SU394373A1 - METHOD OF OBTAINING BEIZO-1b] -a-KARBOL INOV - Google Patents

Description

The invention relates to the field of production of new biased benzo-b-c-carbolines (quinindolines), which can be used in the pharmaceutical industry.

A known method for the preparation of hingle.1n1P1P or its substituted; condensation of aromatic o-nitroaldegnds with oxindo halsch, with the following recovered, is obtained by the foot of intermediate product and far) in the cyclization.

Proposed Snack

bepz-b-a-carbolines consists in condensation; 2-chloroindole-3-aldehyde with aromatic amipamn when heated, preferably up to 150-190 ° C.

The proposed snozob is simpler in comparison with the known one, besides allowing, along with the well-known United States, to obtain new substituted hnnindoliums, namely, those substituted in the hypoline ring, which are obtained in a known way by the conglomeration.

The structure of the compounds obtained is confirmed by elemental analysis,

UV spectra and comparison with the samples of the known constitution. Quinindoles have a lung fluorescence.

Example 1. Benzo-L-a-carboline (quinindoline). A mixture of 1 g (5.5 mmol) of 2-chloroindole-3-aldehyde and 1.5 g (16.5 mmol) of aniline was boiled for 2 hours. After crystallization, the crystallized after the cooled mass is unmixed for a few minutes with 5-6. Or 5-10% alcohol solution of potassium hydroxide, the precipitate is sucked off and washed with a coolant. Yield 1.1 g (91%). After recrystallization from the feast ii din aa.tgo-pearl.mutrovye plate with so pl. 338-340 ° C. UV spectrum (in methanol): /.,, 223, 269, 317, 331, 370 N. n (Ige 4.62; 4.84; 4.25; 4.38; 3.63). Literary data; m.p. 340-342 °, UV-spectrum (in alcohol): AMIKC 272, 319, 334, 372 nm (Igs 4.73; 4.13; 4.28; 3.57).

Acetyl derivative, so pl. 185-186 ° C (from methanol). Literary data: so pl. .

Similarly, 0.36 g (92%) is obtained from 0.3 g (1.66 mmol) 2-chloroindole-3-aldehyde and 0.27 g (2.5 mmol); g-toluidine (0.5 hour at 180 °) 2 -metnbenzo-b-a-carboline, so pl. 303-305 С (from П1фиднна).

Found,%: C 82.2, 82.4; H 5.1, 5.1.

C, 6H, 2N2.

Calculated,%: C 82.7, H 5.2. UV spectrum (in methanol): Lmcbc 225, 271, 318. 333, 372 nm (Igs 4.68; 4.92; 4.34; 4.48; 3.71).

Acetric derivative, so nl. 169-171 ° C. Found,%: C 78.9, 78.9; H 5.0, 5.1. Example 2. 4-metilbe1 30-b-a-carbol-1P (-1-m hundred l quinine and idol). A mixture of 0.4 g (2.3 mmol) of 2-chlornndol-3-aldehyde and 0.4 g (3.7 mmol) of o-tolundine is heated for 1 hour at a temperature of 190 ° C. Oto- is: rubbed with li mixed with 2- -3 ml of 5-10% alcohol solution of potassium hydroxide. The precipitate is filtered off and washed with alcohol. After purification on a column with aluminum oxide (degree II activity) in a 25: 1 toluene-ethyl acetate system and recrystallization from benzene, pure 4-methylchioindoline with a m.p. 218-219 ° C, yield 0.2 g (40%) -. %: C 82.1, 82.7; G1 5, HaibiOiK), C.sHisNa. Calculated,%: C 82.7, P 5.2. 272, UV spectrum (in methanol): i.p., px223, 317, 331, 370 nm (IgF, 4.65; 4.99; 4.27; 4.44; 3.69). Acetyl derivative, so pl. 175-1 (from methanol). The best,%: C 79.0, 79.2; And 5.0, 5.1. C | 8H; 4N20. Calculated,%; C, 78.8; P 5.1. Also gz 0.3 g (1.66 mmol) of 2-chloropndol-3-aldehyde and 0.3 g (2.4 mmol) of o-anisidine (elution with a mixture of tolz-ol-ethyl acetate 2; 1) are given in 4- methoxypsyndol with t. PL. 270-272 ° C (from benzene with toluene), pykhod 0.12 g (30%). Acetyl proizvodimoe, so pl. 220-22GS (from methanol). Found,%; C 74.3, P 5.5. Ci8n; 4N202. Calculated,%; C, 74.5; H 5.0. A method of producing beiso-b-a-carbolines, characterized in that the 2-chloroindole-3-aldehyde is reacted with primary aromatic amines when heated followed by a selection of the target product known techniques. 2. A method according to claim 1, characterized in that the process is conducted at a temperature of 150-190 ° C.