(3z)-4-aryl-hydroxy-1-(1,3,3-trimethylindolin-2-ylidene)but-3-en-2-ones and synthesis method thereof

FIELD: chemistry.

SUBSTANCE: invention relates to novel (3Z)-4-aryl-4-hydroxy-1-(1,3,3-trimethylindolin-2-ylidene)but-3-en-2-ones of general formula 3: Ar=Ph (a), C6H4Me-n (b), C6H4Cl-n (c), C6H4OEt-n (d), which exhibit fluorescent properties and can be used as products for synthesis of novel heterocyclic systems, as well as substances for marking samples and additives for light-reflecting paints. Synthesis method thereof is described.

EFFECT: obtaining novel compounds.

4 cl, 4 ex

 

The invention relates to the field of organic chemistry, namely to new individual compounds of class 2-methylene-1,3 .3m-trimethylindolenine (Fischer indole) and method of production thereof, which exhibit fluorescent properties and can be used as products for the synthesis of new heterocyclic systems, as well as substances for sample labeling and additives for reflective paints.

There are various solutions to protect monetary documents, shares, cheques, credit cards, identity cards, passports, using special inks, particularly inks with varying effect, allowing, for example, to move from blue to green depending on the tilt of the document, or paints, which begin to glow only at a certain irradiation, such as ultraviolet radiation (see U.S. patent No. 4175776, IPC 42D 15/00, priority 27.11.78 year). However, the range of these colors at present, small.

Know the use of special paints containing reflecting the substance and, if necessary, aluminum powder (see U.S. patent No. 4066280, IPC 42D 15/00, priority 03.01.78 year). The disadvantage of applying this paint is the complexity of the drawing on the paper, which leads to restriction of areas of its use relative to the total area of the document.

Of l is teratory known closest analogues of the claimed compounds (2Z)-1-aryl-3-hydroxy-5-(1,3 .3m-trimethylindolenine-2-ilidene)Penta-2-ene-1,4-diones (3A, b), not possessing fluorescent properties. The method of obtaining data derived Fischer indole lies in the interaction of 5-allfurn-2,3-diones (1A, b) with 2-methylene-1,3 .3m-trimethylindolenine (2) (Han, Sungurov, Annalies. Zhur.org.chem., 2009, 45, 958-959):

The disadvantages of this method include the inability to obtain similar compounds with side chain of four carbon atoms.

The objective of the invention is to develop a method for the synthesis of undescribed in the literature (3Z)-4-aryl-4-hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)but-3-EN-2-ones (3A-g)exhibiting fluorescence properties, as well as the expansion of the means, are used as labels to protect documents from unauthorized copying and additives in reflective paint.

The task is carried out by boiling 6-aryl-2,2-dimethyl-4H-1,3-dioxin-4-ones (1A-g) with 2-methylene-1,3 .3m-trimethylindolenine (2), taken in the ratio 1:1 scheme:

The process is conducted at a temperature 108-110°C, and the solvent used absolute toluene.

The above set of essential features allows to obtain the following technical result is a straightforward way from the available materials received are not described in the literature with the organisations of the class 2-methylene-1,3 .3m-trimethylindolenine (Fischer indole), that exhibit fluorescent properties and can be used as products for the synthesis of new heterocyclic systems, as well as substances for sample labeling and additives for reflective paints.

From the patent and technical literature were not identified methods of obtaining (3Z)-4-aryl-4-hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)but-3-EN-2-ones having similar characteristics with the claimed method, and it has not been used for the original products, solvents in which the reaction takes place, and the temperature, on what basis is it possible to make a conclusion on the compliance of the claimed technical solution the patentability criteria of "novelty", "inventive step" and "industrial applicability".

The invention is illustrated by the following examples.

Example 1. (3Z)-4-Hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)-4-phenylbut-3-EN-2-he (3A).

