SU1456010A3 - Method of producing nitrogen-containing heterocyclic compounds - Google Patents

Abstract

The invention relates to heterocyclic compounds, in particular to the preparation of nitrogen-containing heterocyclic compounds of the formula IR -W- (-0-CH (Rg) -CH (R5) -XR where W and X are oxygen, sulfur; R is kil, C -Cj -alkenyl; R is hydrogen or lower alkyl; Rj is hydrogen, chlorine or lower alkyl; R is 2-pyridyl which may be substituted by a halogen atom in the 6-position, 2-pyrimidine 1, thiazol-2-yl, or 2-thiazoline- 2-yl, having insecticidal activity. Purpose: development of a method for producing new compounds. Synthesis is carried out from a compound of the formula R, -W-0-CH (RJ-CH (Rc) -Q), where R ,, R, RjHW above and Q is OH, halogen or CHj-SO-O-, and compounds of the formula R4. Q, where R is indicated above, and Qj is halogen, when Q is OH, or SH, when Q, is halogen or, and the obtained target product, or the obtained compound I, where Rj is H; X is S and W is O, and is chlorinated. 1 table § (U)

Description

t The invention relates to the field

obtaining new heterocyclic compounds, in particular derivatives

nitrogen-containing heterocycles of the general formula

four

01

O5

Ri-W-y-0-CH (R2) -CH (R3) -XR4

where W and X R.

Rj R - R. oxygen or seri; C J-C. Alkyl or CfCg alkenyl;

hydrogen or lower alkyl;

hydrogen, chlorine or lower alkyl;

2-pyridyl, which may be substituted by a halo atom

a gene at position 6, 2-pyrimidinyl, thia9ol-2-yl or 2-thiazolin-2-yl,

10 with insecticidal activity. The aim of the invention is to create, on the basis of known methods, a method of obtaining new compounds possessing a vigorous insecticidal activity.

cm

3, 14560104

The invention is illustrated by the example of purification of the residue by preparative thin-coatings. Layer chromatography 2-f2-4- (1 Example 1.K a mixture of methylpropoxy hydride) 11) enoxy-ethoxy} -minatrime (0.08 g), 5 ml of tetrahydrofuran (see table, compound 12).

on (THF) and 2 ml of hexamethylphosphoramide (HFA) cooled on ice

in the bath, 2-methyl-2C4- (1-methylpropoxy) phenoxy} ethanol is added dropwise.

Mass spectrum, t / e: 289 (Н). j;:; - Yield 78%.

Example 4. To sodium hydride (0.35, g, 14.6 mmol) in 20 ml

(0.63 g). The mixture was stirred with DMF at room temperature. 2-mercaptopopyrimidine (1.64 g, 14.6 mmol) was slowly added at 30, maintaining the reaction temperature at or below. After the anion had formed, slowly with cooling, maintaining the reaction temperature at 15-20 ° C, (1-methylpropoxy) -phenoxyethyl-bromide (4.0 g, 14.6 mmol) was added. The mixture was then heated to a foam temperature for 2 hours, a solution of 2-chloropyridine (0.38 g) in 5 ml THF was added and the mixture was stirred at 60 ° C for 3 hours. Then the THF was removed by evaporation rotary evaporator and the residue is purified by column chromatography on silica gel to give the product methyl 2-C4- (1-methylpropoxy) phenoxy-Zethoxy-pyridine (Art. Table, Compound 20 is stirred at room temperature 1).

Mass spectrum, w / e: 302 (). Yield 95%

Example 2: To a mixture of sodium hydride (0.12 g), 5 ml of THF and 4 ml of GMPA cooled in an ice bath are added dropwise a solution of (1-methyl-propoxy) phenoxy-ethanol (1.00 g) in 5 ml of THF. The mixture is stirred at room temperature for 2 hours, then 2,6-difluoropyridine (0.65 g) is added and stirred at room temperature. overnight, the THF was removed by rotary evaporation and the product was isolated by silica gel column chromatography to obtain 6-fluoro-2- {, 2- 4- (1-methylpropoxy) phenoxy J-ethoxyJ pyridine (see table, compound 7),

Mass spectrum, t / e:, 306 (M). Yield 95%

Example 3: Sodium hydride

re for 18 h, after which it is poured into water and extracted with ether. The combined organic extracts are washed with water and brine, dried and

25 is filtered and the solvent is removed to give, after purification, by preparative TLC (1-methylpropoxy) phenoxy-ethylthio-pyrimidine (see Table 2, compound 20).

