Heterocyclic o-dicarbonitrile

 

(57) Abstract:

Describes new heterocyclic o-dicarbonitrile formula I

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where R is hydrogen, phenyl, naphthyl or chinosol. These compounds may be used to obtain hexatriene-fluorophores, as a fragment of the donor to obtain hexatriene-bifluorophors besed and hexatriene-trifluoroprop. Such hexatriene promising for use as active media of liquid and solid lasers, scintillators, especially for indication of hard radiation, for the transformation of shortwave radiation in the long wavelength in the transmission of information through fiber-optic communication lines, to increase the power of solar panels for protection of securities, for the manufacture of billboards etc., 2 tab.

The invention relates to the field of production of new heterocyclic o-dicarbonitriles. o-Dicarbonitrile can be used to obtain hexatriene-fluorophores, as a fragment of the donor to obtain hexatriene-bifluorophors besed and hexatriene-trifluoroprop. Such hexatriene promising for use as active media of liquid and solid lasers, scintillators, CCA is areduce information on fiber-optic communication lines, to increase the power of solar panels for protection of securities, for the manufacture of billboards, etc.

Know the use of phthalonitrile together with the unsubstituted rhodamine to obtain hexatriene (Sealing C. A., Feofanov B. N., Lambs N.N. and other Polyhexamethylene based heterocyclic diamines. // Polymer sciense ser. Conn. B. 1988, T. 30, 4, S. 286-291).

This hexatrien has the following spectral characteristics: band emission 540 nm when excited in the band 312 nm.

The problem solved by the present invention is the obtaining of new heterocyclic o-dicarbonitriles.

Come heterocyclic o-dicarbonitrile General formula:

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where R is

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To saleemi compounds include: 1H-1,2,3-benzotriazol-5,6-dicarbonitrile (I):

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1-phenyl - 1H-1,2,3-benzotriazol-5,6-dicarbonitrile (II):

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1 -(1-naphthyl)- 1H-1,2,3-benzotriazol-5,6-dicarbonitrile (III):

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1 -(8-chinolin)- 1H-1,2,3-benzotriazol-5,6-dicarbonitrile (IV):

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1 -(5-chinolin)-1H-1,2,3-benzotriazol-5,6-dicarbonitrile (V):

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The connection data is obtained by reaction of diazotization of N-R-4,5-diaminomaleonitrile with subsequent cyclization according to the scheme:

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Example 1. To 30 ml of 50% acetic acid add 1,58 g (0.01 mol) of 4,5-diaminomaleonitrile. Then to the resulting suspension under vigorous stirring in one step add to 0.69 g (0.01 mol) of sodium nitrite, pre-dissolved in 5 ml of water. The resulting mixture was heated to 60oC and maintained at this temperature for 0.5 h, After cooling to room temperature the precipitate is filtered off, washed with 50 ml of water and crystallized from ethanol.

Get 1.4 g (83.1% of theory) 1H-1,2,3-benzotriazol-5,6-dicarbonitrile. It is a yellow crystalline powder, TPL237-239oC.

Found, %: C 56.78 Has; N 1,82; N 41,34.

Calculated, %: C 56,80; N 1,79; N 41,41; C8H3N5.

1H NMR ([N] DMSO): , M. D.: 14,70 (s, 1H), cent to 8.85 (s, 2H).

Examples 2 to 5. The reaction is carried out analogously to example 1, except that the reagent (4,5-diaminomaleonitrile) respectively are used equimolar amounts of N-phenyl-4,5-diaminomaleonitrile, N-(1-naphthyl)-4,5-diaminomaleonitrile, N-(8-chinolin)-4,5-diaminomaleonitrile, N-(5-chinolin)-4,5-diaminomaleonitrile. The conditions and results of the synthesis are presented in table. 1.

Example 6. Condensation of I with redominant 1.7 g (0.01 mol) I, 3.8 g (0.01 mol) of rhodamine 123 and 10 g of phenol. The resulting mixture was slowly heated with stirring to 175-185oC. the Resulting melt is maintained with stirring in a stream of argon prior to the termination of excretion of ammonia. After the reaction, the reaction mixture was poured into 20 ml of ethanol, and the precipitated precipitate is filtered off, washed with 3 ml of ethanol and dried at T=60oC for 2 h, and then in vacuum over P2ABOUT5. Obtain 4.6 g (93% of theory) of hexatriene.

Found, %: C 69,83; N 3,66; N Ls 16.80.

Calculated, %: C 69,86; N. Of 3.65; N 16,86 (C58H36N12O6).

The IR spectrum of hexatriene no band 2220 cm-1-CN, there is a band at 680 cm-1- C=N-.

The structural formula of hexatriene derived from I and rhodamine 123:

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Macroheterocycles derived from I and rhodamine 123 has the following spectral characteristics: the maxima of the spectrum of radiation - 433 and 502 nm at the maxima of the absorption spectrum - 316 and 361 nm.

Examples 7 to 10. The reaction is carried out analogously to example 6, except that instead of phthalonitrile I used equimolar amounts of other phthalonitrile II - V.

The conditions and results of the synthesis, as well as the ski on-dicarbonitrile General formula

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where

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1 cl, 1 ex, 2 tbl

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2 tbl, 1 ex

FIELD: synthesis of lubricant oiliness addends.

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.

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2 tbl, 1 ex

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14 cl, 14 tbl, 24 ex

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1 cl, 4 dwg, 5 ex

FIELD: chemistry.

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8 cl, 7 tbl, 633 ex

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5 cl, 7 ex

FIELD: chemistry.

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EFFECT: high effectiveness of application.

10 cl, 384 ex

FIELD: chemistry.

SUBSTANCE: described is a novel compound - 1-acetyl-5,10-dioxy-5,10-dihydro-2H-anthra[2,3-D][1,2,3]triazole-7,8-dicarboxylic acid of formula , which can be used as a starting compound in synthesis of metal complexes of tetra[4,5]([6,7]1-acetyl-2H-naphtho[2,3-D][1,2,3]triazole-5,8-dione)phthalocyanine.

EFFECT: possibility of use as dyes or catalysts.

1 cl, 3 ex, 4 dwg, 1 dwg

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