Heterocyclic o-dicarbonitrile

 

(57) Abstract:

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

where Ph =

o-Dicarbonitrile can be used to obtain hexatriene-fluorophores as a fragment of the donor to obtain hexatriene-bifluorophors besed and hexatriene-trifluoroprop, which are used as active media in liquid and solid lasers, scintillators, 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, especially for indication of hard radiation, TRANS is m communication 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. So 30, No. 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

where

The claimed compounds are

3-phenyl[1,2,4]triazolo[3,4,-b][1,3]benzothiazole-6,7-dicarbonyl (I):

3-[3,5-di(tertbutyl)phenyl][1,2,4]triazolo[3,4-b][1,3]benzothiazole-6,7-dicarbonitrile (II):

3-(4-bromophenyl)[1,2,4]triazolo[3,4-b][1,3]benzothiazole-6,7-dicarbonitrile (III):

The connection data is obtained by reaction of aromatic nucleophilic substitution of the bromine atom and the nitro group in 4-bromo-5-nitrophthalonitrile the corresponding bifunctional nucleophile, obrazuyutsya carried out in DMF in the presence of potassium carbonate at a temperature of 130...140 C for 2 h

The invention is illustrated by the following examples.

Example 1. To 20 ml of DMF under stirring was added 2.52 g (0.01 mol) BPN and 1.77 g (0.01 mol) of 5-phenyl-4H-1,2,4-triazole-3-thiol. After dissolution of the reagents to the reaction mixture at a temperature of 130C and vigorous stirring was added 4.14 g (0.03 mol)2CO3. The resulting mixture was stirred for 120 minutes Then the reaction mass was poured into 50 ml of water. Falling precipitate was filtered off, washed with 50 ml of water and recrystallized from a mixture of 2-propanol with DMF.

Get 2.25 g (75% of theory) of 3-phenyl[1,2,4]triazolo[3,4-b][1,3]benzothiazole-6,7-dicarbo-nitrile (I). It is a yellow crystalline powder, MP.>300C.

Found, %: C 63.59; H 2.33; N 23.30; S 10.66.

Calculated, %: C 63.78; H 2.34; N 23.34; S 10.64.

C16H7N5S

1H NMR ([N] DMSO):, M. D.: 9.00 (s, 2H), 8.65 (s, 1H), 8.10 (d, 2H, J=8),7.60 (m, 3H).

Example 2-3. The reaction is carried out analogously to example 1, except that the reagent 5-phenyl-4H-1,2,4-triazole-3-thiol are used, respectively, 5-[3,5-di(tertbutyl)phenyl]-4H-1,2,4-triazole-3-thiol and 5-(4-bromophenyl)-4H-1,2,4-triazole-3-thiol. Conditions and results of the synthesis are presented in table. 1.

Example 4. Condensation of I with rhodamine 123. In a flask equipped with stirrer, read the 0 g of phenol. The resulting mixture was slowly heated with stirring to 175...S. 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=60C for 2 hours, then vacuum over P205. Receive 5.99 g (95% of theory) of hexatriene.

Found, %: C 70.25; N, 3.52; N, 13.30; S 5.09.

Calculated, %: C 70.46; N, 3.52; N, 13.33; S 5.08.

(C74H44N12S2)

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

The structural formula of hexatriene derived from I and rhodamine 123

Macroheterocycles derived from I and rhodamine 123 has the following spectral characteristics: the maxima of the spectrum of radiation - 526, 567, 610 nm at the maxima of the absorption spectrum of 340, 465, 534 nm.

Example 5-6. The reaction is carried out analogously to example 4, except that instead of phthalonitrile I used equimolar amount of phthalonitrile II-III.

Conditions and results of the synthesis and spectral characteristics of the received macroheterocycles p is ptx2">where Ph



 

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