Reaction of 3‐Oxo‐3‐R<sup>1</sup>‐N‐R<sup>2</sup>‐propanethioamides with 2‐Amino‐5‐R‐pyridines.

Britsun, V. N.; Borisevich, A. N.; Pirozhenko, V. B.; Lozinskii, M. O.

doi:10.1002/chin.200734153

Cited by 2 publications

(5 citation statements)

References 1 publication

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%

“…During study of the cyclization of N-alkyl-3-aryl-3-oxopropanethioamides 125 with 2-amino-5-R-pyridines in acetic acid their self-condensation, accompanied by the formation of 1-alkyl-5-(N-alkylaminothiocarbonyl)-4,6-diaryl-1,2-dihydropyridine-2-thiones 126 [71,72], was discovered. On the other hand the intramolecular cyclization of the isomeric N-aryl-3-oxobutanethioamides 125, which takes place in concentrated sulfuric acid [72], leads to 4-methyl-6(7)-X-1,2-dihydroquinoline-2-thiones 127.…”

Section: Self-condensation and Intramolecular Cyclization Of 3-oxopromentioning

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 3 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: Self-condensation and Intramolecular Cyclization Of 3-oxopromentioning

confidence: 99%

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

show abstract

“…On account of the strong electron-withdrawing effect of the polyfluoroalkyl groups 2-methoxy-2-R-5-methoxycarbonylmethylenethiazolidin-4-ones 4 and not thiazolidin-4-ones are formed in this reaction. Their derivatives 5 react readily with dienophiles (vinyl ethyl ether) and 1,3-dienes (isoprene and 2,3-dimethyl-1,3-butadiene), being converted into 5H-pyrano[2,3-d]thiazolines 6 and 4-oxo-1-thia-3-azaspiro [4,5] In [25,26] it was established that the thioamides 7 containing an active methylene group react smoothly with acetylenedicarboxylate ester. The reaction is selective with the formation of 2-(R 1 -methylene)-5-ethoxycarbonylmethylene-3-R 2 -1,3-thiazolidin-4-ones 8.…”

Section: Reactions With Acetylenedicarboxylic Estermentioning

confidence: 99%

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

Reaction of 3‐Oxo‐3‐R¹‐N‐R²‐propanethioamides with 2‐Amino‐5‐R‐pyridines.

Abstract: Amino-5-R-pyridines. -The reaction course in acetic acid depends on the structure of the starting thioamides to give either pyridopyrimidinethiones (III) or self-condensation products (V). -(BRITSUN, V. N.; BORISEVICH, A. N.; PIROZHENKO, V. B.; LOZINSKII, M. O.; Russ.

Cited by 2 publications

References 1 publication

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)

Contact Info

Product

Resources

About

Reaction of 3‐Oxo‐3‐R1‐N‐R2‐propanethioamides with 2‐Amino‐5‐R‐pyridines.

Abstract: Amino-5-R-pyridines. -The reaction course in acetic acid depends on the structure of the starting thioamides to give either pyridopyrimidinethiones (III) or self-condensation products (V). -(BRITSUN, V. N.; BORISEVICH, A. N.; PIROZHENKO, V. B.; LOZINSKII, M. O.; Russ.

Cited by 2 publications

References 1 publication

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)

Contact Info

Product

Resources

About

Reaction of 3‐Oxo‐3‐R¹‐N‐R²‐propanethioamides with 2‐Amino‐5‐R‐pyridines.