Reaction of diketene with cyanothioacetamide: A convenient and regioselective method for the preparation of new 4(1H)-pyridone derivatives

Dotsenko, V. V.; Кривоколыско, С. Г.; Литвинов, B. П.; Чернега, А. Н.

doi:10.1007/s10593-007-0094-x

Cited by 20 publications

(8 citation statements)

References 21 publications

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“…Cyanothioacetamide reacted with compounds 3 and 4 to give compounds 12a,b . Cyanothioacetamide [42] has three nucleophile sites: the methylene carbon, the amino group and the sulfur atom. On the whole, under cyclocondensation or cycloaddition conditions, cyanothio-acetamide acts as a C,N-, C,S- or S,N- binucleophile.…”

Section: Resultsmentioning

confidence: 99%

“…By comparing the experimental cytotoxicity of the compounds reported in this study to their structures, the following structure activity relationships (SAR) are postulated: The cytotoxic activity of compounds 3 , 4 is due to the presence of the coumarin moiety and also the formation of intermolecular hydrogen bonds between the OH [53] and DNA bases.The cytotoxic activity of compounds 7a , b is due to the presence of the coumarin moiety and also the formation of intermolecular hydrogen bonds of OH and NH 2 groups with DNA bases [52]. Introducing the pyrazole carbothioamide moiety [25] also enhances the cytotoxic activity of compounds 7a , b .The cytotoxic activity of compounds 5a , b is due to the presence of the coumarin and the pyrazole carboxylic acid moieties [42] and also the formation of intermolecular hydrogen bonds between the OH and DNA bases. Compounds 7a , b demonstrated better activity compared to compounds 5a , b , probably due to the presence of the carbothioamide (S=CNH 2 ) moiety.Compounds 9a , b showed strong activity due to the presence of the coumarin and the pyridazinone rings.Compounds 15a , b and 16a showed strong and very strong activity due to the presence of the coumarin and the pyran rings.Compounds 18a showed strong activity due to the presence of the coumarin and the pyridazine rings, and also the presence of two cyano groups.…”

Section: Resultsmentioning

confidence: 99%

“…The cytotoxic activity of compounds 5a , b is due to the presence of the coumarin and the pyrazole carboxylic acid moieties [42] and also the formation of intermolecular hydrogen bonds between the OH and DNA bases. Compounds 7a , b demonstrated better activity compared to compounds 5a , b , probably due to the presence of the carbothioamide (S=CNH 2 ) moiety.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Characterization of Some New Coumarins with in Vitro Antitumor and Antioxidant Activity and High Protective Effects against DNA Damage

2016

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Abstract:Coumarins are naturally occurring oxygen heterocyclic compounds having multifarious medicinal properties, hence used as lead compounds for designing new potent analogs. The chromene butenoic acid 3 and the benzochromene butenoic acid 4 which are derived from the reaction of glyoxalic acid with 3-acetylcoumarin and 3-acetylbenzocoumarin, respectively, were reacted with different nitrogen and carbon nucleophiles to give new heterocyclic compounds. The structures of the prepared compounds were elucidated by IR, 1 H-NMR, and mass spectroscopy. Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines namely; hepatocellular carcinoma (liver) HepG2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis and Characterization of Some New Coumarins with in Vitro Antitumor and Antioxidant Activity and High Protective Effects against DNA Damage

2016

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“…The cycloacylation of cyanothioacetamide 1 with diketene can be regarded formally as recyclization. It takes place regiospecifically and is a preparative method for the synthesis of triethylammonium 3-cyano-6-methyl-4-oxo-1,4-dihydropyridine-2-thiolate 41 [36]. The latter serves as the initial reagent for subsequent reactions, including the production of thieno [2,3-b] During the reaction of cyanothioacetamide 1 and aryl(heteryl)methylene derivatives of Meldrum's acid 48 the products 49 from Michael addition were isolated [37], and their regiospecific alkylation with α-halocarbonyl compounds gave 6-alkylthio-1,2,3,4-tetrahydropyridines 50.…”

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

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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“…In our earlier work we have shown [1,2] that 3-cyanopyridine-2-thiolates react with malononitrile dimer (2-amino-1,1,3-tricyanopropene) in hot EtOH to afford 2,4-diamino-5-imino-5H-pyrido [2',3':2,3]thiopyrano [4,5-b]pyridines 1. The compounds 1a,b,c are promising reagents to prepare polyheterocyclic ensembles.…”

mentioning

confidence: 99%

Synthesis of 7-thia-1,4,6,8-tetraazabenzo[de]anthracenes

Доценко

Chigorina

Кривоколыско³

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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New polyheterocyclic ensembles of 8,9,10,11-tetrahydro-7-thia-1,4,6,8-tetraazabenzo[de]anthracenes were prepared by reaction of easily available 5Н-pyrido[2’,3’:2,3]thiopyrano[4,5-b]pyridines with Ас2О or acyl chlorides. The starting 5Н-pyrido[2’,3’:2,3]thiopyrano[4,5-b]pyridines were prepared by reaction of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with malononitrile dimer.

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Reaction of diketene with cyanothioacetamide: A convenient and regioselective method for the preparation of new 4(1H)-pyridone derivatives

Cited by 20 publications

References 21 publications

Synthesis and Characterization of Some New Coumarins with in Vitro Antitumor and Antioxidant Activity and High Protective Effects against DNA Damage

Synthesis and Characterization of Some New Coumarins with in Vitro Antitumor and Antioxidant Activity and High Protective Effects against DNA Damage

Heterocyclization of thioamides containing an active methylene group (review)

Synthesis of 7-thia-1,4,6,8-tetraazabenzo[de]anthracenes

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