4,4-Dialkyl-substituted N-Methylmorpholinium 3,5-Dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates and Some of Their Properties

Dyachenko, V. D.; Nikishin, A. A.; Chernega, Alexander N.

doi:10.1023/b:cohc.0000008259.47550.0b

Cited by 8 publications

(4 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was found that on account of presence of the bulky cyclohexyl substituent at the N atom the thioacetamide 10 reacts with halo ketones and ethyl bromoacetate with the formation not of thiazoles, as expected, but of 2-(N-cyclohexylamino)-3-cyano-4-R-thiophenes 11. Of synthetic importance is the group of reactions based on the reaction of 2-cyano-thioacetamide as the N,C,C component with derivatives of α-unsaturated ketones [23][24][25][26][27][28] and carboxylic acids [29,30]. They take place by a [3+3] cyclization mechanism and provide a general method for the production of derivatives of 3-cyanopyridine-2-thione.…”

Section: Heterocyclization Of N-r-2-cyanothioacetamides (R = H Alk Ar)mentioning

confidence: 99%

“…Chalcones [23][24][25], β-enaminocarbonyl compounds [26][27][28], and derivatives of 2-methylenecyanoacetic acid [29,30] were used as starting synthesis units. On account of the presence of the vicinal reaction groups the synthesized pyridine-2-thiones are usually employed in further transformations, including annelation to polycyclic hetero compounds [23,24,26,27,29].…”

Section: Heterocyclization Of N-r-2-cyanothioacetamides (R = H Alk Ar)mentioning

confidence: 99%

“…On account of the presence of the vicinal reaction groups the synthesized pyridine-2-thiones are usually employed in further transformations, including annelation to polycyclic hetero compounds [23,24,26,27,29].…”

Section: Heterocyclization Of N-r-2-cyanothioacetamides (R = H Alk Ar)mentioning

confidence: 99%

“…The products of the last reaction are substituted pyridine [2',3';4,5] Cyanothioacetamide and 2-benzoyl-1-(phenylamino)ethene in acetic acid were used for the synthesis of 3-cyano-6-phenylpyridine-2(1H)-thione [28]. N-Methylmorpholinium 6-oxo-1,4,5,6-tetrahydropyridinethiolates 30, produced by the condensation of cyanothioacetamide 1 with ethyl 2-cyano-3-methyl-3-R-2-propenoates 29, were transformed into 2,3,6,7-tetrahydro-5H-[1,3]thiazolo[3,2-a]pyridin-5-ones 32 [29]. 1-Amino-2,4-dicyanobuta-1,3-diene-1-thiolates and 6-amino-3-cyanopyridine-2-thiones, used as initial reagents for the synthesis of thiazoles by the Hantsch method and 6-amino-2-alkylthio-3-cyanopyridines respectively, were obtained by the cyclization of cyanothioacetamide with derivatives of ethoxymethylenecyanoacetic acid under the conditions of base catalysis [30].…”

mentioning

confidence: 99%

See 3 more Smart Citations

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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: Heterocyclization Of N-r-2-cyanothioacetamides (R = H Alk Ar)mentioning

confidence: 99%

Section: Heterocyclization Of N-r-2-cyanothioacetamides (R = H Alk Ar)mentioning

confidence: 99%

Section: Heterocyclization Of N-r-2-cyanothioacetamides (R = H Alk Ar)mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

View full text Add to dashboard Cite

show abstract

4,4‐Dialkyl‐Substituted N‐Methylmorpholinium 3,5‐Dicyano‐6‐oxo‐1,4,5,6‐tetrahydropyridine‐2‐thiolates and Some of Their Properties.

2004

View full text Add to dashboard Cite

Pyridine derivativesPyridine derivatives R 0380 4,4-Dialkyl-Substituted N-Methylmorpholinium 3,5-Dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates and Some of Their Properties. -The use of the title pyridinethiolates (IV) for the preparation of 2-alkylthio-, 2-hydrazino-and 2-acylthiotetrahydropyridines as well as thiazolopyridine (VII) is described. Moreover, a related selenazolopyridine (XII) is synthesized. -(DYACHENKO, V. D.; NIKISHIN, A. A.; CHERNEGA, A. N.; Chem. Heterocycl.

show abstract