Method of producing α,ω -bis-(1,5,3-dithiazepinan-3-yl)alkanes

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and specifically to a method of producing α,ω-bis-(1,5,3-dithiazepinan-3-yl)-alkanes of general formula (1):

n=1-8, which involves reaction of α,ω-alkanediamines of general formula H2N-CH2-(CH2)n-NH2, where n=1-8, with tert-N-butyl-1,5,3-dithiazepinane in chloroform in the presence of a SmCl3·6H2O catalyst with molar ratio α,ω-alkanediamine:tert-N-butyl-1,5,3-dithiazepinane:SmCl3·6H2O = 10:20:(0.3-0.7) at room temperature (about 20°C) for 2.5-3.5 hours.

EFFECT: method of obtaining novel α,ω-bis-(1,5,3-dithiazepinan-3-yl)-alkanes which can be used as antibacterial, antifungual and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special reagents for inhibiting bacterial activity in different process media (from light industry to oil industry).

1 cl, 1 tbl, 1 ex

 

The present invention relates to organic chemistry, specifically to a method for producing α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1):

Nitrogen and sulfur-containing heterocycles are known as antibacterial, antifungal, and antiviral agents (M.R. Stillings, Welbourn A.P., D.J. Walter Substituted 1,3,4-thiadiazoles with anticonvulsant activity // Med. Chem. 1986; 29. P.2280-2284; Kidwai, M., N. Negi, Director S.R. Cyclothiomethylation of arge hydrazines with formaldehyde // Acta Pharma. 1995. 45. P.511; Tyukavkina H.A., Zurabyan SE, Beloborodov V.L. and other Organic chemicals. M.: bustard, 2008, p.66-67). They are promising as catalysts, biologically active agents, selective sorbents and extractants precious metals [Deutsche Gold - und Silber-Scheideanstalt vormals Roessler. F.P. 1,341,792/1963 (Chem. Abs., 1964, 60, 5528d)], special reagents to inhibit bacterial activity in different technical environments (from light industry to oil) (Dzhemilev sea level, Aleev R.S., galinova US, Kunakova W., Khafizova S.R., Kovtunenko SV, Kalimullin A.A. Andrianov V.M., Ismagilov FR, Gafiatullin P.P. Tool to inhibit the growth of sulfate reducing bacteria. Pat. Of the Russian Federation No. 2160233, 2000; Dzhemilev sea level, Aleev R.S., galinova US, Kunakova W., Khafizova S.R. Means to inhibit the growth of sulfate reducing bacteria. Pat. Of the Russian Federation No. 2206726, 2003).

The known method [Fr. Pat. 1,341,792/1963 (Chem. Abs., 1964, 60, 5528d)] obtain 5-[2-[1,3,5 di is asinan-5-yl]ethyl]1,3,5-diazinane (2), the interaction of sodium hydrosulfide with Ethylenediamine and formaldehyde according to the scheme:

The known method does not allow to obtain α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

The known method (Seraphita, Vremeto, Lphraw, Tavakilov, Grenadilla, Rvenue, Aagrawal, Usmjerili. Multicomponent condensation of aliphatic amines with formaldehyde and hydrogen sulfide. WPI. An. Ser. chem., 2005, 2, 423) obtain 5-[2-[1,3,5-diazinon-5-yl]ethyl]1,3,5-diazinane (2) three-component condensation of hydrogen sulfide with formaldehyde and Ethylenediamine, taken in a molar ratio of 1:6:4, respectively, at a temperature of 80°C With a yield of 44%.

The known method does not technological, as it implies the use of gaseous and highly toxic hydrogen sulfide, which at high concentrations, has no smell, but even once its inhalation may cause instant death. In addition, the known method cannot be obtained from α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

Thus, the literature contains no information about selective receipt of α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

We propose a new method of obtaining α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

The essence of the method zaklyuche is camping in the interaction of α,ω-alkadiene General formula H 2N-CH2-(CH2)n-NH2where n=1-8, with tert-N-butyl-1,5,3-diazepinone in the presence of a catalyst SmCl3·6H2O, taken in a molar ratio of α,ω-alindeman:tert-N-butyl-1,5,3-diazepine:SmCl3·6H2O=10:20:(0,3-0,7), preferably 10:20:0,5. The mixture is stirred for 2.5-3.5 hours at a temperature of 20 ° C and atmospheric pressure in chloroform (CHCl3) as solvent. The output of the α,ω-bis-(1,5,3-diazepine-3-yl)alkanes (1) is 53-71%. The reaction proceeds according to the scheme:

α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1) are formed only with the participation of tert-N-butyl-1,5,3-diazepinone and α,ω-alkadienes taken in a molar ratio of 20:10 (stoichiometric amount). When a different ratio of initial reagents reduces the yield of the target product (1). Without catalyst, the reaction proceeds with output not exceeding 20%.