30 Mass spectrum, t / e: 305 (M-t-H). Yield 94%.

Example 5. A mixture of 2- (4-isopropoxyphenoxy) ethanol (3.50 g), mesyl chloride (2.20 g) and triethylamine

35 (2.0 g) in 20 ml of methylene chloride is stirred at room temperature for 3 4j then poured into water and extracted with methylene chloride. The solvent is removed from the combined

40 organic extracts are evaporated on a rotary evaporator and the residue is purified by column chromatography to give 2- (4-isopropoxy-phenoxy) -ethylmethanes-capto-2-thiazoline (0.77 g) is treated with sodium hydride (0.32 g) and the resulting

(0.17 g, 7.14 mmol) in 10 ml of dimethylformamide (DMF) at room temperature.

A 1-methylpropane (1-methylpropoxy) was added following the procedure of Example 4, 2-merc) -phenoxy3-ethanol (1, 50 g, 7.14 mmol; 30 ml DIF. The mixture is heated to and stirred for 1 h. 2 -Chlorpyridine (0.94 g, 8.21 mmol) was added; the sodium salt was added to react with this mixture at 55 ° C, stirring with methanesulfonate with (1.50 g), roll for 1 hour. and then cooled. Receive (4-isopropoxyphenok- to room temperature. Reactions) -ethylthio -2-thiazoline (the mixture is poured onto ice and extracted with ether. The combined organic extracts are washed with water until neutral and brine, dried and filtered and the solvent is removed to obtain, after

55

61 tables). Yield 74%.

Example 6. N-Chlorosuccinimide (1.05 g, 7.9 mmol) was added portionwise to 2-14 (1-methylpropoxy) -phenoxy-1-thio-pyrimidine (2.0 g, 6.6 mmol) in carbon tetrachloride (see table, compound 12).

Mass spectrum, t / e: 289 (Н). j;:; - Yield 78%.

Example 4. To sodium hydride (0.35, g, 14.6 mmol) in 20 ml

DMF was slowly added at room temperature with 2-mercaptopopyrimidine (1.64 g, 14.6 mmol) at 30, keeping the reaction temperature at or below. After the anion was formed, (1-methylpropoxy) -phenoxyethyl-bromide (4.0 g, 14.6 mmol) was slowly, while cooling, maintaining the reaction temperature at 15-20 ° C. The mixture was then reused for 18 hours, after which it was poured into water and extracted with ether. The combined organic extracts are washed with water and brine, dried and

filtered and the solvent is removed to obtain after purification using preparative TLC (1-methylpropoxy) phenoxy ethylthio-pyrimidine (see table, compound 20).

Mass spectrum, t / e: 305 (M-t-H). Yield 94%.

Example 5. A mixture of 2- (4-isopropoxyphenoxy) ethanol (3.50 g), mesyl chloride (2.20 g) and triethylamine

(2.0 g) in 20 ml of methylene chloride is stirred at room temperature for 3 4j then poured into water and extracted with methylene chloride. The solvent is removed from the combined

organic extracts by evaporation on a rotary evaporator and the residue purified by column chromatography to give 2- (4-isopropoxyphenoxy) ethylmethanesulfonate.

Capto-2-thiazoline (0.77 g) is treated with sodium hydride (0.32 g) and the resulting

 Following the procedure of Example 4, 2-mer

sodium salt is introduced into the reaction with methanesulfonate with (1.50 g). A (4-isopropoxyphenoxy) ethylthio -2-thiazoline is obtained (compound

sodium salt is introduced into the reaction with methanesulfonate with (1.50 g). A (4-isopropoxyphenoxy) ethylthio -2-thiazoline is obtained (compound

61 tables). Yield 74%.

