The method of obtaining dibenzo (b,e)pyrano(3,2-b)-1 - benzopirilievyh salts

 

(57) Abstract:

The described method of obtaining compounds of General formula (1),

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where X = 0; R1= a hydrogen atom; R2, R3, R4= a hydrogen atom or halogen, C1-C6alkyl or C1-C6alkoxygroup, the nitro-group; R4, R6, R7= hydrogen or C1-C6alkyl; with high fluorescence characteristics and used for dyeing aminomethylating fibers and as fluorescent dyes, namely, that 2-R2-5,5-R6, R7-cyclohexane-1,3-diodes enter into interaction with substituted or unsubstituted salicylic aldehydes in the presence of perchloric acid and triethylorthoformate.

Given: N; R1, R2, R3, R4, R5, R6, R7; Output (%); So square (oC);

1A; H, H, H, H, H, CH3CH3; 54.6; 294-297;

1B; H, OCH3, H, H, H, CH3CH3; 58.5; 303-305;

1B; H, NO2, H, H, H, CH3CH3; 42.0; 312-315;

1G; H, Br, H, H, H, CH3CH3; 71.3; 281-284;

1D; H, CH3, H, H, H, CH3CH3; 47.7; 272-273;

1E; H, H, CH3, H, H, CH3CH3; 52.3; 277-278;

1G; H, Br, H, Br, H, CH3CH3; 68.1; 314-315;

1H; H, Br, OCH31 table.

The invention relates to a new method of obtaining the previously described connections of a number of dibenzo[b, e]pyrano[3,2-b]-1-benzopirilievyh salts of General formula (I),

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where X 0;

R1a hydrogen atom;

R2-R4the atom of hydrogen or halogen, C1-C6alkyl or C1-C6alkoxygroup, the nitro-group;

R5, R6, R7the atom of hydrogen or C1-C6alkyl,

that exhibit fluorescent properties and are used as dyes for dyeing films and aminomethylating fibers (DOS 2942931 (1980), BASF, Erf. R. Schmidt, V. Koch; C. A. 95, 117065 (1980)).

A method of obtaining compound (I) (DOS 2942931 (1980), BASF, Erf. R. Schmidt, V. Koch; C. A. 95, 117065 (1980)) lies in the interaction of cyclic 1,3-diketones (II) with sodium hydride in a nitrogen atmosphere at 0oC in excess of HMPA (hexamethylphosphorotriamide, hexameter), the processing resulting from the deprotonation of sodium salt of 1,3-diketone (ketoenol) (III) butyllithium in hexane at 20oC, by heating with sodium salt of o-oxybenzaldehyde (IVa, X 0) in excess of hexadecapole, and with perchloric acid.

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where R1-R7X have the above for formula 1.

The disadvantage of this method is a Ki oC, the use of flammable reagents (sodium hydride, utility) and solvent (hexane), the use of a large number (up to 500 g per 5 g of the target product) hexadecapole and low yields of the target product (10-15%).

The aim of the invention is to obtain the previously described connections of a number of dibenzo[b, e] pyrano-(thiopyrano)[3,2-b] -1-benzo-prelievi- (thiapyrilium) salts of General formula 1 which exhibit fluorescent properties and are used as fluorescent dyes for aminomethylating fibers, simpler and more secure way (replacement of sodium hydride, utility on safer reagents, reduction and replacement of flammable and toxic solvents) and increased output connections 1.

The aim is achieved in that in the known method of producing compounds of the number of dibenzo[b,e]pyrano-(thiopyrano)-[3,2-b]-1-benzo-prelievi(thiapyrilium) perchlorates, including the interaction of the sodium salts of o-hydroxy(mercapto)benzaldehyde sodium salts 2-R5-5,5-R6,R7-cyclohexane-1,3-dione in the presence of perchloric acid, the difference is that as substituted o-hydroxy(mercapto)benzaldehyde use of compounds of General formula VI, as a 2-R5

A method of obtaining compound 1 is that 2-R5-5,5-R6, R7-cyclohexane-1,3-dione of General formula II is administered in cooperation with unsubstituted or substituted o-hydroxy(mercapto)benzaldehyde General formula VI in the presence of perchloric acid and triethylorthoformate. The latter is taken in excess is sufficient for the reaction, and also to absorb the water produced in the reaction and the water contained in perchloric acid.

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where R1-R7X have the above values for compounds of General formula 1.

The method of obtaining compounds 1 involves an inventive step, because the possibility of their receipt in the presence of triethylorthoformate and perchloric acid in such mild conditions is not obvious.

Has not been previously studied the combined effect of triethylorthoformate and perchloric acid in a mixture of o-hydroxy(mercapto)benzaldehyde and cyclic 1,3-diketones.

It is known that under the action of triethylorthoformate and perchloric acid on the fatty-aromatic ketones series, by condensation of two molecules of ketone with orthoevra formed 1,5-diketone, which in the reaction cyclized in Pillay cation (VII).

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(G. N. Dorofeenko In. A. Tkachenko, Zhur.org.chem., 10, 2188-2191, 1972).

