3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate [1,2-a] pyrimidines, exhibiting fluorescent properties, and method of production thereof

 

(57) Abstract:

The invention relates to the field of organic chemistry, namely to new individual compounds of class imidazopyridines, method of production thereof, which exhibit fluorescent properties and can be used as starting products for the synthesis of new heterocyclic systems, as well as substances for sample labeling and additives for reflective paints. Describes the 3-alkoxy-3(2-aryl-2-oxoethyl)-2,3(dihydro-2-accomidate /1,2-a/ pyridine formula I, where R2=CH3, R1=N(a), CH3(b), CH3O(b) Cl(g), Br(l), R2=C2H5, R2=H(e), CH3(W), Br(C), exhibiting fluorescent properties, which are stable in UV light. Also described is a method of obtaining the above-mentioned compounds. 2 S. and 4 C.p. f-crystals.

The invention relates to the field of organic chemistry, namely to new individual compounds of class imidazopyridines, method of production thereof, which exhibit fluorescent properties and can be used as starting products for the synthesis of new heterocyclic systems, as well as substances for sample labeling and additives for reflective trasteverini personality, passports with use of 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, for example, under the action of ultraviolet radiation (see U.S. patent N 4175776, IPC B 42 D 15/00, priority 27.11.78 year). However, the range of these colors at the present time.

Know the use of special paints containing reflecting the substance and, if necessary, aluminum powder (see U.S. patent N 4066280 IPC B 42 D 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.

From the patent literature known structural analogues of the claimed compounds tizanidine derivative imidazo [1,2-a] pyridine (Japan's bid N 228174, IPC C 07 D 471/02, 1990, Rehim,1991. 189 P) used as substances suppress the appetite, substances inhibiting the secretion of acid in the stomach.

Structural analogues exhibiting fluorescent properties not identified.

The method of obtaining trisemester or C4-C6alkenyl; R1-lower alkyl

The disadvantages of this method is its multi-stage and duration. In addition, this way it is impossible to obtain 3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate [1,2-a] pyridine exhibiting fluorescent properties.

The objective of the invention is to develop a simple, one-step retrieval method is not described in the literature 3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate [1,2-a] pyridines, exhibiting fluorescent properties, as well as the expansion of the means, are used as labels to protect documents from unauthorized copying and additives in reflective paint.

This object is achieved by the interaction of diazoalkanes with 2 Piritramide 4-aryl-2,4-dioxobutane acid (1 a-d) in a mixture of inert solvents according to the scheme:

< / BR>
I, R1=H (a), CH3(b), CH3O (b) Cl (g), Br (e);

II, R2=H, R1= N (a), CH3(b), CH3O (b) Cl (g), Br (e);

R2=CH3, R1=H (e), CH3(W), Br (C).

The process is preferably carried out at a temperature of -5 to +5 degrees C, and as the inert solvent used chloroform or toluene.

Compounds 11 (a-C) have the s to 1.5 μg/ml, alcohol - 1 mg/ml, chloroform - mcg/ml upon irradiation with a UV lamp at 254 nm. Fluorescence is retained during storage of the samples under normal conditions for a long time.

Compounds 11 (a-C) are used as substances for labeling, coding documents with subsequent detection using ultraviolet radiation, and also as additives for reflective paints.

From the patent and technical literature were not identified methods for the preparation of 3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate [1,2-a] pyridines having similar characteristics with the claimed method, namely, not 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" and "inventive step".

The invention is illustrated by the following examples.

Example 1. 3-methoxy-3-(2-phenyl-2-oxoethyl)-2,3-dihydro-2-accomidate [1,2-a] pyridine.

To a solution of 2.68 g (0.01 mol) of 2-pyridylamine 4-phenyl-2,4-dioxaborinane acid (compound 1) in 50 ml of chloroform at -5 to+5 degrees With add a solution of 0.84 g (0.02 mol) of diazomethane 30 is jut from benzene. Get 1,31 g (47%). Connection 11 a.C16H14N2ABOUT3so different. 197 - 197,5 deg C.

found,%: C 68,17, H is 4.85, N 10,11.

calculated,%: C 68,08, H 5,00, N 9,92.

Example 2. 3-methoxy-3-[2-(4-were)-2-oxoethyl] -2,3-dihydro-2-accomidate [1,2-a] pyridine.

To a solution 2,82 g (0.01 mol) of the compound (1B) in 50 ml of toluene at - 5+5 degrees With add a solution of 0.84 g (0.02 mol) of diazomethane in 30 ml of diethyl ether and reactional the mixture is stirred for 6 hours the precipitation is filtered off and recrystallized from benzene, to obtain 1.42 g (48%).Connection 11 b. C17H16N2O3so different. 201,5-203 hail

found,%: C 68,77, H ceiling of 5.60, N 9,51

calculated,%: C 6891, H 5,44, N 9,45.

Example 3. 3 ethoxy-3-(2-phenyl-2-oxoethyl)-2,3-dihydro-2-accomidate [1,2-a] pyridine.