The conduct of a specified reaction in the presence of a catalyst SmCl3·6H2O more than 7 mol.% does not lead to a significant increase in the yield of the target product (1). The use of catalyst SmCl3·6H2O less than 3 mol.% reduces output (1), which is connected, possibly, with a reduction of catalytically active sites in the reaction mass. The reaction was carried out at a temperature of 20°C. At temperatures above 20°C (e.g., 60°C) increase energy costs, and at a temperature below 20°is (for example, 0°C) decreases the reaction rate. The experiments were carried out in chloroform, as well dissolve the target products.

Significant differences of the proposed method:

In the known method the reaction proceeds with participation as a source of reactant gaseous hydrogen sulfide at a temperature of 80°C with the formation of six-membered N,S-containing heterocycles, namely, 5-[2-[1,3,5-diazinon-5-yl]ethyl]1,3,5-diazinane (2). The known method does not allow the individual α,ω-bis-(1,5,3-diazepine-3-yl)alkanes (1) the General formula (1).

In the proposed method, the reaction proceeds with participation as a source of reagent tert-N-butyl-1,5,3-diazepinone at a temperature of 20°C under the action of catalyst SmCl3·6H2O. In contrast to the known proposed method allows you to obtain an individual α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1), the synthesis of which are not described in literature.

The method is illustrated by examples:

Example 1. In the vessel Slanka mounted on a magnetic stirrer, an argon atmosphere at a temperature of ~20°C is placed 10 mmol of 1,2-academia and 0.5 mmol SmCl3·6H2O, then add 20 mmol of tert-N-butyl-1,5,3-diazepinone in 10 ml of chloroform. The reaction mixture is stirred at a temperature of ~20°C for 3 hours, add 2 ml of H2O and extracted with chloroform. Chloroform fraction purified column chromatography is and SiO 2allocate α,ω-bis-(1,5,3-diazepine-3-yl)ethane with the release of 65%.

Other examples of the method are given in table 1.

Table 1
№ № p/pSource α,ω-diamineThe ratio of α,ω-diamine:tert-N-butyl-1,5,3-diazepine: SmCl3·6H2O mmolReaction time, hoursOutput (1), %
11,2-amandemen10:20:0.5365
2-"-10:20:0.3353
3-"-10:20:0.7371
4-"-10:20:0.52.560
5-"-10:20:0.5 3.569
61,3-propandiamine10:20:0.5368
71,4-butanediamine10:20:0.5366
81,5-pentanediamine10: 20:0.5364
91,6-hexanediamine10:20:0.5362
101,7-heptadien10: 20:0.5359
111,8-octanediamine10:20:0.5357
121,9-enantiomer10:20:0.5355

All experiments Prov the Dili in chloroform at room temperature (~20ºC).

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)ethane1:

1(Control reaction was carried out by TLC on Silufol plates W-254, showed pairs I2. For column chromatography was used silica gel KSK (100-200 μm). The melting point is defined on the device OOC 80/2617. The NMR spectra of 1D (1H,13C) and 2D (COSY, NOESY, HSQC, NMVS) removed spectrometer Bruker Avance 400 (100.62 MHz for13And 400.13 MHz for1N) by standard methods (Bruker, internal standard Me4Si, solvent CDCl3. Mass high resolution spectra obtained on the instrument MALDI TOF/TOF AUTOFLEX III (Bruker).)

