SU583755A3 - Method of preparing heterogeneous ring compounds or salts thereof - Google Patents

Description

(54) AALSOB FOR GETTING HETEROCYCLIC COMPOUNDS

OR THEIR SALTS The target products are isolated as o, but they are transferred or copulated. The process is carried out predominantly in an organic solvent inert at the time of the reaction, for example, in such cyclic ether or open-chain ether, like dioxane or dimethyl ether diethyping) 1I cop. In appropriate cases, as a solvent, a solvent is used in an excess of a compound of the general formula III. The reaction can also be carried out in a melt. Compounds of general formula I can be isolated from the reaction mixture and procedure. The starting compounds of general formula IJ are known or can be obtained by known methods, starting from the corresponding oxyindole or oxyfluorene-9-oct. Compounds of general formula HI are known. Example I, 4-G2-Oxy-3 -. {2 | 2.5 / 5 "Tbtramethyl-1-pyrrolidinyl) -propoxy - 4 h (2.3-9-proxy-propoxy) -9-. fluorene1 is heated from 4 g of 2,2,585-tetramethyapyrrolidine in 30 ml of donoxane in an autoclave for 15 hours to 1SO ° C. After cooling, the reaction mixture is evaporated and the residue is taken up in ether and extracted with 2N hydrochloric acid. The aqueous solution is brought to alkaline and exhaustively extracted with methylene chloride. The methylenechiporide phase is depressed and the residue is cristapized from a mixture of ethyl acetate acetic acid and petroleum ether. The melting point of the chain product is 137-138 ° C. Example 2.. (L Aairidinyl) -X-9-fpioponon. 4 g of 4- (2,3-epoxypropoxy) -9-fpuorenone is incubated overnight with 15 ml of ethylenimyl at room temperature. Excess etipenimine is then distilled off, the residue is extracted with ether and the solution is evaporated until crystallization begins. The flame temperature of the target product is 113-116 C, Example 3, 4-G2-Oxy-3- {, 2-dihydro-2-imino-1-pyrimidinyl) -propoxy5-9 | -fluorenone. 5 g of 4- (2,3-epoxypropoxy) -9-fluorenone and 3, 8 g of 2-aminopyrimidine are heated for 30 minutes to 10 ° C, the melt is dissolved in ethyl acetate and extracted with 2N hydrochloric acid. The hydrochloride precipitated out as a gum is made alkaline and extracted with methylene chloride. Then the solvent is evaporated and the residue is crystallized from ethanol (m.p., 178-179 ° C). Similarly, the outcome of the starting compounds of formula II, where X and Y together mean -O- or X-hydroxy group and Y-chloro, and the general formula U, give compounds of general formula I listed in the table.

9 Fluorenone4

Thats kie4

eleven

WITH

™ -2

".

2-Indolinon4

Same4

9-fluorenone4

2 2

Same4

four

, 2,6 „6-Tetrametipiperidino

8-Norpropanil

2,2,5,5-Tetramethyl-1 -pyrrolidinyl

2.2, b5v-tetramethyl

piperidine

2,2,5,5-Tetramethyl-1pyrrolidinyl

9-Azabicycpo2,3,1 non 9-yl.

1-Pyrrolidinip

2,6-dimethylphericin

9-Azabicyclo 3,3, 9-yl

9 - Fpuorenon 4

13

Also

14

15

12-Indopinon4

16 21

3Top4 m. hydrochloride. Example 22. 4-C2-Hydroxy-3- (2, 2,5,5-tetrametip-1-pyrrolidinip) -propoxy 3 -fpuorenone. This compound is obtained anapogically as Example I, but instead of 4- (2,3-epoxy-propoxy) 9-fluoro- onon, 4- (3-bromo-2-hydroxypropoxy) -9-fpuorenone is used. The melting point of the desired product is 137-139 0, Example 23, 4- 2-Hydroxy-3- (2,2, 5,5-tetra letyl-1-pyrrolipinyl) -propoxy 9-fgEy oronone. This compound is prepared according to Example G, the outcome (2-hydroxy-3-tosyloxypropoxy) -fluorene-9-one instead of 4- {2,3-epoxypropoxy) -9-fpuorenone. The melting point of the obtained compound is 137-139 ° C.: Example 24. 4- 2-Hydroxy-3- {2,2, 6,6-tetrametypiperidino) -propoxy -2-indolinone. Analogously to example I, starting from 4- (2-hydroxy-3-tosyloxypropoxy) -2-indolinone instead of 4- (2,3-epoxypropoxy) -9-fluorenone, is obtained using the corresponding amine of the general form nfci III above compound, so pl. its 177-178 ° C. Example 25. 4- 2-Hydroxy-3- (2,2, 6,6-tetramethylpiperidino) -propoxy -2-indolinoH. Analogously to Example I, starting from 4 (2-hydroxy-3-mezipoxypropoxy) -2-indopinone instead of 4 (2 3-epoxypropoxy) -9-fluorenone, is obtained using the corresponding amine total form) above; the specified connection, so the PP. its 177-178 0.

Groponzheii tabpitsy

1,2-L gilro-2-imino-.1-feast IDN

2,2,5,5-Tetrametnp-1-pyrropidinyl

Azabicyclols, 3, l HOIS2-en-9 - il

Also

1.2 Digitsro-2-imino-1-pyridine formula of the invention. Method of obtaining heterocyclic formulations of the general formula} HE Het-O-CHj-CH, Het - residue 2 of indolinone, which is with a side chain in the 4 t position of a new ring, or residue E fluorene zannyy with a side chain in position 1, 2 or 4 fuporenon ring; R, is a radical: / PI x DSNgU -O 1 LG7-d 2V c. Rj is hydrogen or methyl; A - B - ethylene or vinide; n 2 or 3; p 1 or 2, whether their salts, of which it is soepeniepé common jT Het - O —CH., - SI X Y I Het has a directive: 1e BFjUiie value; hydroxy group; Y - halogen or group. - O-, hae Kd - phenyl, weight of lower alkyl, silt X and Y together designate -0-, are subjected to interaction at a temperature from room temperature to 2OO ° С with the compound of the general formula III RH, where R has the indicated sign, with (by extracting the target product in the form of ossaaan or in salt). Priority to signs: 19.OVL4 at Het is the remainder of 9-f oorov, which is associated with the boxed chain in the position of 1,2 or 4 ({ is a radical; A "g% where RJ is hydrogenated or methyl; L is B etipei or Binnpen; 2 or 3; n" 1 or 2. 06/19/74 with Het is the residue of 2-indolinone, which is n with a side chain in position 4 of the inaolin ring; lit is the radical - / L –t Rf And where HI is hydrogen or methyl; AB — ethylene n in 2 or 3; 1 IRN 2. Sources of information taken into account Expertise: 1. Weigand-Hilgetag Experimental Methods b Organic Chemistry, M., Himi, 1988, pp. 415.