Reaction of 3-oxo-N-phenylbutanethioamide with 5-amino-1H-1,2,4-triazoles

Britsun, V. N.; Borisevich, A. N.; Samoilenko, L. S.; Chernega, Alexander N.; Lozinskii, M. O.

doi:10.1134/s1070428006100216

Cited by 9 publications

(6 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reactions take place both in acetic acid [71,[76][77][78][79] and without a solvent [78][79][80]. It was found [79] that the ratio of the derivatives of 4-arylaminopyrimidine and 4-pyrimidinethione depends on three factors, i.e., the basicity of the heterocycle in the initial 2-aminoazoles(azines), the nature of the substituent in the phenyl ring of the thioamides, and the protonating ability of the solvent.…”

Section: [3+3] Cyclocondensation Of 3-oxopropanethioamides With 13-dmentioning

confidence: 98%

“…Whilst the reactions of 3-oxopropanethioamides with 1,2-dinucleophiles and 1,2-and 1,3-dielectrophilic reagents were investigated earlier, recently it was shown that they can also react with nitrogen-containing 1,3-dinucleophiles of heterocyclic [71,[76][77][78][79] and acyclic [80] structures.…”

Section: [3+3] Cyclocondensation Of 3-oxopropanethioamides With 13-dmentioning

confidence: 99%

“…It was established that N-aryl-3-oxobutanethioamides 144 undergo cyclization with 2-amino-5-R-pyridines [71], 3-amino-5-R-1,2,4-triazoles [76], 2-amino-4-R-5-R-thiazoles [77], 5-amino-3-R 1 -4-R 2 -pyrazoles [78], and 5-aminotetrazole [79] to form derivatives of 4-arylaminopyrimidine 145, 148, 150, and 151 and 4-pyrimidinethione 146, 147, 149, 152, and 153 [71,[76][77][78][79]. The reactions take place both in acetic acid [71,[76][77][78][79] and without a solvent [78][79][80].…”

Section: [3+3] Cyclocondensation Of 3-oxopropanethioamides With 13-dmentioning

confidence: 99%

See 2 more Smart Citations

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: [3+3] Cyclocondensation Of 3-oxopropanethioamides With 13-dmentioning

confidence: 98%

Section: [3+3] Cyclocondensation Of 3-oxopropanethioamides With 13-dmentioning

confidence: 99%

Section: [3+3] Cyclocondensation Of 3-oxopropanethioamides With 13-dmentioning

confidence: 99%

See 1 more Smart Citation

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

show abstract

“…Since the structure of compounds 43 and 44 cannot be identified unambiguously by the data from the IR, 1 H and 13 C NMR, and mass spectra, the structure of the isomers given by the authors [42] is provisional until the results from X-ray diffraction analysis are obtained. It should be noted that in the overwhelming majority of cases the reactions of 1,2,4-triazole derivatives with electrophilic reagents take place selectively at the N-1 position of the triazole ring, as confirmed by the data from X-ray crystallographic analysis [21,22,43] …”

Section: Cyclocondensation With Derivatives Of 3-r-propiolic Acidsmentioning

confidence: 72%

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

Britsun

Lozinskii

2007

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…Figure 2 shows the atom arrangements and numbering schemes for the three compounds. The bond angles and lengths within the [1,2,4]-triazolo-[1,5-a]pyrimidine fragments are all in the regions found for published compounds [52][53][54][55][56][57][58][59] and are not further discussed. Small angles are found between the pyrimidine and triazole components of the fused [1,2,4]-triazolo-[1,5-a] pyrimidine fragments: these are 2.52(13) and 1.72 (11) Interplanar angles between the best planes through the triazolopyrimidine and the chlorophenyl rings in 1a,1b and 1c are listed in Table 1.…”

Section: Molecular Structuresmentioning

confidence: 99%

Crystal structures of two anhydrous and one hydrated 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine derivatives

Boechat

Pinheiro

Pinto

et al. 2014

Zeitschrift Für Kristallographie - Crystalline Materials

View full text Add to dashboard Cite

Crystal structures of two anhydrous and one hydrated 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine derivatives Abstract: While in both 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidines,1 [1a: aryl = 3,5dichlorophenyl; 1b: aryl = 2,4-dichlorophenyl), the strongest intermolecular interactions are N-H···N hydrogen bonds, different acceptor atoms are involved leading to different arrangement of molecules. In the case of 1a, N2A-H2A···N4B and N2B-H2B···N3A hydrogen bonds generate tetrameric units, composed of two molecules of each of the independent molecules, Mol A and Mol B. In the case of 1b, N2A-H2A···N4B and N2B-H2B···N4A hydrogen bonds generate C12 chains of alternate molecules A and B. As well as the strong N-H···N hydrogen bonds, there are also weaker π···π, C-X···π (X = Cl, F and H) and C-H···F interactions in 1a, and π···π, C-X···π (X = H and Cl) and C-H···X (X = F and N) interactions in 1b. In {[7-(4-chlorophenylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine]. (H 2 O)}, [1c(H 2 O)], chains, C 2 2 (16) of alternate molecules of 1c and water are generated from combinations of OW-HW···N and N-H···OW intermolecular hydrogen bonds: also present are π(pyrimidine)···π(chlorophenyl), C-Cl··· π(triazole) and C-F··· π(pyrimidine) interactions. Comparisons with reported [1,2,4]-triazolo-[1,5-a]pyrimidine structures clearly show variations in the N-H···N hydrogen bonding patterns and the significant influence of the type and position of substituents on the supramolecular assemblies generated.

show abstract

Reaction of 3-oxo-N-phenylbutanethioamide with 5-amino-1H-1,2,4-triazoles

Cited by 9 publications

References 8 publications

Heterocyclization of thioamides containing an active methylene group (review)

Heterocyclization of thioamides containing an active methylene group (review)

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

Crystal structures of two anhydrous and one hydrated 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine derivatives

Contact Info

Product

Resources

About