Example 6. N-Chlorosuccinimide (1.05 g, 7.9 mmol) was added portionwise to 2-14 (1-methylpropoxy) -phenoxy-1-thio-pyrimidine (2.0 g, 6.6 mmol) in tetrachloride coal 14

The mixture is heated to room temperature and stirred for 18 hours, then heated at 60 ° C for 32 hours. The reaction mixture is filtered and the solvent is removed to give 2-1-chloro after purification by chromatography. 2- 4- (1-methylpropoxy) -phenoxy-J-ethyl-thio pyrimidine (compound 44 tables) ..

Mass spectrum, t / e: 338 (M). Yield 10%.,.

The table lists the compounds of general formula (I) obtained according to the above procedures of Examples 1-6 using the appropriate starting materials.

Biological testing.

Example 7. A series of compounds of formula (I) are tested for contact activity relative to house flies using the following method.

The 30 larvae in the third instar migrating after feeding Musca domestica L. are individually topically treated with 1 µl of the test compound in acetone at different doses. As a control, the larvae were treated identically with 1 µl of acetone. The larvae were kept in closed containers for 7 days at 31 ° C and with an illumination period of 16 hours. The result was analyzed as Sflj, i.e. the dose required to cause an effect in 50% of the tested insects. Observed effects include direct toxicity (the larva has died), delayed toxicity (the cocoon died), and juvenile hormonal activity (the absence of fully adult hatching, chitin inhibition, cuticle deformation (skin), and pupation abnormality). Each of the compounds tested has an EDU of less than 0.0050 µg / grub.

The results of the experiments.

ED compounds, mg / ca.

3O.OOOU

70,0074

15

20

27

28 30

31

49 standard

0,0000032

0,0000017

0,00000013

0,000001 55

0,00064

0.031

0,000014

Q

g

5 Q

0

0

five

five

106

Compound (fenoxncarb) 0.11

Example 8. Compounds 2-f2- 4- (1-methylpropoxy) -phenoxyJ-ethoxypyridine (compound 3) and 2- (1-methyl-2-G4- (1-methylpropoxy) -phenoxy-ethoxy-pyridine (compound 2) is tested for activity against yellow fever-causing mosquitoes as follows.

The 20 larvae in the fourth instar stage (Aedes aegypty), 5 days after hatching, are placed in plastic containers with 50 ml of tap water mixed with 50 µl of the acetone solution of the test compound at the test concentration. A few drops of liver powder suspension are added as a source of nutrition. The containers are closed and kept at 28 ° C for a 16-hour period of illumination until all the larvae or pupae perish or are in the form of adult individuals. The assay is performed by expressing the effect as ED jj, which corresponds to the concentration required to cause the effect in 50% of the tested insects. Observed effects include direct toxicity (the larvae died), juvenile hormonal activity (cocoon death, and the absence of fully adult hatching). Each of the tested compounds has 0.0050 ppm.

NMR (CDCl) - characteristics of the compounds of the table (ppm).

Compound I: f 0.8-1.8 (multiplet, 11H); 3.9-4.8 (multiplet, 4H); 6.6-7.0 (multiplet, 6H); 7.3 - 7.7 (multiplet, 1H); 8.1-8.3 (multiplet, 1H).

Connection 2. SO 0.8-1.8 (multiplet, 11H); 3.9-4.3 (multiplet, 3N); 5.4-5.8 (multiplet, 1H); 6.7-7.0 (multiplet, 6H); 7.3-7.7 (multiplet, 1H); 8.1-8.3 (2 doublets, 1H).

Compound 3: (0.8-1.9 (multiplet, 8H); 4.1-4.4 (multiplet, ZN) 4.6-4.8 (multiplet, 2H); 6.7-7.0 ( multiplet, 2H); 6.7-7.0 (multiplet, 6H); 7.3-7.7 (multiplet, 1H); 8.1-8.3 (multiplet, 1H).