TPL 144-145°C. Eluent hexane:ethyl acetate (4:3), Rf0.5. An NMR spectrum1N, δ, ppm: 2.86 (USS, 4H, CH2(8, 9)); 3.06 (USS, 8H, CH2(6, 6', 7, 7')); 4.20 (USS, 8H, CH2(2, 2', 4, 4'). An NMR spectrum13C, δ, ppm: 35,81 (t, C-6, C-6', C-7, C-7'), 47.77 (t, C-8, C-9), 59.71 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 297.333 [M+H]+. C10H20N2S4. M 296.543.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-proppa:

TPL 73-74°C. Eluent hexane:ethyl acetate (4:3), Rf0.5. An NMR spectrum1H, δ, ppm: 1.77 (m, 2H, CH2(9)); 2.74 (m, 4H, CH2(8, 10)); 3.04 (USS, 8H, CH2(6, 6', 7, 7')); 4.15 (USS, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: at 24.48 (t, C-9), 35.88 (t, C-6, C-6', C-7, C-7'), 48.67 (t, C-8, C-10), 59.54 (t, C-2, C-2', C-4, C-4').

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The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-butane:

TPL 122-123º. Eluent hexane:ethyl acetate (4:3), Rf0.5. An NMR spectrum1H, δ, ppm: 1.48 (USS, 4H, CH2(9, 10)); 2.68 (USS, 4H, CH2(8, 11)); 3.03 (USS, 8H, CH2(6, 6', 7, 7')); 4.15 (USS, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: 24.68 (t, C-9, C-10), 35.90 (t, C-6, C-6', C-7, C-7'), 50.64 (t, C-8, C-11), 59.51 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 347.287 [M+Na]+. C12H24N2S4. M 324.596.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-pentane:

Eluent hexane:ethyl acetate (4:3), Rf0.5. An NMR spectrum1N, δ, ppm: 1.35 (m, 2H, CH2(10)); 1.48 (m, 4H, CH2(9, 11)); 2.67 (t, J=7.2 Hz, 4H, CH2(8, 12)); 3.04 (USS, 8H, CH2(6, 6', 7, 7')); 4.16 (USS, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: 25.01 (t, C-10), 26.78 (t, C-9, C-11), 35.94 (t, C-6, C-6', C-7, C-7'), 50.86 (t, C-8, C-12), 59.51 (t, C-2, C-2', C-4, C-4').

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-hexane:

TPL 84-86°C. Eluent hexane:ethyl acetate (4:3), Rf0.45. An NMR spectrum1N, δ, ppm: 1.35 (USS, 4H, CH2(10, 11)); 1.46 (USS, 4H, CH2(9, 12)); 2.67 (m, 4H, CH2(8, 13)); 3.05 (d, J=10.4 Hz, 8H, CH2(6, 6', 7, 7')); 4.17 (d, J=10.4 Hz, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: 26.96 (t, C-10, C-11); 27.16 (t, C-9, C-12); 35.93 (t, C-6, C-6', C-7, C-7'), 50.91 (t, C-8, C-13), 59.56 (t, C-, C-2', C-4, C-4'). MALDI TOF, m/z: 375.241 [M+Na]+. C14H28N2S4. M 352.649.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-heptane:

TPL 69-70°C. Eluent hexane:ethyl acetate (4:3), Rf0.45. An NMR spectrum1N, δ, ppm: 1.33 (USS, 8H, CH2(9, 10, 12, 13)); 1.45 (USS, 2H, CH2(11)); 2.66 (t, J=8.8 Hz, 4H, CH2(8, 14)); 3.05 (USS, 8H, CH2(6, 6', 7, 7')); 4.17 (USS, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: 26.97 (t, C-10, C-12), 27.27 (t, C-9, C-13), 29.30 (t, C-11), 35.94 (t, C-6, C-6', C-7, C-7'), 50.98 (t, C-8, C-14), 59.56 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 389.271 [M+Na]+. C15H30N2S4. M 366.676.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-octane:

TPL 70-71°C. Eluent hexane:ethyl acetate (4:3), Rf0.45. An NMR spectrum1H, δ, ppm: 1.32 (USS, 8H, CH2(10,11, 12,13)); 1.58 (USS, 4H, CH2(9,14)); 2.67 (t, J=7.2 Hz, 4H, CH2(8, 15)); 3.06 (USS, 8H, CH2(6, 6', 7, 7')); 4.18 (USS, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: 27.01 (t, C-10, C-13), 27.27 (t, C-9, C-14), 29.40 (t, C-11, C-12), 35.95 (t, C-6, C-6', C-7, C-7'), at 51.03 (t, C-8, C-15), 59.58 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 381.319 [M+H]+. C16H32N2S4. M 380.702.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-nonane:

