SU496276A1 - The method of obtaining condensed-substituted quinolones - Google Patents

Description

 3

The structure of the target compounds has been unambiguously proven using PMR and mass spectra.

Example 1. 1-Methyl-4-oxo-9-benzyl-1H, 2,3,4,9-tetrahydropyrrolo (2,3-b) quinoline hydrochloride.

To 4.0 g (0, O2 mol) of 1-methyl-4-oxo-1H, 2,3,4,9-tetrahydropyrrolo {2,3-b) quinoline in 40 ml of dry dimethylformamide is added at 70 ° C over 1 hour, 0.92 g (O, O4 mol) of sodium hydride, kept for 4 hours at 9 ° C, then 3.15 g (O, O 2 mol) of benzyl chloride was added in 5O minutes and the reaction mixture was held at 100 seconds for 3 hours. The reaction mass is evaporated, chloroform is added to the residue, the solution is filtered, the filtrate is washed with water. The chloroform layer was dried with sodium sulfate, filtered, and chloroform was evaporated. The residue is dissolved in acetone, alcohol rastor HC1 is added, and the precipitate is filtered. Compound weight 3.7 g (55%), t, pl. 19 ° -1 ° C (from alcohol).

Found,%: C 68.5; H 5.84; N 8.41; C1 10.63.

19 l8 2 - 2 Calculated,%: C 67.9 O; H 5.98;

KZ, 37; c: C1 10.58. Example 2. Hydrochloride of 1-methi-5-oxo-1O-benzyl-1,2,3,4,5,10-hexahydropyrido (2,3-b) quinoline.

It is prepared analogously to example 1 by reacting 1-methi-5-oxo-1,2,3,4,5, 10-hexahydropyrido - (2,3-b) quinoline with benzyl chloride; a base was synthesized from which; In dry ether by adding an alcoholic solution of HC1-. radiate hydrochloride, yield 85%, so pl. 172-3 ° C (from alcohol). Found,%: C 69.26; H 6.45;

N 7.95; C1 10.17. N o-HCl-O.

Calculated,%: C 68.57; H 6.29; N 8.02; C1 10.15.

Example 3. Hydrochloride of 1-methyl-6-oxo-benzyl-1H, 2,3,4,5,6,11-goxagidroazepino (2,3-b) quinoline.

Prepared analogously to example 1 by reacting 1-methyl-5-oxo-1H, 2,3,4,5, 6,11-hexahydroazepino (2,3-b) quinoline with benzyl chloride, a base was synthesized, from which, in acetone, an alcohol solution of HC1 was obtained by adding hydrochloride, yield 60%, so pl. 152-3 C (from isopropane).

Found,%: C 70.74; H 6.57; .N 8.02; C1 9.78.

C .. O-NA.

Calculated,%: C 71.09. H 6.49;

N 7.89; C1 1O, O2. . Example 4. Hydrochloride; -methyl-4-oxo-9- (V, M-dimethylamino / nropyl 1H, 2,3,4,9-tetrahydropyrrolo (2,3-b) quinoline.

Prepared analogously to example 1 by reacting 1-methyl-4-oxo-1H, 2,3,4,9-tetrahydropyrrolo (2,3-b) quinoline with - (N, N-dimethylamino nropyl chloride, the base was synthesized, from which in acetone the addition of alcohol hydrochloride solution of HC1 was obtained, yield 58%, mp 236- .7 ° C (from alcohol). Found: C 54.2 O; H 7, O7;

N 10.74; C1 18.77.

. Calculated,%: C 54.25; H 7.18; N 10.17; C1 18.78.

Example 5. 1-Methyl-5-oxo-10 hydrochloride (V-yKliN-dimethylamino / prog saw) -1,2,3,4,5,1O-hexahydropyrido (2,3-b) quinoline.

Prepared analogously to Example 1 by reacting 1-methi-l-5-oxo-1,2,3,4,5, U-hexahydropyrido (2,3-b) quinoline with - (NI N -dimethylamino propyl chloride

a base was synthesized, from which hydrochloride was obtained in dry ether of an alcohol solution of HC1, yield 56%, so pl. 187-8 C (from iso-propanol). ,,

Found,%: N 11.16; C1 16.08

C.j gH2gN30-2HCl -,. 0,5H20:

Calculated,%; N 11.23; C1 18.63. Example 6. 1-Methyl-6-OXO-11- (V- / N | N-dimethylamino / propyl) hydrochloride -1 H, 2,3,4,5,6,11-hexahydroazepino (2,3- c) quinoline.

Prepared analogously to example 1, 1-methyl-5-oxo-1H, 2,3,4,5,6, 11-hexahydroazepino (2,3-b) quinoline was reacted with V (NI M -dimethylamino) propylchporide to synthesize a base. the hydrochloride obtained from the ear in the hearing ether by the addition of an alcoholic solution of HC1, yield 87%, so pl. 187-8 C (from iso-propanol).

