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Доценко, В. В.; Кривоколыско, С. Г.; Литвинов, В. П.; Чернега, А. Н.

doi:10.1023/a:1015436500899

Cited by 19 publications

(17 citation statements)

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“…The 1 H NMR spectra of selenones 3 are in good accord with the data for related 8-trioxo-3,5,7,11-tetraazatricyclo[7.3.1.0 2,7 ]tridec-2-enes [3][4][5][6][7], whose structure was demonstrated unequivocally by X-ray diffraction crystallographic analysis [5][6][7].…”

supporting

confidence: 75%

Synthesis of derivatives of 3,5,7,11-tetraaza-tricyclo[7.3.1.02,7]tridec-2-ene-8-selenone

Фролов

Dotsenko

Кривоколыско

et al. 2010

Chem Heterocycl Comp

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Selenium heterocycles display a broad spectrum of biological activity [1,2], which accounts for the interest in this area of chemistry. We have developed a method for the synthesis of a new selenium heterocyclic system, namely, 3,5,7,11-tetraazatricyclo[7.3.1.0 2,7 ]tridec-2-ene-8-selenone. Thus, we have found that 1,4-dihydropyridine-2-selenolate 1 undergoes the Mannich reaction with primary amines 2 in the presence of excess formaldehyde to give selenones 3 in 45-53% yield. O NH RNH 2 (2), HCHO 1 3 + EtOH,  2, 3 a R = 4-MeC 6 H 4 , b R = MeThe structure of selenones 3 was supported by 1 H NMR and IR spectrometry. The 1 H NMR spectra of selenones 3 are in good accord with the data for related 8-trioxo-3,5,7,11-tetraazatricyclo[7.3.1.0 2,7 ]tridec-2-enes [3][4][5][6][7], whose structure was demonstrated unequivocally by X-ray diffraction crystallographic analysis [5][6][7].The 1 H NMR spectra were taken on a Bruker Avance II 400 spectrometer at 400 MHz in DMSO-d 6 with TMS as the internal standard. The IR spectra were taken on an IKS-29 spectrophotometer for vaseline mulls.

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supporting

confidence: 75%

Synthesis of derivatives of 3,5,7,11-tetraaza-tricyclo[7.3.1.02,7]tridec-2-ene-8-selenone

Фролов

Dotsenko

Кривоколыско

et al. 2010

Chem Heterocycl Comp

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“…The aminomethylation of 6-amino-3,5-dicyano-1,4-dihydropyridine-2-thiolates with amines and formaldehyde is a successful variant of the synthesis of the derivatives of 3,5,7,11-tetraazatricyclo-[7.3.1.0 2,7 ]tridec-2-ene 99, the structure of which was confirmed by X-ray crystallographic analysis [58]. These compounds, which are representatives of a previously undescribed heterosystem, were also obtained by the reaction of the thioacetamide 1, piperidone 96, formaldehyde 97, and the amine 98.…”

Section: Mementioning

confidence: 97%

“…The multicomponent (cascade, tandem) reactions of cyanothioacetamide, the order of their stages, and the proposed mechanisms were analyzed earlier in the reviews [1, [5][6][7][8]14]. On account of the experimental convenience and technological effectiveness multicomponent reactions were developed further in [44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62]. The advantages of the condensations include the possibility of producing derivatives of 3-cyanopyridine-2-thione [44][45][46][47][48][49][50][51][52], polysubstituted thiazoles [52] and thiophenes [53], and polycyclic heterosystems containing a pyridine ring [54][55][56][57][58][59][60][61] in one pot.…”

Section: Unusual Two-component Heterocyclizations Of Cyanothioacetamidementioning

confidence: 99%

“…The structure of compounds 66 was proved both by spectroscopic methods and by alkylation at the S atom with 1,2-dibromoethane, allyl bromide, and chloroacetonitrile. An example of a multicomponent reaction is the reaction of the cyanothioacetamide 1 with arenecarbaldehydes 77 and phenacyl isothiocyanate 78, which leads to the production of 2-amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles 79 and 80 with yields of 37-54% [53]. The data from X-ray crystallographic analysis of (4R,5S/4S,5R)-2-amino-5-benzoyl-4-(2-chlorophenyl)-4,5-dihydrothiophene-3-carbonitrile indicate that the crystal contains two types of symmetrically independent molecules 79 and 80 with extremely close geometric parameters.…”

Section: Mementioning

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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“…The IR spectra of the products show bands at 3240-3180 (NH) and 1640-1620 cm -1 (pyridone C=O). The structure of thiazolo[3,2-a]pyridine 10 was supported by comparative analysis of the spectrum with the corresponding data (in particular the δ C(2)H and C(3)H values in the 1 H NMR spectra) for related compounds [23]. The 1 H NMR spectrum of 10 at 200 MHz lacks a signal for the NH group and shows a doublet at δ 3.55 ( 3 J = 6.7 Hz) and a broad doublet at δ 3.68 ppm ( 2 J = 11.8 Hz) assigned to the CH 2 I and cis-C(2)H protons, respectively.…”

mentioning

confidence: 98%