TPL 60-62°C. Eluent hexane:ethyl acetate (4:3), Rf0.45. An NMR spectrum1N, δ, ppm: 1.31 (at s, 8H, CH2(9, 10, 14, 15)); 1.44 (m, 4H, CH2(11, 13)); 1.58 (USS, 2H, CH2(12)); 2.67 (t, J=7.2 Hz, 4H, CH2(8, 16)); 3.06 (USS, 8H, CH2(6, 6', 7, 7')); 4.18 (USS, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: 27.03 (t, C-10, C-14), 27.31 (t, C-9, C-15), 29.41 (t, C-11, C-13), 29.51 (t, C-12), 35.95 (t, C-6, C-6', C-7, C-7'), 51.05 (t, C-8, C-16), 59.58 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 417.258 [M+Na]+. C17H34N2S4. M 394.729.

The method of obtaining α,ω-bis-(1,5,3-diazepine-3-yl)alkanes total
formula (1):

characterized in that the α,ω-alkadiene General formula H2N-CH2-(CH2)n-NH2where n=1-8, is subjected to the interaction with tert-N-butyl-1,5,3-diazepinone in chloroform in the presence of a catalyst SmCl3·6H2O when the molar ratio of α,ω-alindeman: tert-N-butyl-1,5,3-diazepine: SmCl3·6H2O=10:20:(0,3-0,7) under room temperature (~20°C) temperature for 2.5 to 3.5 hours



 

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FIELD: chemistry.

SUBSTANCE: invention relates to 3-aza-bicyclo[3.3.0]octane derivatives of formula , where R1 and R2 are hydrogen, C1-4alkyl or fluorine; R3 is a phenyl which is unsubstituted, mono- or disubstituted, where the substitutes are independently selected from a group comprising C1-4alkyl, C1-4alkoxy group, trifluoromethyl, trifluoromethoxy group and halogen; 2,3-dihydrobenzofuranyl; 2,3-dihydrobenzo[1,4]dioxynyl; or isoxazolyl, pyridyl, indazolyl, benzofuranyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, pyrrolo[2,1b]thiazolyl, imidazo[ 1,2-a]pyridinyl or imidazo[2,1-b]thiazolyl, where said groups are unsubstituted, mono- or disubstituted, where the substitutes are independently selected from a group comprising C1-4alkyl, C1-4alkoxy group, halogen and trifluoromethyl; A is or ; R4 is C1-4alkyl or -NR6R7; R6 is hydrogen or C1-4alkyl; R7 is hydrogen or C1-4alkyl; and D is a phenyl which is unsubstituted, mono- or disubstituted, where the substitutes are independently selected from a group comprising C1-4alkyl, C1-4alkoxy group, trifluoromethyl and halogen; or a pharmaceutically acceptable salt of such a compound. 3-aza-bicyclo[3.3.0]octane derivatives or a pharmaceutically acceptable salt thereof are used as a medicinal agent having the activity of orexin receptor antagonists.

EFFECT: novel 3-aza-bicyclo[3,3,0]octane derivatives as nonpeptide antagonists of human orexin receptors.

9 cl, 1 tbl, 85 ex

FIELD: chemistry.

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51 cl, 1 tbl, 132 ex

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining α,ω-bis-(1,5,3-dithiazepinan-3-yl)-alkanes, which can be applied as antibacterial, antifungal and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media (from light industry to oil). Essence of method lies in interaction of α,ω-alkanediamine with 1,3,6-oxadithiapinane in presence of catalyst SmCl3·6H2O with mole ratio α,ω-alkanediamine : 1,3,6-oxadithiapinane : SmCl3·6H2O=10:20:(0.3-0.7) at temperature ~20°C and atmospheric pressure for 2.5-3.5 h. Output of α,ω-bis-(1,5,3-dithiazepinan-3-yl)-alkanes (1) constitutes 72-85%.

EFFECT: increase of compound application efficiency.