Found%: C1 16.21:

  z ° - - 3 7 ° Calculated,%: C1 16,19. Example 7. Hydrochloride 1-mrtil6-oxo-11- (B - / H -dimethylamino / / ethyl) -1H, 2,3,4,5,6,11-g-rxahydroazrpnno (2,3-b) quinoline.

Get similar to ifpHK-reiiy .1. in .. (h-action of 1-st. II, 2,3,1, .5P, I, 11-hexahydroazepino (2,3-B) quinoline: A (NM-dimetypamyu} ethylchporid synthesized base, from the hydrochloride obtained in acetone with the addition of alcohol solution HC1, yield 60%, mp 174- .. 6 ° С (from iso-propanol), Found,%; C 54.58; H 7.45; N 10.75. C1 17.55., 3.2HCia, 5H20. Calculated,%: C 54.14; H 7.52; N 10.53; C1 17.79; Example b. Hydrochloride 1 — MetS1 Oxox-11 (/ / 4-benzoylpiperisino / propyl) -1H, 2,3,4,5,6,11-hexahydroazepino (2,) quinoline. Prepared analogously to example 1 using 1 methyl - 6 - oxo-1H, 2,3,4 , 5,6,1 -hexahydroazepino (2,3-b) quinoline with - / 4-be zoylpiperazino / propyl chloride synthesized a base from which in dry ether with the addition of an alcoholic solution; solution of HC1 hydrochloride, output 35% j, m.p. 163,, - (from i-prop: “nol) .. --- ..- , „-, ... Found,%: C 60.93; H 6.92;: N 10.86; C1 12.491. Calculated, with 61.20; H 6.92; 10.20; C1 12, 93.: PRI MER 9. 1-methyl hydrochloride,: -6-QKco-ll {i -3,4-, 5 - trnmethoxyben; Zoylox and (propyl) -1H, 2,3,4,5,6,11-hexa: hydroazepino (2,3-b) quinoline. Analogously to Example 1, it is prepared by the action of 1 methyl-6-oxo-1H, 2,3,4,5,6, -hexahydroazepino (2,3-b) quinoline C. , 4, 6 trimethoxybenzoyloxy / propyl chloride synthesized a base, from 1 of which hydrochloride was obtained in dry ether by adding an alcoholic solution of HCl, chloride, yield .45%, mp, 156 - .. 7 ° С (from isopropanol) . ; Found.;%: C 62.47; H 6.30; N 5.53, C1 6.61. 7 32 2 ° 6НЬ Calculated,%: C 62.73; H 6.39; 5.42; C1 6.87. Example 10 Hydrochloride 1-methyl-6-oxo 11/4-nitrobenzyl / -1H, 2,3, 5,6,11 hexahydroazepino (2,3-b) quinline. Prepared analogously to example 1 by the action of 1-methyl 6-oxr-1H, 2,3,4,5,6,; 11-hexahydroazepino (2,3-b) quinoline A with p-nitrobenzyl bromide synthesized a base, from which in benzene, adding an alcoholic solution of HC1, contains half, pl, 164,5an hydrochloride from alcohol). Found,%: C 62.91; H 5.51; N 10.44; C1 8.81. 3 Calculated,%; C, 63.08; H 5.51; N 10.51; C1 8.87. , Example 11, Hydrochloride 1 meth nl 6 - oxo-11-methyl 1H, 2,3,4,5,6,11 hexahydroazepine (2,) quinoline. but. Prepared analogously to example 1 using the reaction of 1-methyl 6-oxo-1H, 2, 3,4,5,6,11-hexahydroazepino (2,3-b) inoline with methyl iodide, synthesized base, from which I added alcohol solution HC1 oluchen guide {cooled, yield 51%, so pl. 55- 6. ° C (from iso-propanol}, mass. + Spectrum: M 242. Found,%: N 9.77; C1 12.07, 15 P8- 2 - Calculated,%: N 1O, O5 ;. C1 12.75. B. Using an equimolar amount of sodium ethoxide, the compound described in Example A is obtained, yield 20%. Subject of the Invention A method for producing fused M-substituted quinolines of the general formula: where D is alkyl, aralkyl, 1O-dialkylaminoalkyl and 3, 4,5-trimethoxybenzoyloxyapkil; ft is an integer, with a value of 1-3, 0 tl and h and y and the fact that it is a compound of the general formula where fx - has the indicated value; m of general formula R - X, where - has the indicated meaning, and X is a halogen, for example, chlorine, broth, aghi iodine in an organic solvent, mainly in dimethylformamide, in the presence of sodium hydride or an alkali metal alcoholate, followed by isolation of the desired product in the free in the form or in the form of: an acid additive salt.