SU1608191A1 - Method of producing 1,3,3-trimethylindolino-2-spiro-2ъ-[2n]selenopyrano [5,6-d]pyrazol - Google Patents

Abstract

The invention relates to derivatives of heterocyclic substances, in particular the preparation of 1,3,3-trimethylindoline-2-spiro-2 ¹ - [2H] selenopyrano [5,6-D] pyrazole, which can be used as a solid-phase photochromic material for optical recording of information on laser discs. The goal is to develop a new way of obtaining a valuable substance. For this purpose, thermal spraying of 1 - [(1,3,3-trimethylindolidene-2) ethylidene] -1-phenyl-3-isopropyl-pyrazolin-2-ylidene-4-selenone-5 onto a substrate in vacuum at 10 ^-6 ≤ P≤2 ^. 10 ^-5 Torr and 400-450 ° C. 95% yield

Gross f-la: C ₂₅ H ₂₇ N ₃ SE.

Description

The invention relates to the chemistry of heterocyclic compounds of selenium, specifically to a new method for producing 1,3,3-trimethylindolin-2-spiro2 ¹ -pH] selenopyrano-p, 6-cG] pyrazole of the formula

(54) METHOD FOR PRODUCING 1,3,3-TRIMETHYLINDOLIN-2-SPIRO-2'- [2H] SELENOPIRANO [5, b-d] PYRAZOL (57) The invention relates to derivatives of heterocyclic substances, in particular to the preparation of 1,3,3 -trimethylindolin-2-spiro-2 '- [2Н ^ selenopyrano [5,6sprpirazole, which can be used as a solid-phase photochromic material for optical recording of information on laser discs. The goal is to develop a new method for producing a valuable substance. To do this, conduct thermal spraying of 1 - £ (1,3,3-trimethylindolidene-2) ethylidene ^ -1-phenyl-Zizopropyl-pyrazolin-2-ylidene-4-selenone-5 onto a substrate in vacuum at 10 ^_ί έ Р έ 2 1 0 ~ ⁵ torr and 400-450 ° С. Yield 95%; gross flag: C ₂₅ H ₂₇ N _d Se.

The aim of the invention is to develop a new method for producing the compounds of formula (I) in the solid phase in the form of a film, which allows it to be used as a photochromic compound.

This goal is achieved by conducting a thermal spraying process of 1- [X1,3,3-trimethylindoliden-2) ethylidene ^ -1-phenyl-3-isopropylpyrazolin-2-ideey-4-selenone-5 (II) on a substrate in vacuum at 10 * ⁶ ^ Ρέ2χ хУ '^ torr and a temperature of 400-450 ° С.

Example). Synthesis of 1 ^ (1,3,3trimethylindolide n-2) -ethylidene] -1-phenyl-3-isopropyl-pyrazolin-2-ylidene-4-selenone-5 (open-chain merocyanine isomer II).

which is a photochromic compound and can be used as a solid-phase photochromic material for optical recording of information on laser discs.

... 1608191 A1

0.43 g (2.5 mmol) of Fischer base and 0.73 g (2.5 mmol) of 1-phenyl-3-isopropyl-4-formyl5-selenolpyrazole are boiled in 5 ml of alcohol for 2 hours, 2 ml are distilled off alcohol and the reaction mixture is left overnight. The precipitate was filtered off and crystallized from toluene. Yield 0.85 g (76%), mp. 209210 ° C.

Found,%: C 66.7; H 5.9; N, 9.7; Se 17.2.

H 6.1;

C ₂₅ H ₂₇ N ₃ Se

Calculated,%: C 67.0;

N, 9.4; Se 17.6.

IR spectrum, cm ' ¹ . 1

1558 pl, 1540 pl, 1506 p 1477, 1460, 1433, 1408, 1340, 1292, 1277, 1233, 1113, 1088, 1027, 1006, 752, 737, '680.

UV spectrum (in propanol-2),>) _max , nm (g): 297 (7200), 422 (23000), 548 (15760).

, GMDS as., And, ppm (int; multiplicity): 1.43 (6H, d, I = 7.5 Hz, -CH (CH ₃ ) _g );

s,> C (CL ₃ ) _g ); 3.23 (1H,

NMR'N spectrum (SSC. Internal standard), activity,

1.76 (6H septet,

(ZN, s, N-qha Λ , 2 - 8, 13 (9H aroma.); 8.55 ' (1H, D, ¹ = 13.8 oL-CH =); 9.21 (1H, R, I = 13.8 6 ~ CH =). π p and m e P 2. Synthesis 1,3,3

'-trimethylindolin-2-spiro-2 ¹ - [2H ^ -selenopyrano [5, b-djpyrazole (I).

A polydisperse film of spiro selenopyran (I) is obtained by vacuum thermal sputtering at the VUP-4 installation of the merocyanine open-chain isodomer measure (II). Weighed portion of the compound is 2 mg, residual pressure 211 O'® torr, 'heater temperature 45 ° C. As a substrate, quartz plates with a size of 10 x 45 x 40 mm are used, placed at a height of 60 mm above the heater. Under these conditions, the spraying time is 30 s.

UV spectrum, ft _{M0) CS} , nm (D): 438 (0.66); 583 (0.05). .fifty

IR spectrum, ^, cm: 1593, 1562, 1506, 1497, 1476, 1460, 1433.1366,

133.7, 1324, 1288, 1273, 1230.1206,

1156, 1113, 1088, 1064, 1021,1006,

914, 836, 820, 750 686.

The obtained polydisperse film of spiroselenopyran (I) has a photosensitivity. Upon irradiation with light cft _{M <J (tc} 313 nm, reaction (I) -? (II) occurs in the irradiated areas, accompanied by staining, subsequent irradiation with visible light cft _{At0 (KC} = 576 nm causes its discoloration.

Compound (I) was obtained at other values of the residual pressure. Moreover, at P <1 · 10 ~ * torr, the yield of product (I) is 50-60%, at P ~ - 10 ^З Torr - 15-18%. The maximum residual pressure for the VUP-4 unit with an additional system of vacuum traps cooled by liquid nitrogen is P ~ 10 torr. Under these conditions, the yield of product (I) is 95%.

Compound (I) was obtained at various values of the temperature of the evaporator (at a constant residual pressure P = 2 -1 -1 ' ⁵ torr).

At T = 500 ° C, the film is optically inhomogeneous, at T = 450 ° the film is homogeneous, the deposition time is 30 s, at T = 400 ° C the film is homogeneous, the deposition time is 100-110 s.

Based on the data, the optimal solid-phase vacuum synthesis of compound (I) was chosen: residual pressure 1P <2 * 10 '^ torr, evaporator temperature T = 450 ° C.

Thus, a new method has been developed for the preparation of compound (I), which is a photochromic compound and, as a solid-phase photochromic material, allows multiple erasure and recording of optical information using radiation of various spectral composition.

Claims (4)

Claim The method of obtaining 1,3,3-trimethylindoline- 2-spiro-2 - ^ 2H ^ selenopyrano £ 5,6djpyrazole formulas by the fact that the thermal spraying is 1- £ (1,3, 3- trimethylindoliden-2) ethylidene ^ -1 phenyl-3-isopropyl-pyrazolin-2-ylidene- 4-s.eleon-5 in vacuum at 10 έΡέ 2 ^χ X10 ' ⁵ torr and a temperature of 400-450 ° C.