Method for substituted quinolines production from aniline, 1,2-diols and ccl4 under iron catalysts

FIELD: chemistry.

SUBSTANCE: invention relates to a method for preparation of substituted quinolines of the formula shown below , where R1=CH3, R2 and R3=H; R1=CH2CH3, R2=CH3 and R3=H; R1=CH2CH3, R2=H and R3=CH3; R1=CH2CH2CH3, R2=CH2CH3 and R3=H; X=H, o-CH3, "м"-CH3, "п"-CH3, o-C2H5, o-Cl, "м"-Cl, "п"-Cl, "п"-OMe, o-OH, from aniline, wherein the substituted anilines of formula XC6H4NH2 where X is as defined above, is reacted with 1,2-diols (1,2-ethylene glycol, 1,2-propanediol or 1,2-butanediol) and CCl4 in the presence of a catalyst selected from FeCl3⋅6H2O, FeCl3, FeCl24H2O, Fe(C5H5)2, Fe(acac)3, Fe(OAc)2 and Fe2(CO)9, at a molar ratio [catalyst]:[aniline]:[CCl4]:[1,2-diol] = 1:100: 200:400, at 150 °C for 8 hours.

EFFECT: process for preparation of quinoline derivatives that are raw materials for corrosion inhibitors, dyes and medicines production from available initial reactants.

1 tbl, 35 ex

 



 

Same patents:

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of formula I and formula IV wherein the radical values are such as specified in cl. 1 and 4 of the patent claim, as well as to their therapeutically acceptable salts. Besides, the invention refers to a composition for treating cancer on the basis of the compounds of formula I, to using the compounds of formula I for preparing the therapeutic agent for treating cancer, as well as to using it for treating cancer.

EFFECT: there are prepared and described the new compounds which inhibit anti-apoptotic Bcl-2 and Bcl-x protein activity.

17 cl, 481 ex

FIELD: chemistry.

SUBSTANCE: invention relates to 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives of formula I

