Synthesis of the thioamide derivatives of methyl vinyl ketone and their cyclization to 2,3-dihydro-4H-thiopyran-4-ones

Gros, L.; Westerlich, Sławomir; Wesołowska, Aneta; Jagodziński, T. S.

doi:10.1007/s10593-006-0067-5

Cited by 4 publications

(3 citation statements)

References 3 publications

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“…We note that the appearance of new methods [67] and the improvement of existing methods [3,[68][69][70] for the synthesis of 3-oxopropanethioamides have prompted further study of the heterocyclization of these thioamides.…”

Section: Heterocyclization Of 3-oxo-3-r-propanethioamides (R = Alk Ar)mentioning

confidence: 99%

“…The latter are dehydrated by the action of succinic anhydride with the formation of 1,2,5-oxadiazoles 131. Another case of successful intramolecular cyclization of 3-oxopropanethioamides was described in [68,69]. In the presence of boron trifluoride acetate 3-alkenyl-3-oxopropanethioamides 132 are converted into 2,3-dihydro-4H-thiopyran-4-ones 133 [69], which condense nonselectively with cinnamaldehyde with the formation of a mixture of thiopyrano[3,2-b]pyridines (total yield 35%, 135:136 ratio 3:2).…”

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

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: Heterocyclization Of 3-oxo-3-r-propanethioamides (R = Alk Ar)mentioning

confidence: 99%

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

confidence: 99%

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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“…These thioamides have four reactive centers and are ambident substrates which makes them promising starting materials for the synthesis of the different five and six-membered heterocycles thiopyran-4ones [2,3], piperidine-2-thiones [3,4], pyrroles [5], 1,2,3-thiadiazoles [6], and thiazolines [7]. These thioamides have four reactive centers and are ambident substrates which makes them promising starting materials for the synthesis of the different five and six-membered heterocycles thiopyran-4ones [2,3], piperidine-2-thiones [3,4], pyrroles [5], 1,2,3-thiadiazoles [6], and thiazolines [7].…”

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confidence: 99%