A solution of 1.5 mmol of 2,2-dimethyl-6-phenyl-4H-1,3-dioxin-4-it (1A) and 1.5 mmol of indole Fisher (2) in 20 ml of absolute toluene was boiled 5 min, cooled, the precipitation of the compound (3A) was filtered. Yield 92%, TPL 184-186°C.

Found, %: C 78.82; N, 6.75; N, 4.20. C21H21NO2.

Calculated, %: C 78.97; H 6.63; N, 4.39.

Example 2. (3Z)-4-Hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)-4-(4-tolyl)but-3-EN-2-he (3b).

A solution of 1.5 mmol of 2,2-dimethyl-6-(4-tolyl)-4H-1,3-dioxin-4-it (1B) and 1.5 mmol of indole Fisher () in 20 ml of absolute toluene was boiled 10 min, cooled, the precipitation of the compound (3b) was filtered. Yield 89%, TPL 180-182°C.

Found, %: C 79.19; N, 6.95; N, 4.03. With22H23NO2.

Calculated, %: C 79.25; N, 6.95; N, 4.20.

Example 3. (3Z)-4-Hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)-4-(4-chlorophenyl)but-3-EN-2-he (3V).

A solution of 1.5 mmol of 2,2-dimethyl-6-(4-chlorophenyl)-4H-1,3-dioxin-4-it (1B) and 1.5 mmol of indole Fisher (2) in 20 ml of absolute toluene was boiled for 10 min, cooled, the precipitation of the compound (3b) was filtered. Yield 90%, TPL 172-173°C.

Found, %: C 71.17; H 5.75; N, 3.82. C21H20NO2Cl.

Calculated, %: C 71.28; H 5.70; N, 3.96.

Example 4. (3Z)-4-Hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)-4-(4-ethoxyphenyl)but-3-EN-2-he (3G).

A solution of 1.5 mmol of 2,2-dimethyl-6-(4-ethoxyphenyl)-4H-1,3-dioxin-4-it (1 g) and 1.5 mmol of indole Fisher (2) in 20 ml of absolute toluene was boiled 5 min, cooled, the precipitation of the compound (3 g) was filtered. Yield 88%, TPL 175-177°C.

Found, %: C 76.00; N, 7.13; N, 3.67. With23H25NO3.

Calculated, %: C 76.01; N, 6.93; N, 3.85.

In IR-spectra (vaseline oil) compounds (3A-g) are the bands of stretching vibrations enol group HE is involved in the formation of intramolecular hydrogen bonds (air force), in the form of a broad band in the region 3060-3085 cm-1, carbonyl group in position 2, participating in formation of the air force, in the form of a broad band in the region 1605-1610 cm-1.

In SPECT the Ah NMR 1N compounds (3A-g) in addition to the signals of the protons of aromatic rings and their associated groups are the singlet six protons of the two metal groups in position 3 indolinone fragment when in the field 1.72-1.73 ppm, a singlet of three protons of the methyl group in position 1 indolinone fragment in the field 3.29-3.32 ppm, a singlet proton group3N in the field 5.37-5.42 ppm, a singlet proton group1N in the field 6.34-6.45 ppm, broadened singlet proton enol group HE is in the field 17.39-17.55 ppm, related to the enol form And compounds (3A-g). In addition, in NMR spectra1H solutions of compounds (3A-g) in DMSO-d6there is a minor set of signals diketone form B: the signals of the protons of aromatic rings and related groups, a singlet six protons of two methyl groups at position 3 indolinone fragment in the area of 1.26-1.57 ppm, a singlet of three protons of the methyl group in position 1 indolinone fragment in the field of 3.13-3.22 ppm, a singlet of two protons groups3H2in the field 4.09-4.16 ppm, a singlet proton group1N in the field 6.09-6.19 ppm Spectral characteristics of compounds (3A-g) indicate their existence in DMSO-d6in the form of a mixture ketoenamine form a diketone and form B in the ratio of ~5:1.

The proposed method is simple, one-step and allows you to get undescribed in the literature is the temperature (3Z)-4-aryl-4-hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)but-3-EN-2-ones with a quantitative yield.