or pharmaceutically acceptable salts thereof, where R1 denotes (1-6C)alkyl; R2, R3 independently denote halogen, (1-4C)alkoxy; R4 denotes phenyl or a 5-6-member heteroaryl, having one or two heteroatoms selected from nitrogen, oxygen or sulphur, phenyl or said heteroaryl, substituted with R7 and optionally substituted on the (hetero)aromatic ring with one or two substitutes selected from halogen, nitro, trifluoromethyl and (1-4C)alkyl; R7 denotes H, (1-4C)alkylthio, (1-4C)alkylsulphonyl, R8R9-amino, R10R11-aminocarbonyl, R12R13-amino(1-4C)alkylcarbonyl-amino, R14R15-amino(1-4C)alkyl, R16-oxy, R17R18-aminocarbonyl (1-4C)alkoxy, R19-oxy(1-4C)alkyl, R19-oxycarbonyl(1-4C)alkyl, R20R21-aminosulphonyl, R20-oxysulphonyl, aminoiminomethyl, (di)(1-4C)alkylaminoiminomethyl, morpholinyliminomethyl, trifluoromethylsulphonyl; R23-oxycarbonyl, or R23R24-aminocarbonyl; R8 denotes H or (1-4C)alkyl; R9 denotes (1-4C)alkylsulphonyl, (1-6C)alkylcarbonyl, (2-6C)alkenylcarbonyl, (3-6C)cycloalkylcarbonyl, (1-4C)alkoxycarbonyl, (3-4C)alkenyloxycarbonyl, (di)(1-4C)alkylaminocarbonyl, piperazinylcarbonyl, (5-8C)alkyl, (3-6C)cycloalkyl(1-4C)alkyl or phenylcarbonyl, furylcarbonyl, thiophenylsulphonyl, 5-member heteraryl(1-4C)alkyl, having one or two nitrogen atoms, optionally substituted on the heteroaromatic ring with one, two or three substitutes selected from hydroxy, amino, halogen, nitro, trifluoromethyl, (1-4C)alkoxy; R10 denotes H or (1-4C)alkyl; R11 denotes hydroxy(2-4C)alkyl, (1-4C)alkoxy(2-4C)alkyl; R12, R13 independently denote H, (1-6C)alkyl, (3-6C)-cycloalkyl, (1-4C)alkoxy(2-4C)alkyl, (3-6C)cycloalkyl-(1-4C)alkyl, pyrrolidinyl(1-4C)alkyl, amino(2-4C)alkyl, (di)(1-4C)-alkylamino(2-4C)alkyl or phenyl(1-4C)alkyl, pyridinyl (1-4C)alkyl; or R12R13 in R12R13-amino(1-4C)alkylcarbonylamino can be bonded together with the nitrogen atom to which they are bonded into a (5-6C)heterocycloalkyl ring, having one or two nitrogen atoms, optionally substituted with hydroxy(1-4C)alkyl; R14, R15 independently denote H, (1-6C)alkyl, (1-6C)alkylcarbonyl, (1-4C)alkoxycarbonyl or pyridinyl(1-4C)alkyl, optionally substituted on the aromatic ring with one substitute selected from halogen; or R16 denotes (di)(1-4C)alkylamino(2-4C)alkyl, hydroxycarbonyl(1-4C)alkyl, (1-4C)alkoxycarbonyl(1-4C)alkyl, phenyl(1-4C)alkyl or pyridinyl(1-4C)alkyl; R17, R18 independently denote H, (1-6C)alkyl, thiophenyl(1-4C)alkyl; or R17R18 in R17R18-aminocarbonyl(1-4C)alkoxy can be bonded into a morpholine or piperazine ring, R19 denotes H or (1-6C)alkyl; R20R21 independently denote H, (1-6C)alkyl or (1-4C)alkoxy(1-4C)alkyl; or R20R21 in R20R21-aminosulphonyl can be bonded into a morpholine ring; X denotes O or N-R22; Y denotes CH2 or C(O); Z denotes CN or NO2; R22 denotes H; R23, R24 independently denotes H; (1-4C)alkyl; or R23R24 in R23R24-aminocarbonyl can be bonded into a dihydropyridine ring; provided that compounds of formula I, in which X denotes O, R4 denotes phenyl and R7 is selected from H, (1-4C)alkylthio, (1-4C)alkylsulphonyl, R23-oxycarbonyl, and R23R24-aminocarbonyl, and compounds of formula I, in which X denotes O, R4 denotes (2-5C)heteroaryl and R7 denotes H are excluded. The invention also relates to use of 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives to prepare a medicinal agent for treating sterility.

EFFECT: improved useful biological properties.

12 cl, 73 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to 2-methyl-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydrochinoline derivatives of formula 1 , in which R1 represents (1-6C)alkyl; R2 represents halogen; R3 represents SO2NR5R6 or (1-4C)alkoxy; X represents O or NR7; R4 represents R8-(2-8C)alkyl, R8-(3-8C)alkenyl or R8-(2-4C)alkoxy-(2-4C)alkyl; Z represents CN or NO2; R5 and R6 independently on each other represent H or (1-4C)alkyl; or R5 together with R6 and N, to which they are bound, form 5-6-member saturated ring, optionally containing additional heteroatom, selected from O; R8 represents OH, (1-4C)alkoxy, NH2; NR9C(O)R11, NR9SO2R11 or C(O)NR9R10; R7 and R9 independently represent H or (1-4C)alkyl; R10 represents (1-4C)alkyl; R11 represents (1-4C)alkyl, (1-4C)alkoxy(1-4C)alkyl, (3-6C)cycloalkyl, (1-4C)alkoxy or phenyl, or (4-5C)heteroaryl, and (4-5C)heteroaryl stands for aromatic group, which has 4-5 carbon atoms and at least one heteroatom, selected from N and O; or to their pharmaceutically acceptable salts. Invention also relates to pharmaceutical composition, as well as to application of 2-methyl-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydrochinoline derivatives.

EFFECT: obtaining novel biologically active compounds, possessing agonistic activity with respect to FSH receptor.