To a solution of 2.68 g (0.01 mol) of the compound (1A) in 50 ml of chloroform at -5 to+5 degrees With added 1.12 g (0.02 mol) of diazoethane in 30 ml of diethyl ether and the reaction mixture is stirred for 4 hours the Solvent is removed, the residue is recrystallized from benzene. Obtain 1.27 g (43%). Connection 11 e, C17H16N2ABOUT3so different. 194-196 deg C.

found,%: C 69,05, H 5,49, N 9,31.

calculated,%: C 68,91, H 5,44, N 9,45.

Example 4. 3 ethoxy-3-[2-(4-bromophenyl)-2-oxoethyl]5 degrees With add a solution of 1.12 g (0.02 mol) of diazoethane in 30 ml of diethyl ether and the reaction mixture is stirred for 4 hours The solvent is removed, the residue is recrystallized from benzene. Get 1,69 g (45%). Compound 11 C. C17H15BrN2O3so different.194-195 deg C.

found,%: C 54,25, H a 3.87, 21,49, N 7,32.

calculated,%: C 54,42, H 4,03, 21,30, N 7,47.

Other compounds obtained similarly.

The connection of the 11th century 3-methoxy-3-[2-(4-methoxyphenyl)-2-oxoethyl]- 2,3-dihydro-2-accomidate [ 1,2-a ] pyridine.

Yield 43%. CHNO so different. of 174.5-176 deg C.

found,%: C 65,19, H 5,27, N is 9.09.

calculated,%: C, compared with 65.38, H 5,16, N 8.97.

The connection 11, 3-methoxy-3[2-(4-chlorophenyl)-2-oxoethyl]-2,3-dihydro-2-accomidate [1,2-a]pyridine.

Yield 39%. C16H13CN2O3so different. 207-208 hail

found,%: C 60,44, H 4,25, C of 11.26, N 8,70.

calculated,%: C 60,67, H4,14, C 11,19, N 8,84.

The connection 11. 3-methoxy-3-[2-(4-bromophenyl)-2-oxoethyl]-2,3-dihydro-2-accomidate [1,2-a] pyridine.

Yield 32%. C16H13rN2ABOUT3so different. p.223-224 deg C.

found,%: C 53,30, H 3,81, 22,32, N to 7.59.

calculated,%: C 53,21, H 3,63, B 22,12, N 7,76.

Connection 11 W. 3 ethoxy-3-[2-(4-were)-2-oxoethyl]-2,3-dihydro-2-accomidate [1,2-a]pyridine.

Yield 25%. C18H18N2ABOUT3so different. 187 deg C.

In the IR spectra of compounds 11 (a-C), taken in vaseline oil, there is an absorption band of the carbonyl group of the imidazole cycle in the field 1725-1701 cm, the absorption band of ketone carbonyl in the field 1685-1650 cm-broadened absorption band of the relations C=N and C=C in the field 640-1623 see

In the PMR spectra of compounds 11(a-d), taken in deuterated chloroform, in addition to the group of signals of aromatic protons and the pyridine ring with center at 7,22-7,65 M. D., and signals of the substituents R, there is a singlet protons of a methyl group when is 3.08-3.15 in M. D. and singlet protons of methylene group at 3,66-3,83 M. D.

The PMR spectra of compounds 11 (e-h) are characterized by the presence of a group of signals of the pyridine protons of the aromatic rings with at 7.55 - a 7.85 memorial plaques, and the signals of the protons of the substituents R. also present in the spectra of the triplet proton metal group when 1,11 M. D. and multiplet, protons of methylene group at 3,26-3,55 memorial plaques characteristic of ethoxyline Deputy, and the singlet protons of methylene groups present at 3,71-3,78 M. D.

The selected temperature is at temperatures above +5 degrees To evaporate from the reaction mixture of gaseous diazoalkanes.

The proposed method is simple, one-step and allows you to get undescribed in the literature 3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate [1,2-a]pyridine.

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.

The nature of fluorescence (studies in the field of blue light at a = 430 440 nm) makes it possible to use these compounds as optical brighteners for whitening natural and synthetic fibers, paper, plastics).

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.

1. 3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate[1,2-a]pyridine General formula

< / BR>
R2=CH3, R1=H(a), CH3(b), CH3O(b) Cl(g), Br(e);

R2=C2H5, R1=H(e), CH3(W), Br(C).

exhibiting fluorescent properties.

2. 3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate[1,2-a]pyridine ofiolitovogo radiation.

3. 3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate[1,2-a]pyridine General formula, as in point 1, as additives for svetootrazauschii colors.

4. Method for the preparation of 3-alkoxy-3-(2-aryl-2-oxoethyl)-2,3-dihydro-2-accomidate[1,2-a]pyridines of General formula

< / BR>
R2=CH3, R1=H(a), CH3(b), CH3O(b) Cl(g), Br(e);

R2=C2H5, R1=H(e), CH3(W), Br(C).

characterized in that 2-pyridylamine 4-aryl-2,4-dioxobutane acids are subjected to interaction with diazoalkane in an inert solvent, followed by separation of the desired products.

5. The method according to p. 4, wherein the process is conducted at a temperature (-5) - (+5)oC.

6. The method according to PP.4 and 5, characterized in that as the inert solvent used chloroform or toluene.

 

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