Not containing terminal methyl groups of the 1,3-diketones of X under the action of triethylorthoformate and perchloric acid form cations 1,3-diethoxypropane (XII).

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(E. P. Olekhnovich, I. C. Box, Zhur.org.chem., 26, 213-214, 1990).

Action triethylorthoformate and perchloric acid in a mixture of o-hydroxy-(mercapto)benzaldehyde and cyclic 1,3-diketones undescribed.

Example 1. Getting perchlorate 6H-13,13-dimethyl-13H(dibenzo[b,e]-piano)[3,2-b]benzopyrene (1A).

The reaction mixture is in a ratio of 1.4 g (0.01 mol) of 5,5-dimethylcyclohexane-1,3-dione, 20 ml triethylorthoformate, 1.5 ml of 70% perchloric acid and 2.5 g (0.02 mol) of salicylic aldehyde is heated to 60oC for 5 min, cooled and incubated for 1 h the crystals formed are filtered and washed on the filter with ethyl acetate (2 times 5 ml) and ether (2 x 5 ml). Output: 2.24 g (54,6%), So pl. 294-297oC (decomp).

Example 2. Getting perchlorate 2,2-dimethoxy-6H-13,13-dimethyl-13H(dibenzo[b,e]pyrano)[3,2-b]benzopyrene (1B).

Get analogously to example 1 from 1.4 g (0.01 mol) of 5,5-dimethylcyclohexane-1,3-dione, 20 ml triethylorthoformate the AZL).

Example 3. Getting perchlorate 2,2-dinitro-6H-13,13-dimethyl-13H(dibenzo[b,e]pyrano)[3,2-b]benzopyrene (1B).

Get analogously to example 1 from 1.4 g (0.01 mol) of 5,5-dimethylcyclohexane-1,3-dione (II), 20 ml of triethylorthoformate, 1.5 ml of 70% perchloric acid and 3.4 g (0.02 mol) of n-nitrocellulose aldehyde. Yield: 2.1 g (42,0%), So pl. 312-313oC (decomposition).

Example 4. Getting perchlorate 2,2-dimethyl-6H-13,13-dimethyl-13H(dibenzo[b, e]pyrano)[3,2-b]-1-benzopyrane (1D)

The reaction mixture is in a ratio of 1.4 g (0.01 mol) of 5,5-dimethylcyclohexane-1,3-dione (II), 20 ml of triethylorthoformate, 1.5 ml of 70% perchloric acid and 2.7 g (0.02 mol) of n-methylolacrylamide aldehyde is heated before boiling (60oC) and boiled for 5 minutes to Cool, after 1 h, the crystals formed are filtered and washed on the filter with ethyl acetate (2 times 5 ml) and ether (2 x 5 ml). Yield: 2.1 g (47,7%), So pl. 272-273oC (from ice. CH3COOH).

Elemental analysis data of the compounds (1A-d) obtained in examples 1-4 are shown in table. Also the table shows the outputs, melting point and elemental analysis data of the compounds (1E) having the substituents in positions R2-R4received likewise the compounds (1A-d) (examples 1-4).

Rastvornoj orange-red fluorescence.

Thus, compounds of General formula (1) are more simple way than proposed to receive them earlier. The outputs of the compounds (1A) comprise 40-70%

1. R1=H; R5=H; R6=R7=CH3; x=0.

2. 1A: R2-R4= H; 1B: R2=OCH3; R3=R4=H; 1B: R2=NO2, R3=R4=H; 1G: R2=Br, R3= R4= H; 1D: R2=CH3, R3=R4=H; 1E: R2=R4=H, R3=CH3; 1G: R2=R4=Br, R3=H; 1Z: R2=R4=Br, R3=OCH3; 1i: R2=CH3, R3=NO2, R4=H.

3. Compound 1B: N Content Found 5.51; Calculated 5.57.

4. Compound 1G: Given joint (BrCl) halogen content.

5. Compound 1G: Given joint (BrCl) halogen content.

6. Connection 1Z: Given joint (BrCl) halogen content.

7. Compound 1i: N Content Found 5.19; Calculated 5.28.

8. The solvent for crystallization: 1A, b, W and nitromethane; 1D,e - CH3COOH; 1B,g presideny of nitromethane ether.

The method of obtaining dibenzo[b,e]pyrano[3,2-b]-1-benzopirilievyh salts of General formula I

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where X is O;

R1hydrogen;

R2, R3
R5, R6, R7hydrogen or C1- C6-alkyl,

including the interaction of substituted 2-R5, 5-R6, R7-cyclohexane-1,3-diones with o-oxybenzaldehyde in the presence of perchloric acid, characterized in that substituted 2-R5, R7-cyclohexane-1,3-diones used as a compound of General formula II

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where R5R7have the specified values,

and as o-oxybenzaldehyde use of substituted or unsubstituted salicylic aldehydes of General formula III

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where R1R4and X have the above values,

and the process is conducted in the additional presence of triethylorthoformate.

 

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