8 cl, 33 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to novel derivatives of 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydrochinoline, represented by formula , where R1 represents (1-6C)alkyl; R2 represents halogen, (1-4C)alcoxy; R3 represents OH, NO2, CN, fluoridated with (1-4C)alkoxy, (1-4C)alkoxy(2-4C)alkoxy. hydroxy(2-4C)alkoxy, (1-4C)alkoxycarbonyl, R7, R8-amino, R9, R10-amino, R9, R10-aminocarbonyl, R9, R10-aminosulfonyl or phenyl(1-4C)alkoxy, where phenyl ring in composition phenyl(1-4C)alkoxy is optionally substituted with one or several substituents, selected from (1-4C)alkoxy; R4 represents R11-phenyl or R11-(4-5C)heteroaryl, which represents heteroaromatic group, containing 4-5 carbon atoms and at least one heteroatom, selected from N and S, where phenyl or heteroaryl group is optionally additionally substituted with one or several substituents, selected from nitro, (1-4C)alkyl, (1-4C)alkoxy; R7 represents H, (1-4C)alkyl; R8 represents (1-4C)alkylsulfonyl, (1-4C)alkylcarbonyl, (1-4C)alkoxycarbonyl, (1-4C)alkoxy(1-4C)alkylcarbonyl, furylcarbonyl; phenyl(1-4C)alkylcarbonyl, where phenyl ring is optionally substituted with one or several substituents, selected from (1-4C)alkoxy; R9 and R10 are not necessarily selected from H, (1-6C)alkyl and (1-4C)alkoxy(2-4C)alkyl; or R9 and R10 can be bound together with formation of morpholinyl ring; R11 represents H, R12, R13-amino, R14, R15-aminocarbonyl or R14, R15-aminosulfonyl; R12 represents H; R13 represents (1-4C)alkylsulfonyl, (1-4C)alkylcarbonyl, (1-4C)alkoxycarbonyl or pyperazinyl(1-4C)alkylcarbonyl; R14 and R15 are independently selected from H, (1-6C)alkyl, (1-4C)alkoxy(2-4C)alkyl and imidazolyl(1-4C)alkyl; X represents O or R16-N; Y represents CH2 or C(O);Z represents CN; R16 represents H, (1-4C)alkyl, (1-4C)alkylcarbonyl; or their pharmaceutically acceptable salts. Invention also relates to pharmaceutical composition, as well as to application of 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydrochinoline derivatives by any of i.i. 1-10.

EFFECT: obtaining novel biologically active compounds, which possess agonistic activity with respect to FSH receptor.

13 cl, 43 ex

FIELD: chemistry.

SUBSTANCE: invention describes compounds of formula (1) , where substitutes are as defined in paragraph 1 of the invention. The compounds have fungicide properties. The method of obtaining formula (1) compounds is described, in which n equals 0. Described also is a fungicide composition based on formula (1) compounds and a phytopathogenic fungus control method which uses compounds in paragraph 1 or a composition based on the said compounds.

EFFECT: obtaining novel compounds which can be used as fungicides.

24 cl, 312 tbl, 14 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel derivative of tetrahydroquinoline of formula (1a) , in which R denotes cyclopentyl or isopropyl, as well as salts, solvate and salt solvates thereof.

EFFECT: novel compounds which can be used as a cholesterol ester transfer protein (CETP) inhibitor are obtained and described.

