Heterocyclic o-dicarbonitrile

 

(57) Abstract:

The invention relates to the field of production of new heterocyclic o-dicarbonitriles formula I

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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, 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. table 2.

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, scintillate the signal during transmission through 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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The claimed compounds are:

Acento [1,2-b]cinoxacin-9,10-dicarbonitrile (I):

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dibenzo[a,s]fenesin-11,12-dicarbonitrile (II):

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benzo[a]fenesin-9,10-dicarbonitrile (III):

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1,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanogenesis-7.8 dicarbonitrile (IV):

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oxohydroxides-2,3-dicarbonitrile (V):

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indolo[2,3-b]cinoxacin-8,9-dicarbonitrile (VI):

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2-phenyl-3-(2-thienyl)-6,7-inoxidizability(VII):

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2,3-diphenyl-6,7-hirel)-6,7-inoxidizability (X):

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These compounds obtained by condensation reaction of 4,5-diaminomaleonitrile with the corresponding diketone according to the scheme:

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The reaction is carried out in acetic acid medium at boiling point for 1...1.5 hours.

The invention is illustrated by the following examples.

Example 1. Into a flask equipped with reflux condenser, consistently load 30 ml of acetic acid, 1.6 g (0.01 mol) of 4,5-diaminomaleonitrile, 1.8 g (0.01 mol) acenaphthylene-1,2-dione. The reaction mixture was kept at boiling for 1.5 hours. Then the reaction was poured into 100 ml water, the precipitate is filtered off, washed with 50 ml of water and crystallized from DMF. Get 2,52 g (82.8% of theory) azento[1,2-b]cinoxacin-9,10-dicarbonitrile (I) - white crystalline powder with so pl. >300oC.

Found,%: C 78,90; N 2,69; N 18,37.

Calculated,%: C 78,93; N 2,66; N 18,41. C20H8N4< / BR>
1H NMR ([N] DMSO): , M. D.: 9,00 (s, 2H), 8,15 (d, 2H, J=8 Hz), of 7.70 (t, 2H), 7,43 (d, 2H, J=8,l Hz).

Examples 2-10. The reaction is carried out analogously to example 1, except that the reagent (acenaphthylene-1,2-dione), respectively, are used in equimolar quantities of 9,10-dihydro-9,10-phenanthroline, 1,2-dihydro-1,2-naphthalenamine, 1,2-di(4-bromophenyl)-1,2-atention, 1,2-di(2-furyl)-1,2-atention. The conditions and results of the synthesis are given in table. 1.

Example 11. Condensation of I with rhodamine 123. In a flask equipped with stirrer, thermometer, reflux condenser and capillary to enter argon, download 3.1 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 hours, then vacuum over P2O5. Obtain 5.9 g (93% of theory) of hexatriene.

Found,%: C 77,18; N 4,30; N 10,95.

Calculated,%: C 77,21; N 4,28; N 10,98. C82H54N10O6< / BR>
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 maximum of a spectrum of radiation - 458 410 and the 1, except that instead of phthalonitrile I used equimolar amounts of other phthalonitrile II - X.

The conditions and results of the syntheses and spectral characteristics of the received macroheterocycles are given in table.2.

Heterocyclic o-dicarbonitrile General formula

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