Compound 4: cC (2 singlet, 6H); 4.1-4.7 (multiplet, 6H); 5.4 (triplet, 1H); 6.8-6.9 (multiplet.

6H); 7.3-7.7 (multiplet, 1H); 8.0 - 8.2 (multiplet, 1H);

Connection 5: rf 1,6 (doublet, ZN); 1.9 (2 singlets, 6H); 4.2-4.7 (multiplet, AH); 5.5 (triplet, 1H); 6.8-6.9 (multiplet, 6H) j 7.3-7.7 (multiplet, 1H); 8.0-8.2 (multiplet, 1H),

Connection 7: if - 0.8-1.9 (multiplet, 8H); 3.9-4.4 (multiplet, 3N); 4.5-4.7 (multiplet, 2H); 6.3 - 6.7 (multiplet, 2H); 6.8 (4H singlet); 7.3-7.8 (quadruplet, 1H).

Connection 12: "G 0.95 (multiplet, ZN); 1.23 (doublet, 3N, J 6ru), centered at 4.18 and 4.23 (multiplet, 5H); 8.53 (doublet, 2H, J 5 Hz).

Connection 13: sG 0.96 (multiplet, ZN); 1.25 (doublet ZN, J 6 Hz); 1.50 (doublet, NN, J 6 Hz); 5.57 (sextet, 1H, J 6 Hz); 8.54 (doublet, 2H, J 5 Hz).

Connection 15: / 0,8-1,1 (triplet, ZN); 1.2 (doublet, SN); 1.2-1.7 (multiplet, 2H); 1.7-2.2 (hepatite, 1H); 4.2-4.9 (multiplet, 4H); 6.9 (doublet, 2H); 6.8-7.1 (multiplet, 1H); 7.4 (doublet, 2H); 8.5 (doublet, 2H).

Connection 16: "0.8-1.1 (triplet, MN); 1.2 (doublet, SN); 1.3-1.9 (multiplet, 2H); 2.7-3.3 (hepatite, 1H); 3.9-4.6 (multiplet, 2H); 5.4-5.7 (heptet, 1H); 6.8 (doublet, 2H); 6.7-7.1 (multiplet, 1H); 7.3 (doublet, 2H); 8.5 (doublet, 2H).

Connection 17: (f 1.6-1.8 (2 oak10

15

(multiplet, 2H); 2.7-3.3 (heptet 6H); 3.4-3.7 (triplet, 2H); 4.2-4 (triplet, 2H) ;. 6.8-7.0 (multiply 1H); 7.4 (doublet, 2H); 8.5 (duplicate 2H).

Compound 23: rf 0.94 (cartoon, 3N); 1.24 (doublet, 3N, a 6 3.50 (triplet, 2H, J 7 Hz); (triplet, 2H, J 7 Hz); 6.85 (singlet, 4H); 8.49 (doublet, 2H J 5 Hz).

Connection 0.90 (cartoon plet, ZN); 1.25 (doublet, NN, J 6 Hz); 3.51 (multiplet, 2H); crated at 4.19 (multiplet, 6.84 (multiplet, 4H); 8.51 (double 2H, J 5 Hz).

Compound 25; 0.92 (cartoon plet, 6H); 1.23 (doublet H, 3.50 (triplet, 2H, J 7 Hz); 4.2 (multiplet, 2H); 6.84 (singlet, 8.49 (doublet, 2H, J 5 Hz).

Compound 27: CG 0.95 (triple 25 EH, J 7.25 Hz); 1.24 (doublet, W J 5.9 Hz); 1.62 (multiplet, 2H 4.12 (multiplet, 3N); 4.72 (multiplet, 2H); 6.65 (doublet, 1H, J 22 Hz), 7.09 (doublet, 1H, J 30 3; 7 Hz).

Compound 28: (f 0.95 (trip ZN); 1.23 (doublet, ZN, J 5.9 D 1.60 (multiplet, 5H); 4.11 (mule plet, ZN); 5.44 (multiplet , 1H) 6.62 (doublet, 1H, J 3.7 Hz); 6 (singlet, 4H); 7.09 (doublet, 1H, J 3.9 Hz).

