Aroylmethylene-2,4-dihydro-1h-3,1-benzoxazine-4-ones eliciting fluorescent property and method for their preparing

FIELD: organic chemistry.

SUBSTANCE: invention relates to new individual compounds of benzoxazine class and to a method for their preparing. Invention describes 2-aroylmethylene-2,4-dihydro-1H-3,1-benzoxazine-4-ones of the formula (I): wherein R means hydrogen atom (H) (a), -CH3 (b), -OCH3 (c), -OC2H5 (d), chlorine atom (Cl) (e) eliciting fluorescent properties and stable in UV-light. Also, invention a method for preparing abovementioned compounds. Proposed compounds elicit fluorescent properties and can be used as the parent substances for synthesis of new heterocyclic systems.

EFFECT: improved preparing method, valuable properties of compounds.

4 cl, 6 ex

 

The invention relates to the field of organic chemistry, namely to new individual compounds of the class of benzoxazines and method of production thereof, which exhibit fluorescent properties and can be used as products for the synthesis of new heterocyclic systems.

From the literature known to the closest analogues of the claimed compounds - derivatives of phenoxazine, in particular 2-aryl-4H-3,1-benzoxazin-4-ones (1), 2-(4-methoxyphenyl)-4H-3,1-benzoxazin-4-ones (2), 2-(2-totalminutes)-4H-oil-[2,3-d]-1,3-oxazin-4-ones (3), which has fluorescent properties. The method of obtaining data derived phenoxazine lies in the interaction of Anthranilic acid or substituted with acid chloride p-methoxybenzoic acid or p-toluenesulfonyl chloride (Bmikeandvicki and other Organic phosphors. - M., X., 1984, s-124).

The objective of the invention is to develop a simple, one-step retrieval method is not described in the literature 2-koimeterion-2,4-dihydro-1H-3,1-benzoxazin-4-ones, exhibiting fluorescent properties.

The task is carried out by boiling o-carboxanilido arealuxury acid (Ia-e) with dicyclohexylcarbodiimide in an inert aprotic solvent according to the scheme:

I, II: R=H (a), CH3(b), CH3About () 2H5O (g), Cl (l), Br (e).

The process is conducted at a temperature 82-84°and in an inert aprotic solvent used 1,2-dichloroethane.

Compounds (IIa-e) in the solid state have stable fluorescence (emission in the field of yellow light when λ=580-595 nm) upon irradiation with UV lamp λ 254 nm. Alcohol and chloroform solutions of the compounds (IIa-e) have no fluorescence. Fluorescence is retained during storage of the samples under normal conditions for a long time.

From the patent and technical literature were not identified ways to obtain 2-koimeterion-2,4-dihydro-1H-3,1-benzoxazin-4-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" and "inventive step".

The invention is illustrated by the following examples.

Example 1. 2-benzoylmethylene-2,4-dihydro-1H-3,1-benzoxazin-4-one IIa.

A solution of 0.95 g (3.35 mmol) of o-carboxanilide benzoyloxy acid (compound Ia) and 0.69 g (3.35 mmol) of dicyclohexylcarbodiimide in 20 ml of 1,2-dichloroethane is boiled for 1 hour, cooled, the precipitate of dicyclohexylamine filtered off, the mother liquor is evaporated, the OST is OK crystallized from propanol-2. Obtain 0.89 g (100%).

Compound IIa. With16H11MO3, TPL 141-142°C.

Found, %: C 72.39, H 4.15, N, 5.30.

Calculated, %: C 72.41, H 4.17, N 5.28.

Other compounds obtained similarly.

Compound IIb. 2-p-toluylene-2,4-dihydro-1H-3,1-benzoxazin-4-one.

Output 100% C17H13About3, TPL 178-179°C.

Found, %: C 73,10, N 4,67, N Of 5.03.

Calculated, %: C 73,11, N 4,69, N 5,01.

Compound IIb. 2-(4-methoxybenzylidene)-2,4-dihydro-1 H-3,1-benzoxazin-4-one.

Output 100%. C17H13NO4, TPL 164-165°C.

Found, %: C 69.17, H 4.46, N, 4.75.

Calculated, %: C 69.15, H 4.44, N 4.74.

Connection G. 2-(4-ethoxybenzylidene)-2,4-dihydro-1H-3,1-benzoxazin-4-one.

Output 100%. C18H15NO4, TPL 165-166°C.

Found, %: C 69,90, N 4,88, N 4,55.

Calculated, %: C 69,89, N 4,89, N 4,53.

Connection D. 2-(4-chlorobenzylidene)-2,4-dihydro-1H-3,1-benzoxazin-4-one.

Output 100%. With16H10ClNOC, TPL 204-205°C.

Found, %: C 64.10, H 3.34, Cl 11.85, N 4.68.

Calculated, %: C 64.11, H 3.32, Cl 11.83, N 4.68.

Compound IIe. 2-(4-bromobenzonitrile)-2,4-dihydro-1H-3,1-benzoxazin-4-one.

Output 100%. C16H10BrNO3, TPL 204-205°C.

Found, %: C 55,83, H 2.95, Br 23,25, N 4.05.

Calculated, %: C 55,84, N 2,93, Br 23,22, N 4,07.

Compounds (IIa-e) - pale yellow crystalline substances, soluble in acetone, chloroform, 1,2-dichloroethane, dimethylsulfoxide is, poorly soluble in alkanes, alcohols, insoluble in water. Stable when stored under normal conditions.

In the IR spectra of compounds (IIa-e)taken in vaseline oil, there is an absorption band of the lactone carbonyl group benzoxazinones cycle in the field 1758-1768 cm-1and broad absorption band ketone arolina groups involved in the formation of intramolecular hydrogen bonds N-chelate-type region 1630-1635 cm-1.

In the PMR spectra of the compounds (IIa-e)taken in deuterated chloroform, in addition to the group of signals of aromatic protons and proton signals of the substituents R are the singlet proton of NH group in the field 14.24-14.27 ppm and the singlet of the vinyl proton in the field 5.88-5.92 ppm

The proposed method is simple, one-step and allows you to get undescribed in the literature 2-koimeterion-2,4-dihydro-1H-3,1-benzoxazin-4-ones with a quantitative yield.

1. 2-Koimeterion-2,4-dihydro-1H-3,1-benzoxazin-4-ones of General formula

R=H (a), CH3(b), CH3About (),

With2H5O (g), Cl (l), Br (e)

exhibiting fluorescent properties.

2. The method of obtaining 2-koimeterion-2,4-dihydro-1H-3,1-benzoxazin-4-ones according to claim 1, characterized in that on-carboxanilide kolokani acid is subjected to interaction with dizick what hexylberberine in inert aprotic solvent, followed by separation of the target product.

3. The method according to claim 2, characterized in that the process is conducted at a temperature 82-84°C.

4. The method according to claim 2 and 3, characterized in that an inert aprotic solvent used 1,2-dichloroethane.



 

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