2,3-thiadiazole [24], thiophene [25,26], 3,5-diaminopyrazole [11,26,27], etc. (Scheme 1).…”

Section: Doi: 101134/s1070363221110037mentioning

confidence: 99%

N,N′-Diphenyldithiomalonodiamide: Structural Features, Acidic Properties, and In Silico Estimation of Biological Activity

et al. 2021

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The spectral characteristics of dithiomalondianilide ( N , N ′-diphenyldithiomalonodiamide) were studied, and the dissociation constant was determined by potentiometric titration. Quantum-chemical methods at the B3LYP-D3BJ/6-311+G (2d,p) level were used to calculate the molecular geometry and vibrational spectra of the most stable tautomeric forms of dithiomalondianilide. The bioavailability parameters were calculated, and possible protein targets were predicted by the protein ligand docking method.

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Untitled

Cited by 14 publications

References 2 publications

Heterocyclization of thioamides containing an active methylene group (review)

Heterocyclization of thioamides containing an active methylene group (review)

6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies

N,N′-Diphenyldithiomalonodiamide: Structural Features, Acidic Properties, and In Silico Estimation of Biological Activity

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