Compound 30: "0.98 (multi

20

h isdipepis i i, - i, u-i, u h, “u u h, h / tm t

years singlet, 6H); 4.2-4.8 (multiplet, 40 JH); 1.21 (doublet, SN, J

6H); 5.3-5.6 (triplet, 1H); 6.9 (singlet, 4H); 6.8-7.0 (multiplet, 1H); 8.5 (doublet, 2H).

Compound 18: tf 1.2 (doublet, 6H); 4.2-4.8 (multiplet, 5H); 6.8 (singlet, 4H); 6.8-7.0 (multiplet, 1H); 8.4 (doublet, 2H).

Connection 19: SO 0.9 (triplet, 6H); 1.2-1.9 (multiplet, 4H); 4.0 (p, 1H); 4.2-4.4 (multiplet, 2H); 4.6-6.9 (multiplet, 2H); 6.9 (singlet, 4H); 6.8-7.0 (multiplet, 1H); 8.5 (doublet, 2H).

Connection 20: C5 0.95 (multiplet, ZN); 1.23 (doublet, NN, J 6 Hz); 3.52 (multiplet, 2H); 8.53 (doublet, 2H, J 5 Hz).

Connection 21: 0,8-1,1 (triplet, ZN); 1.2 (doublet, SN); 1.2-1.8

 7 Hz); centered at 4.29 4.75 (multiplet, 4H); 6.67 (double 1H, J- 4 Hz); 6.86 (multiplet, 7.11 (doublet, 1H, J 4 Hz); 37 (multiplet, 2H).

Connection 31: sG 1.72 (double 6H, J 5.5 Hz); 4.20 (multiply 2H); 4.41 (doublet, 2H, J 6.6 G 4.69 (multiplet, 2H); 6.62 (multi 50 plet, 1H); 6.82 (singlet, 4H); 7 (multiplet, 1H).

Compound 34: 0.96 (triple EF, J 7.5 Hz); 1.25 (doublet, З J 6.2 Hz); 1.66 (multiplet, 55 3.44 (multiplet, 4H); 4.21 (mule plet, 5H); 6.82 (singlet, 4H).

Compound 35: / 0.98 (multi plet, MN); 1.20 (doublet, NN, L 7 3.42 (multiplet, 4H); 4.21 (mule

eight

),

b10

15

(multiplet, 2H); 2.7-3.3 (heptet, 6H); 3.4-3.7 (triplet, 2H); 4.2-4.4 (triplet, 2H) ;. 6.8-7.0 (multiplet, 1H); 7.4 (doublet, 2H); 8.5 (doublet, 2H).

Connection 23: rf 0.94 (multiplet, ZN); 1.24 (doublet, 3N, a 6 Hz); 3.50 (triplet, 2H, J 7 Hz); (triplet, 2H, J 7 Hz); 6.85 (singlet, 4H); 8.49 (doublet, 2H, J 5 Hz).

Connection 0.90 (multiplet, ZN); 1.25 (doublet, NN, J 6 Hz); 3.51 (multiplet, 2H); centered at 4.19 (multiplet, 3N); 6.84 (multiplet, 4H); 8.51 (doublet, 2H, J 5 Hz).

Compound 25; 0.92 (multiplet, 6H); 1.23 (doublet H,); 3.50 (triplet, 2H, J 7 Hz); 4.21 (m, 2H); 6.84 (singlet, 4H); 8.49 (doublet, 2H, J 5 Hz).

Connection 27: sG 0.95 (triplet, 25 MN, J 7.25 Hz); 1.24 (doublet, 3N; J 5.9 Hz); 1.62 (multiplet, 2H); 4.12 (multiplet, 3N); 4.72 (m, 2H); 6.65 (doublet, 1H, J 22 Hz), 7.09 (doublet, 1 H, J 30 3; 7 Hz).