1 tbl, 1 ex

FIELD: chemistry.

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15 cl, 77 dwg, 10 tbl, 13 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new substituted heteroaryl derivatives of general formula I: , wherein: A means N, CR7-10, with A at the most twice meaning N; W means O, S or NR4, the values B, C, R7-10 are presented in clause 1 of the patent claim. The method for preparing the compound I is described.

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16 cl, 2 tbl, 307 ex

FIELD: chemistry.

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7 cl, 4 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing mono-(di-, tetra-)methyl-1,2-bis-(1,3,5-dithiazinan-5-yl)ethanes of general formula (1-3): , (1) R1=CH3, R2, R3, R4=H (2) R1, R3=CH3, R2, R4=H (3) R1, R2, R3, R4=CH3, which involves reaction of hydrogen sulphide-saturated aqueous solution of (37%) formaldehyde and acetaldehyde with 1,2-diaminoethane with molar ratio of initial reagents 1,2-diaminoethane: formaldehyde: acetaldehyde: hydrogen sulphide equal to 10:50:10:40 to obtain (1), 10:40:20:40 to obtain (2), 10:20:40:40 to obtain (3), at temperature 40°C and atmospheric pressure for 2.5-3.5 hours.

EFFECT: method of obtaining novel compounds which can be used as selective sorbents and extraction agents of precious metals, agents for protecting leather, fur and textile from biodeterioration, biologically active substances with respect to different microorganisms and sulphate-reducing bacteria.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 1,2-bis-(2,4,6-trialkyl-1,3,5-dithiazinan-5-yl)ethanes of general formula (1): . The method involves reaction of a hydrogen sulphide-saturated aldehyde of formula RCHO, where R=CH3, C2H5, n-C3H7, n-C4H9, n-C5H11, with 1,2-diaminoethane with molar ratio of initial reagents 1,2-diaminoethane: aldehyde: hydrogen sulphide equal to 10:60:40 at temperature 40°C and atmospheric pressure for 2.5-3.5 hours.

EFFECT: method of obtaining novel compounds which can be used as selective sorbents and extraction agents of precious metals, agents for protecting leather, fur and textile from biodeterioration, biologically active substances with respect to different microorganisms and sulphate-reducing bacteria.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 2(3H)-benzothiazolone. The method is realised by boiling bis-(2,2'-dimethoxycarboxamido)-phenyl disulphide with zinc dust for 7,5 hours in glacial acetic acid, followed by separating zinc salts, diluting the filtrate with ice water, filtering the crystalline product and washing said product with diluted HCl (1:1) and water and then drying on air and recrystallising from ethanol. The invention also relates to a method of producing 3-2-[2-oxo-1,3-benzothiazol-3(2H)-yl]ethyl-1,3-benzothiazol-2(3H)-one. The method is realised by boiling 2(3H)-benzothiazolone with 1,2-dibromoethane in acetone in the presence of K2CO3. Water is then added and the mixture is treated with diethyl ether, followed by washing the organic phase with 10% aqueous NaOH solution and water, drying with anhydrous potassium carbonate, removing the solvent and recrystallising from methanol. The invention relates to a method of producing 3-(2-chloroacetyl)-1,3-benzothiazol-2(3H)-one. The method is realised by boiling 2(3H)-benzothiazolone in anhydrous benzene with chloroacetyl chloride for 10 hours, then washing the cooled reaction mass with 2% aqueous NaOH solution, extracting with benzene, washing the merged extracts with water, drying with anhydrous calcium chloride and removing the solvent, followed by recrystallisation from chloroform.

EFFECT: improved method of producing 2(3H)-benzothiazolone derivatives.

3 cl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and specifically to a method of producing N-(1,5,3-dithiazepan-3-yl)amides of general formula (1):

where R=p-C5H4N (a), (CH3)3CO (b), o-CH3OC6H4 (c), which involves reaction of 1,2-ethanedithiol, which is first mixed with aqueous formaldehyde solution at 20°C, with a hydrazide of general formula RC(O)NHNH2 [R is as described above] in the presence of a copper chloride crystalline hydrate catalyst CuCl2·2H2O with molar ratio 1,2-ethanedithiol: CH2O: RC(O)NHNH2: CuCl2·2H2O = 10:20:10:(0.3-0.7), at 75-85°C and atmospheric pressure for 44-52 hours.