1 cl, 6 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to compounds of formula (I) , where R1 is hydrogen, C1-C7 alkyl; R2 is C1-C7 alkyl, aryl, C1-C7 haloalkyl or C3-C8 cycloalkyl; R3, R4 each independently represents hydrogen, halogen, C1-C7 alkoxy, C1-C7 alkylsuphonyl; R5 is hydrogen, halogen, C1-C7 alkyl, C1-C7 haloalkoxy, or aryloxy, or is -NR7R8, where R7 and R8 represent C1-C7 alkyls, or R7 and R8 together with the nitrogen atom to which they are bonded can form a 4-7-member heterocycloalkyl group, which can be substituted with one or more substitutes selected from a group consisting of halogen, C1-C7 alkyl, C1-C7 alkoxy, hydroxyl, phenyl and di(C1-C7)alkylamino; R6 is hydrogen or together with R5 can form a 5- or 6-member heterocycloalkyl group which can be substituted with one or more halogens; and their pharmaceutically acceptable salts of acid compound, except the range of compounds given in paragraph 1 of the formula of invention. The invention also relates to medicine based on said compounds, with activity of allosteric enhancer of GABA-B receptors and use of compounds of the formula to prepare medicines used in treating central nervous system disorders, including anxiety and depression.

EFFECT: novel compounds are obtained and described, which can be used for preparing medicines used in treating central nervous system disorders, including anxiety and depression.

14 cl, 58 ex, 1 tbl

FIELD: chemistry, medicine.

SUBSTANCE: invention refers to the method for modulation of the CRTh2-receptor activity with usage of the compounds of formula (I) or their pharmaceutically acceptable salts where: W is O, S(O)n (where n is equal 0, 1 or 2), NR15, CR1OR2 or CR1R2; X is hydrogen, halogen or C1-6 alkyl which can be substituted with one or more halogen atom; Y is hydrogen, halogen; Z is phenyl, pyridyl, pyrimidyl or quinolyl possibly substituted with one or more substituting group independently selected from following groups: halogen, CN, nitro, SO2R9, SO2NR10R11, CONR10R11, NHSO2R9 or C1-3 alkyl substituted with one or more halogen atom; R1 and R2 are independently hydrogen atom or C1-6 alkyl; R9 is C1-6 alkyl; R10 and R11 are independently hydrogen atom or C1-6 alkyl; R15 is hydrogen atom or C1-6 alkyl.

EFFECT: improvement of the method.

19 cl, 68 ex

FIELD: chemistry.

SUBSTANCE: description is given of N-alkenyl-2-quinolineoxyalkylamides with general formula (1) in which one of the radicals X and Y represents N or N-oxide, and the other represents CR or both X and Y represent N; Z represents H, halogen, C1-C6alkyl; R represents H, halogen, a cyano group; R1 represents C1-C4alkyl, or R1 represents alkoxylkyl, in which the total number of atoms of carbon is 2 or 3, or R1 represents a straight chain C1-C4alkoxy group; R2 represents H; R3 and R4 independently represent C1-C3alkyl; and R5 represents H, C1-C4alkyl optionally substituted with a halogen, a hydroxyl group, a C4-C6alkoxy group, cyano group, -S(O)n-C1-C6alkyl, where n represents 0, tri-C1C4alkylsilyloxy group. Description is given of the method of obtaining compounds with formula (1). Description is also given of a fungicide composition based on a compound with formula (1) and the method of fighting pathogenic fungi, using a formula (1) compound or composition.

EFFECT: the compounds have fungicide action, which allows for using them in agriculture.

10 cl, 16 ex, 152 tbl

FIELD: blasting.

SUBSTANCE: description is given of 6-ethoxy-1,2,2,4-tetramethyl-1,2-dihydroquinoline of a general formula (I) , where a double linkage in position 3-4 is shown dotted, R - is a residual of CH3; being used as a component for increasing the resistance of hydrocarbon fuels to detonation. A description is also given of the application of 6-ethoxy-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline, 6-ethoxy-1,2,2,4-tetramethyl-1,2-dihydroquinoline and 6-ethoxy-1,2,2,4-tetramethyl-1,2,3,4- tetrahydroquinoline and their mixtures as components for increasing the resistance of hydrocarbon fuels to detonation and of a fuel composition comprising hydrocarbon fuels and an additive improving its resistance to detonation.

EFFECT: using a new composition that possesses useful properties.

FIELD: chemistry.