Connection 28: (f 0.95 (triplet, ZN); 1.23 (doublet, ZN, J 5.9 Hz); 1.60 (multiplet, 5H); 4.11 (multiplet, ZN); 5.44 (multiplet, 1H); 6.62 (doublet, 1H, J 3.7 Hz); 6.82 (singlet, 4H); 7.09 (doublet, 1H, J 3.9 Hz).

Connection 30: "0.98 (multi20

uch, h / tm t

0 JH); 1.21 (doublet, SN, J

 7 Hz); centered at 4.29 and 4.75 (multiplet, 4H); 6.67 (doublet, 1H, J- 4 Hz); 6.86 (m, 2H); 7.11 (doublet, 1H, J 4 Hz); 37 (multiplet, 2H).

Connection 31: sG 1.72 (doublet, 6H, J 5.5 Hz); 4.20 (m, 2H); 4.41 (doublet, 2H, J 6.6 Hz); 4.69 (multiplet, 2H); 6.62 (multi-0 plet, 1H); 6.82 (singlet, 4H); 7.08 (multiplet, 1H).

Compound 34: 0.96 (triplet, 3N, J 7.5 Hz); 1.25 (doublet, NN, J 6.2 Hz); 1.66 (multiplet, 2H); 55 3.44 (multiplet, 4H); 4.21 (multiplet, 5H); 6.82 (singlet, 4H).

Connection 35: / 0,98 (multiplet, ZN); 1.20 (doublet, 3N, L 7 Hz); 3.42 (multiplet, 4H); 4.21 (multiplet, AH); 6.85 (m, 2H); 7.36 (multiplet, 2H).

Connection 38: with 1.2 (doublet, 6H); 3.2-3.6 (multiplet, 4H); 4.1 - 4.6 (multiplet, 5H); 6.8 (singlet, an).

Connection AO: 0.8-1.1 (triplet, ZN); 1.1-1.3 (doublet, ZN); 1.34, 05-4.31 (multiplet, 3N); 4.73 v (multiplate, 3N)} 6.67 (doublet, 1H, J 4 Hz); 6.83 (singlet, 4H); 7.11 (doublet, 1H, J 4 Hz).

Connection 52: with 0.92 (multiplet, 6H); 1.21 (doublet, 3N, 1 6 Hz) centered at 4.25 (m, 2H); centered at 4.72 (multi

1.9 (multiplet, 2H), 3.4-3.7 (triplet, 2H); 6.68 (multiplet, 1H);

years, 2H); 4.0-4.3 (multiplet, 3N); 6.9 (singlet, 4H); 6.7-7.6 (multiplet, 3N); 8.4 (doublet, 1H).

Compound 44: f 0.97 (multi 6, 75 (singlet, 4H); 7.12 (multiplet 1H).

Compound 53id 1,2 (doublet, 6H); 4.1-4.8 (multiplet, 5H); 6,6

Plet, ZN); 1.25 (doublet, 3N, L 6 Hz); 15 (doublet, 1H); 6.8 (singlet, 4H); 7.1

25

thirty

35

4.22 (multiplet, 1H, J 6 Hz); 4.46 (doublet, 2H, J 6 Hz); 6.38 (triplet, 1H, J 6 Hz); 8.64 (doublet, 2H, J 5 Hz).

Compound 45: CG 0.94 (multi-jo plet, MN); 1.24 (doublet, 3N, L 6 Hz); 4.25 (m, 2H); 4.65 (multiplet, 2H); 6.85 (singlet, 4H); 7.54 (multiplet, 1H); 8.13 (multiplet, 1H).

The connection A6: 0,90 (multiplet, ZN); 1.24 (doublet, 3N, 1 7Hz); 4.25 (m, 2H); 4.65 (multiplet, 2H); 6.84 (singlet, 4H); 7.54 (multiplet, 1H); 8.13 (multiplet, 1H).

Connection 47: Wed 0.95 (triplet, 6H); 1.2-2.0 (m, 4H); 3.8- 4.2 (p, 1H); 4.2-4.4 (triplet, 2H); 4.5-4.8 (triplet, 2H); 6.7-7.0 (multiplet, 2H); 6.8 (singlet, 4H); 7.3-7.7 (multiplet, 1H); 8.0-8.3 (multiplet, 1H),

Connection 48: CG 1,2 (doublet, 6H); 4.1-4.8 (multiplet, 5H); 6.8 (singlet, 4H); 6.7-1, B (multiplet, 3N); 8.0-8.5 (multiplet, 1H).