EFFECT: method of obtaining novel N-(1,5,3-dithiazepan-3-yl)amides, which can be used as biologically active compounds, selective sorbents and extractants of noble and precious metals.

1 cl, 1 tbl, 1 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to organic chemistry, particularly to a method for preparing 3-(m-, n-methylphenyl)-1,5,3 -dithiazepanes of general formula (1):

which consists in the fact that a mixture of formaldehyde and 1,2-ethandithiole prepared at 20°C for 30 min is added with the catalyst Sm(NO3)3·6H2O, m-, or n-methylaniline at molar ratio of m-, or n-methylaniline : formaldehyde : 1,2-ethandithiole : Sm(NO3)3·6H2O = 10 : 20 : 10 : 0.5, to be mixed at room (~20°C) temperature for 20-40 min in chloroform.

EFFECT: what is developed is a method for preparing new 3-(m-,n-methylphenyl)-1,5,3-dithiazepanes which can find application as antibacterial, antimycotic and antiviral agents as biologically active complexing agents, selective sorbents and extractants of precious metals, special agents for bacterial activity suppression in various technical media.

1 cl, 1 tbl, 1 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to organic chemistry, particularly to a method for preparing 3-{o-, m-, n-nitrophenyl)-1,5,3 -dithiazepanes of general formula (1):

which consists in the fact that a mixture of formaldehyde and 1,2-enandithiole prepared at 20°C for 30 min is added with the catalyst Sm(NO3)3·6H2O, o-(or m-, or n-)nitroaniline at molar ratio of o-(or m-, or n-)nitroaniline : formaldehyde : 1,2-enandithiole : Sm(NO3)3·6H2O = 10 : 20 : 10 : 0.5, to be mixed at room (~20°C) temperature for 20-40 min in chloroform.

EFFECT: what is developed is a method for preparing new 3-(o-, m-, n-nitrophenyl)-1,5,3-dithiazepanes which can find application as antibacterial, antimycotic and antiviral agents as biologically active complexing agents, selective sorbents and extractants of precious metals, special agents for bacterial activity suppression in various technical media.

1 cl, 1 tbl, 1 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to organic chemistry, particularly a method for preparing (1,5,3-ditiazepinan-3-yl)(thio)phenols of general formula (1) which consists in the fact that amino(thio)phenols (o-aminophenol, n-aminophenol, n-aminothiophenol) react with 1,3,6-oxaditiapinane in the presence of the catalyst Sm(NO3)3·6H2O in the molar ration of amino(thio)phenol : 1,3,6-oxaditiapinane : Sm(NO3)3·6H2O = 10 : 10 : (0.3-0.7) in the solvents of chloroform-ethanol (in volume ratio 1:1) in the argon environment for 2.5-3.5 h.

EFFECT: what is developed is a method for preparing new (1,5,3-ditiazepinan-3-yl)(thio)phenols which can find application as antibacterial, antimycotic and antiviral agents as biologically active complexing agents, selective sorbents and extractants of precious metals, special agents for bacterial activity suppression in various technical media.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining α,ω-bis-(1,5,3-dithiazepinan-3-yl)-alkanes, which can be applied as antibacterial, antifungal and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media (from light industry to oil). Essence of method lies in interaction of α,ω-alkanediamine with 1,3,6-oxadithiapinane in presence of catalyst SmCl3·6H2O with mole ratio α,ω-alkanediamine : 1,3,6-oxadithiapinane : SmCl3·6H2O=10:20:(0.3-0.7) at temperature ~20°C and atmospheric pressure for 2.5-3.5 h. Output of α,ω-bis-(1,5,3-dithiazepinan-3-yl)-alkanes (1) constitutes 72-85%.

EFFECT: increase of compound application efficiency.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining 3-(o-,m-,p-methoxyphenyl)-1,5,3-dithiazepanes, which can be applied as antibacterial, antifungal and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media. Essence of method lies in preliminary mixing of formaldehyde with 1,2-ethanedithiole with further addition of o-,m-,p- methoxyaniline and mixing at temperature ~20°C and atmospheric pressure for 20-40 minutes. Output of 3-(o-, m-, n-methoxyphenyl)-1,5,3-dithiazepanes (1) constitutes 59-87%.