SUBSTANCE: described is an improved method of producing substituted quinolines of general formula , where X=H, o(m, p)-CH3, o-C2H5, p-OCH3, o(m, p)-Cl, 3,4-(Cl)2, R = H, CH3 or C2H5, by reacting substituted anilines of formula XC6H4NH2, where X assumes values given above, with an alcohol RCH2CH2OH, where R assumes values given above, and CCl4 in the presence of a catalyst FeCl3·6H2O with molar ratio [catalyst]:[aniline]:[CCl4]:[RCH2CH2OH]=1:100:100:200, at 140°C for 2 hours; the obtained reaction mass is neutralised; the organic layer is extracted with CH2Cl2, filtered and the solvent is distilled; FeCl3·6H2O, CCl4,RCH2CH2OH, taken in ratio of 1:100:200, are added to the separated residue and the second reaction step is carried out at 140°C for 2 hours. Output of substituted quinolines is 11-94%.

EFFECT: low cost of the end product owing to use of readily available reactants and catalyst.

1 tbl, 30 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 2- and 2,3-substituted quinolines, involving reaction of aniline with aliphatic alcohols in the presence of a FeCl3·6H2O catalyst in a medium of tetrachloromethane at 140°C for 2-8 hours, via 1-3 steps of feeding reactants in molar ratio [catalsyt]:[aniline]:[CCl4]:[ROH]=1:100:100:200.

EFFECT: low cost of the end product owing to use of readily available reactants.

1 cl, 17 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and specifically to a method for combined synthesis of 4-alkylquinoline and (2,3-dialkyl-4-quinolinyl)-N,N-dimethylmethane amine of formula (1) and (2), which involves reaction of o-iodoaniline with N,N-dimethyl-2-alkyne-1-amine (where the alkyne is heptyne, octyne, undecyne) in the presence of lithium chloride (LiCl), potassium carbonate (K2CO3) and a palladium catalyst Pd(OAc)2 in molar ratio of o-iodoaniline: N,N-dimethyl-2-alkyne-1-amine: LiCl: K2CO3: Pd(OAc)2=10:(25-35):10:(25-35):(0.5-1.0), at temperature 90-110°C and atmospheric pressure, preferably at 100°C for 18-22 hours in dimethyl formamide as a solvent.

EFFECT: novel method for combined synthesis of 4-alkylquinoline and 2,3-dialkyl-4-quinolinyl-N,N-dimethylmethane amine, which can be used in fine organic synthesis.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic synthesis, and particularly to a method for synthesis of 2-propyl-3-ethylquinoline The method involves reaction of aniline with butyl aldehyde in the presence of an iron chloride crystallohydrate catalyst FeCl3·6H2O at atmospheric pressure, temperature 20°C, for 10 minutes in a dimethyl formamide or EtOH solvent.

EFFECT: novel method for synthesis of 2-propyl-3-ethylquinoline, characterised by low economical and time expenses.

1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to zinc 2-propyl-3-ethyl-8-oxyquinoline- chloride complexonate of formula , which is inhibitor of steel corrosion in mineralised media with high oxygen content.

EFFECT: obtaining of zinc chloride, which possesses higher efficiency as inhibitor of steel corrosion in mineralised media with high oxygen content and can be applied in oil producing industry, in particularly in system of waste waters utilisation, as well as in systems of circulating water supply of industrial enterprises.

1 cl, 1 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of general formula (I) , in which A is selected from one or several X and/or Y groups; X represents methylene group; Y represents C2-alkinylene group; n represent integer number from 1 to 5; R1 represents group R2, optionally substituted with one or several R3 and/or R4 groups; R2 represents group selected from pyridinyl, pyrimidinyl, pyridazinyl, imidazolyl, oxazolyl, pyrazolyl, isoxazolyl, oxadiazolyl, naphtyl, chinolinyl, isochinolinyl, dihydroisochinolinyl, 2-oxo-3,4-dihydrochinolinyl, indolyl, benzimidazolyl, pyrrolopyridinyl; R3 represents group selected from halogen atoms, groups C1-6-alkyl, C3-7-Cycloalkyl, C1-6-alkoxy, NR5R6 and phenyl; R4 represents group selected from groups: phenyl, naphtyl, pyridinyl; R4 group or groups can be substituted with one or several R3 groups, similar or different from each other; R5 and R6 independently on each other represent C1-6-alkyl group; R7 represents hydrogen atom or C1-6-alkyl group; R8 represents hydrogen atom or group C1-6-alkyl, C3-7-cycloalkyl, C3-7-Cycloalkyl- C1-3-alkylene; in form of base, acid-additive salt, hydrate or solvate. Invention also relates to methods of obtaining formula (I) compound by any of ii. 1-3, to compounds, determined by general formula (IV), (VII), to pharmaceutical composition, as well as to application of formula (I) compounds by any of ii. 1-3.