Connection 49: f 0.98 (multiplet, ZN); 1, (doublet, 3N, L 7 Hz); 1.52 (doublet, NN, J 7 Hz); 2.95 (m, 1H); 4.14 (multiplet, .2H); 5.43 (multiplet, 1H); 6.64 (doublet, 1H, J 4 Hz); 6.84 (multiplet, 2H); 7.11 (doublet, 1H., J 4 Hz); 7.36 (multiplet, 2H).

Connection 50: f 0.94 (multiplet, ZN); 1.25 (doublet, 3N, L 6 Hz); centered at 4.26 (multiplet, 2H); centered at 4.74 (multiplet, 2H); 6.68 (multiplet, 1H); , 6.83 (singlet, 4H); 7.11 (multiplet, 1H).

Connection 51: from 0.90 (multiplet, ZN); 1.25 (doublet, Wl, L 6 Hz);

40

45

50

(doublet, 1H).

Connection 54: SG 0.95 (triplet, 6H); 1.2-1.9 (multiplet, 4H); 3.8 - 4.2 (multiplet, 1H); 4.1-4.4 (multiplet, 2H); 4.6-4.8 (multiplet, 2H) 6.6 (doublet, 1H); 6.8 (singlet, 4H); 7.1 (doublet, 1H).

Connection 55: with 0.96 (multiplet, ZN); 1.2A (doublet, NN, J 6 Hz) 3.57 (multiplet, 2H); 4.07-4.30 (multiplet, 3N); 6.80 (singlet, 4H) 7.19 (multiplet, 1H); 7.65 (multiplet, 1 N).

Connection 56: G 0.97 (multi-, ZN); 1.19 (doublet, 3N, L 7 Hz) 1.46 (doublet, 3N, J 7 Hz); 2.94 (multiplet, 1H); 3.32 (triplet, GZ J 8 Hz); 3.92-4.29 (multiplet, 4H); 6.88 (m, 2H); 7.35 (multiplet, 2H).

Connection 57: cf 0.94 (multiplet, ZN); 1.25 (doublet, 3N, L 6 Hz 3.30-3.51 (multiplet, 4H); 4.11-4, (multiplet, 4H); 6.82 (singlet, 4H)

Connection 58: CG 0.90 (multiplet, ZN); 1.24 (doublet, 3N, L 6 Hz centered at 3.39 (multiplet 4H); centered at 4.19 (cartoon, 5H); 6.81 (singlet, 4H).

Connection 59: (f 0.92 (multiple years, 6H); 1.23 (doublet, 3N, L 6 Hz) centered at 3.40 (multiplet 4H); 3.99-4.40 (multiplet, 5H); 6 (singlet, 4H).

Compound 60: (f 0.95 (double triplet, 6H); 1.2-1.9 (multiplet, 4H); 3.4 (quadruplet, 4H); 3.8-4.3 (multiplet, 5H); 6.9 (singlet, 4H)

Claims (1)