EFFECT: increase of compound application efficiency.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: method of obtaining 3-aryl-1,5,3-dithiazepanes of general formula , where R=H, m-Me, n-MeO, m-NO2, lies in the following: 3-tret-butyl-1,5,3-dithiazepane is subjected to interaction with N-arylamines (aniline, m-methylaniline, n-methoxyaniline, m-nitroaniline) in presence of catalyst Sm(NO3)3·6H2O in mole ratio 3-tret-butyl-1,5,3-dithiazepane : N-arylamine : Sm(NO3)3·6H2O=10:(10-12):(0.3-0.7) in chlorophorm and argon atmosphere for 2.5-3.5 h.

EFFECT: elaborated is method of obtaining with high selectivity of novel 3-aryl-1,5,3-dithiazepanes, which can be applied as antibacterial, antifungal and antiviral agents, as complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: method of obtaining N-aryl-1,5,3-dithiazepanes of general formula (I): , where Ar = Ph, m-Me-C6H4, o-MeO~C6H4, n-NO2-C6H4, lies in the following: 1,3,6-oxadithiepane is subjected to interaction with N-arylamines (aniline, m-methylaniline, o-methoxyaniline, n-nitroaniline) in presence of catalyst Sm(NO3)3·6H2O in mole ratio 1,3,6-oxadithiepane : N-arylamine : Sm(NO)3)3·6H2O = 10:(10-12):(0.3-0.7) in chlorophorm and argon atmosphere for 2.5-3.5 h.

EFFECT: elaborated is method of obtaining with high selectivity of novel N-aryl-1,5,3-dithiazepanes, which can be applied as antibacterial, antifungal and antiviral agents, as complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining 2- and 4-(1,5,3-dithiazepinsan-3-yl) phenols, which can be applied as antibacterial, antifungal and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special agents for suppression of vital activity of bacteria in various technical media. Essence of method lies in preliminary mixing of formaldehyde with 1,2-ethanedithiole with further addition of o-, n-aminophenol and mixing at temperature ~20°C and atmospheric pressure for 2-4 hours. Output of 2- and 4-(1,5,3-dithiazepinsan-3-yl) phenols (1) constitutes 60-75%.

EFFECT: method improvement.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing N-phenyl(benzyl)-1,5,3-dithiazepinane-3-amines and 2,4-dimethyl-N-phenyl(benzyl)-1,5,3-dithiazepinane-3-amines of general formula (1): R=Ph, Bz; R'=H, Me, which involves first mixing formaldehyde or acetaldehyde with 1,2-ethanedithiol and then adding phenylhydrazine (benzylhydrazine) in molar ratio of initial reactants aldehyde: 1,2-ethanedithiol: phenylhydrazine (benzylhydrazine)=20:10:10 and stirring at temperature 0°C and atmospheric pressure for 2-4 hours.

EFFECT: method of obtaining novel compounds which can be used as antibacterial, antifungual and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special reagents for inhibiting bacterial activity in different process media.

1 cl, 1 tbl, 1 ex

FIELD: organic chemistry, organic synthesis, chemical technology.

SUBSTANCE: invention relates to a method for combined synthesis of 3,4-diphenyl-1,3,4-thiadiazolidine of the formula (1a): and 5,6-diphenyltetrahydro-1,3,5,6-dithiadiazepine of the formula (1b): Method involves interaction of formaldehyde aqueous solution saturated with hydrogen sulfide with 1,2-diphenylhydrazine in a buffer solution butanol-sodium butylate: n.-BuOH/n.-BuONa taken in the mole ratio 1,2-diphenylhydrazine : formaldehyde : hydrogen sulfide : sodium butylate = 1:2:1:2, respectively, at temperature 20-40°C and at stirring 3 h. The yield of the end substance of the formula (1a) is 39% and that of the formula (1b) is 22%. Synthesized substances can be used as selective sorbents and extractants of previous metals, special reagents for inhibition of vital activity of microorganisms in different media, biologically active substances used in synthesis of different medicinal preparations, for example, anti-bacterial, anti-fungal and anti-viral agents.

EFFECT: improved method of synthesis.

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