Example 5. Compounds (3A-g) in the solid state have stable fluorescence (emission in the field of yellow light at λ=580-595 nm) upon irradiation with a UV lamp at λ 254 nm. Fluorescence is retained during storage of the samples under normal conditions for a long time.

Optical activity of the proposed compounds can be used individually and in compositions for coating fluorescent labels, invisible under normal lighting, banknotes or documents requiring protection encoding.

Mixed with the dyes they can be used for the manufacture of fluorescent paints, glow, which is called the UV and short wavelength visible radiation.

From the description and practical application of the present invention to specialists will be obvious and other private forms of its implementation. The description and examples are considered to illustrate the invention, the essence of which and the scope of patent claims is defined in the following claims the set of essential features and their equivalents.

1. (3Z)-4-aryl-4-hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)but-3-EN-2-ones of General formula

2. A method of obtaining a (3Z)-4-aryl-4-hydroxy-1-(1,3 .3m-trimethylindolenine-2-ilidene)but-3-EN-2-ones of General formula

Hara is turizmisa fact, 6-aryl-2,2-dimethyl-4H-1,3-dioxin-4-ones is subjected to interaction with 2-methylene-1,3 .3m-trimethylindolenine in an environment of absolute toluene, followed by separation of the target product.

3. The method according to claim 2, characterized in that the process is conducted at a temperature 108-110°C.

4. The method according to claim 2, characterized in that the solvent used absolute toluene.



 

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where R is hydrogen, (C1-C6)alkyl, and the alkyl group optionally contains one phenyl substituent, which, in turn, optionally contains at least one Deputy, selected from the group comprising halogen, methoxy, ethoxy, (C1-C6)alkyl; R1means phenyl cycle containing at least one Deputy, selected from the group comprising (C1-C6)alkoxy, hydroxy, nitro, (C1-C6)alkoxycarbonyl one or fluorine, or R1represents the balance of the pyridine of the formula II

where the carbon atoms 2, 3 and 4 of the remaining pyridine optionally have the same or different substituents R5and R6and R5and R6denote (C1-C6)alkyl or halogen, or R1presents arylamination-2-methylprop-1-ilen group, or R and R1together with the nitrogen atom to which IGN="ABSMIDDLE">

where R7denotes phenyl or pyridinyl; R2means (C1-C6)alkyl, which optionally contains a phenyl residue, which, in turn, optionally substituted with halogen, methoxy group or ethoxypropane, or related to R2(C1-C6)alkyl group optionally substituted 2-, 3 - or 4-pyridinium residue; R3and R4are the same or different substituents and represent hydrogen, hydroxy, (C1-C6)alkoxy, (C1-C3)alkoxycarbonyl or (C1-C3)alkoxycarbonyl(C1-C3)alkyl, or R3is cyclopentanecarbonitrile; Z denotes Oh, and alkyl, alkoxy or alkylamino mean as an unbranched group, such as methyl, ethyl, n-propyl, n-butyl, n-hexyl and branched alkyl groups such as isopropyl or tert-butylene group; halogen means fluorine, chlorine, bromine or iodine and alkoxygroup means methoxy, propoxy, butoxy, isopropoxy, isobutoxy or phenoxypropan, and their pharmaceutically acceptable salts with acids

The invention relates to new hydroxyindole General formula

< / BR>
where R1- C1-C12-alkyl, linear or branched, if necessary monosubstituted monocyclic saturated or polyunsaturated carbocycles with 6 ring members, WITH6-aryl group and closed carbocyclic substituents on its part, if necessary, can be mono - or polyamidine R4; R5- monocyclic polyunsaturated carbocycles with 6 ring members, mono - or politeley atoms, halogen or a monocyclic polyunsaturated heterocycles with 6 ring members, one of which is N as heteroatom, mono - or politeley atoms of halogen; R2and R3can be hydrogen or HE, and at least one or both of the Deputy should be-HE; R4means-H, -OH, -F, -Cl, -J, -Br, -O-C1-C6-alkyl, -NO2; A -, or a bond, or -(CHOZ)m-(C= 0)-, and m= 0