EFFECT: obtaining novel biologically active compounds possessing activity of enzyme FAAH inhibitors.

10 cl, 5 ex, 1 tbl

FIELD: organic chemistry, organic synthesis, chemical technology.

SUBSTANCE: invention relates to a method for synthesis of 2,3-dialkylquinolines. Invention describes a method for synthesis of 2,3-dialkylquinolines of the general formula: wherein R means C2H5, C3H7, C4H9 by interaction of aniline of the formula: C6H5NH2 with aliphatic aldehydes of the general formula: R-CH2CHO (wherein R has above given values) in the presence of a catalyst and wherein terbium nitrate crystal hydrate of the formula: Tb(NO3)3 x 6 H2O in the mole ratio C6H5NH2 : R-CH2CHO : Tb = 45:100:1.2, and reaction is carried out in dimethylsulfoxide (DMSO) medium as a solvent under atmosphere pressure and temperature 20°C for 10 min. Invention provides simplifying technology in synthesis of the end product.

EFFECT: improved method of synthesis.

1 tbl, 1 ex

FIELD: organic chemistry.

SUBSTANCE: invention relates to method for production of derivatives of general formula , wherein R is C2H5, C3H7, C4H9. Claimed method includes reaction of aniline with aliphatic aldehydes in presence of catalyst. Method is characterized in that as catalyst crystallohydrate of lanthanide trichloride (LnCl3.6H2O, Ln = Pr, Nd, Eu) and triisobutylaluminum (iso-Bu3Al)in LnCl3.6H2O:(iso-Bu3Al) molar ratio of 1:12 are used. Process is carried out in air, under atmospheric pressure and room temperature in toluene for 25 min. quinoline and derivatives thereof are useful in synthesis of cyan dyes, as extractants, sorbents and corrosion inhibitors.

EFFECT: simplified method with increased yield.

1 cl, 1 tbl, 7 ex

FIELD: organic chemistry.

SUBSTANCE: invention relates to method for production of derivatives of general formula , wherein R is C2H5, C3H7, C4H9. Claimed method includes reaction of aniline with aliphatic aldehydes of general formula RCH2CHO, wherein R is as defined above in presence of catalyst. Method is characterized in that as catalyst crystallohydrate of lanthanide trichloride (LnCl3.6H2O, Ln = Pr, Nd, Eu) is used. Process is carried out in C6H5NH2:RCH2CHO:LnCl3.6H2O molar ratio of 45:100:1.2, in air, under atmospheric pressure and room temperature in ethanol for 25 min. Quinoline and derivatives thereof are useful in synthesis of cyan dyes, as extractants, sorbents and corrosion inhibitors.

EFFECT: simplified method with increased yield.

1 cl, 1 tbl, 7 ex

FIELD: organic synthesis catalysts.

SUBSTANCE: catalyst consists of complex [Sm(NO3)5][C5H5NH]2 constituted by lanthanum nitrate, pyridine, and nitric acid taken in molar ratio 1:2:2, respectively.

EFFECT: achieved accessibility of catalyst.

1 tbl, 2 ex

FIELD: organic synthesis catalysts.

SUBSTANCE: catalyst consists of complex [Nd(NO3)7][C5H5NH]4 constituted by neodymium nitrate, pyridine, and nitric acid taken in molar ratio 1:4:4, respectively.

EFFECT: achieved accessibility of catalyst.

1 tbl, 2 ex

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