Invention Formula Method for preparing nitrogen-containing heterocyclic compounds of general formula I 10to 4.05-4.31 (multiplet, 3N); 4.73 v (multiplate, 3N)} 6.67 (doublet, 1H, J 4 Hz); 6.83 (singlet, 4H); 7.11 (doublet, 1H, J 4 Hz). Connection 52: with 0.92 (multiplet, 6H); 1.21 (doublet, 3N, 1 6 Hz), centered at 4.25 (m, 2H); centered at 4.72 (multiplet, 2H); 6.68 (multiplet, 1H); plet, 2H); 6.68 (multiplet, 1H); 6.75 (singlet, 4H); 7.12 (multiplet, 1H). Compound 53id 1,2 (doublet, 6H); 4.1-4.8 (multiplet, 5H); 6,6 (doublet, 1H); 6.8 (singlet, 4H); 7.1 (doublet, 1H); 6.8 (singlet, 4H); 7.1 five 0 five 0 five 0 (doublet, 1H). Connection 54: SG 0.95 (triplet, 6H); 1.2-1.9 (multiplet, 4H); 3.8 - 4.2 (multiplet, 1H); 4.1-4.4 (multiplet, 2H); 4.6-4.8 (multiplet, 2H); 6.6 (doublet, 1H); 6.8 (singlet, 4H); 7.1 (doublet, 1H). Connection 55: with 0.96 (multiplet, ZN); 1.2A (doublet, NN, J 6 Hz); 3.57 (multiplet, 2H); 4.07-4.30 (multiplet, 3N); 6.80 (singlet, 4H); 7.19 (multiplet, 1H); 7.65 (multiplet, 1 N). Connection 56: G 0.97 (multi-, ZN); 1.19 (doublet, 3N, L 7 Hz); 1.46- (doublet, 3N, J 7 Hz); 2.94 (multiplet, 1H); 3.32 (triplet, 3N, J 8 Hz); 3.92-4.29 (multiplet, 4H); 6.88 (m, 2H); 7.35 (multiplet, 2H). Connection 57: cf 0.94 (multiplet, ZN); 1.25 (doublet, 3N, L 6 Hz); 3.30-3.51 (multiplet, 4H); 4.11-4.30 (multiplet, 4H); 6.82 (singlet, 4H). Connection 58: CG 0.90 (multiplet, ZN); 1.24 (doublet, 3N, L 6 Hz); centered at 3.39 (multiplet, 4H); centered at 4.19 (multiplet, 5H); 6.81 (singlet, 4H). Connection 59: (f 0.92 (multiplet, 6H); 1.23 (doublet, 3N, L 6 Hz); centered at 3.40 (multiplet, 4H); 3.99-4.40 (multiplet, 5H); 6.82 (singlet, 4H). Compound 60: (f 0.95 (double triplet, 6H); 1.2-1.9 (multiplet, 4H); 3.4 (quadruplet, 4H); 3.8-4.3 (multiplet, 5H); 6.9 (singlet, 4H). Invention Formula Method for preparing nitrogen-containing heterocyclic compounds of general formula I Ri-W-y-0-CHlR2) -CH (R3) -XR4 where w and x R, R, Rj oxygen or sulfur; Cj-C-alkyl or C-C-alkenyl; hydrogen or lower alkyl; R4 is 2-pyridyl, which can be substituted by a gav atom in the 6, 2-pymidinyl, thiazol-2-yl or 2-thiazolin-2-sh1 position, hydrogen chlorine or lower 10 characterized by the fact that. alkyl compound of general formula II RI-W- V- 0-CH (R2) - CH (R3) qQi where K, K, have the indicated meanings; Q - halogen, -OH or a group of the formula, is subjected to mutual where R has the indicated value; Q2-halogen, when Q, is OH, or Q is SH group, when Q is halogen or CH.J-SO is a 0 interaction with a compound of the general form- 20 obtained target product “ul, or the obtained compound I, where Rj is hydrogen, X is sulfur and W is oxygenated by chlorine.  Q t 2-pyridyl, which may be substituted by a halogen atom in the 6, 2-pyrimidinyl, thiazol-2-yl or 2-thiazolin-2-sh1 position, where R has the indicated value; Q2 is halogen, when Q, is OH, or Q is SH group, when Q is halogen or CH.J-SO is 0,  the obtained target product or the obtained compound I, where  the obtained target product or the obtained compound I, where Rj is hydrogen, X is sulfur and W is oxygenated chlorine. 56 СНзСН, СН (СНз) (СН) 8- (2-Thiazolin-2-yl) 57CH (CH,) CH (CHE) 0CHjCH - 58CHj (CH,) 5CH (CH5) 0CH, jCHj- 59 (CH3). CH-CH CH (CH2) 0CHjCH-60 (C2Hj) jCH-0CH CH - - 61 (СНз) 2СН-0CHiCHi