The invention relates to new indole derivative of the formula I

< / BR>
in which R1is hydrogen, (NISS

The invention relates to derivatives of 2-phenylindole, mixtures of their isomers or individual isomers of General formula I, where R1is unbranched or branched C1-C8is alkyl or hydrogen; R2- the remainder of the formula CO-NH2or-CH2-OH

The invention relates to 1H-indol-3-acetamide General formula I where X is oxygen; R1selected from groups (i), (iii), where (i)6-C20-alkyl, C4-C12-cycloalkyl; (iii) - (CH2)n-(R80), where n is 1-8 and R80is the group specified in (i); R2is hydrogen, halogen, C1-C3-alkyl, C1-C2-alkylthio,1-C2-alkoxy; R3each independently is hydrogen or methyl; R4- R7each independently - C1-C10-alkyl, C2-C10alkenyl,3-C8-cycloalkyl,1-C10-alkoxy,

WITH4-C8-cycloalkane, phenoxy, halogen, hydroxy, carboxyl, -C(O)O(C1-C10-alkyl), hydrazide, hydrazino, NH2, NO2, -C(O)NR82R83where R82and R83independently is hydrogen, C1-C10-alkyl or a group of formula (a), where R84and R85independently is hydrogen, C1-C10-alkyl; p= 1 to 5; z is a bond, -O-, -NH-; Q is-CON(R82R83), -SO3H, phenyl, a group of formula b), C), (d), where R86independently selected from hydrogen, C1-C10-alkyl, and their pharmaceutically acceptable salts or their esters, or Amida

FIELD: organic chemistry, medicine, biochemistry.

SUBSTANCE: invention relates to novel compounds of indoline of the formula (I): , wherein R1 and R3 are similar or different and each means hydrogen atom (H), lower alkyl group or lower alkoxy-group; R2 means -NO2, -NHSO2R6 [wherein R means (C1-C20)-alkyl group, aryl group or -NHR7 (wherein R7 means H, -COR13 (wherein R13 means H, lower alkyl group) or lower alkoxycarbonyl group)], -NHCONH2 or lower alkyl group substituted with -NHSO2R6 [wherein R6 means (C1-C20)-alkyl group, aryl group or -NHR7 (wherein R7 means H, -COR13 (wherein R13 means H, lower alkyl group) or lower alkoxycarbonyl group)]; R4 means H, (C1-C20)-alkyl group optionally substituted with hydroxy-group, -COR13 (wherein R13 means H, lower alkyl group), lower alkenyl group, lower alkoxy-lower alkyl group, lower alkylthio-lower alkyl group, (C3-C8)-cycloalkyl group or (C3-C8)-cycloalkyl-(C1-C3)-alkyl group; R5 means (C1-C20)-alkyl group, (C3-C8)-cycloalkyl group or aryl group; R12 means H, lower alkyl group, lower alkoxy-lower alkyl group or lower alkylthio-lower alkyl group wherein aryl represents phenyl or naphthyl, or its pharmaceutically acceptable salt. Compounds possesses the strong inhibitory effect on activity of acyl-coenzyme A:cholesterol acyltransferase and the strong inhibitory effect on lipid peroxidation processes that allows its using as a component of pharmaceutical compositions.

EFFECT: valuable medicinal and biochemical properties of compound and pharmaceutical compositions.

31 cl, 5 tbl, 68 ex

Crystal habits // 2334738

FIELD: chemistry.

SUBSTANCE: invention concerns crystal habits of fluvastatin sodium salt hydrates referred to as polymorphic crystal habits C, D, E and F. Production method of these crystal habits, pharmaceutical composition for 3-hydroxy-3-methylglutaryl- coenzyme YMG-CoA inhibition based on these crystal habits C, D, E, F are described.

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8 cl, 6 dwg, 6 ex

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