SU335937A1 - - Google Patents

Description

The invention relates to the preparation of perchlorinated cyclic aminovinyl ketones of the general formula

C1

C1

/ Rt

to.

where 1-M (СНз) 2; N (C2H5) 2; NC4H8O; NCsHio

 M (CH3) 2; N (C2H5) 2;

NC4H8O; NCsHio; Cl

The compounds obtained are not described in the literature, have a biological activity and can be used in medicine as pharmacological substances.

Methods are known for producing p-aminovinyl ketones by reacting p-chlorovinyl ketone RCOCn CHCl, where R is CH 3; C2H5, etc., with an aqueous solution of amine, p-aminovinyl ketones are used as anti-knock and intermediates for the synthesis of dyes and insecticides. However, methods for preparing cyclic perchlorinated aminovinyl ketones are not described in the literature.

by reacting a cyclic perchlorinated ketone containing a dichloromethylene group, for example 2,3-dichloro-5- (dichloromethylene) -cyclopentene - 2-dione-1,4, with aliphatic, cyclic or aromatic ammonia in an organic solvent medium, followed by isolating the target product with a known in a way. The resulting cyclic perchlorinated

aminovinyl ketones possess pharmacological activity and can be used in

NHCeHs; medicine as pharmaceuticals.

Example 1. 2,3-dichloro-5- (M, N-dimethyl) NHCeHs;

tylen) -cyclopenten-2-dione-1,4.

A solution of 2.46 g (0.01 g-mol) of 2,3-dichloro-5- (dichloromethylene) -cyclopentene-2-dione-1.4 in 100 ml of chloroform is placed in a round-bottom flask with a reflux condenser and a messenger.

With vigorous stirring, dimethylamine gas is passed into the solution for 10 minutes. The reaction mass is washed with 2 n. HC1, by water, is above Ca. After

chloroform distillation get 2.45 g (93% of

theory) of the product (where Ri R2 is CH (CH3) 2) in

as brilliant yellow crystals with m. pl.

215-217 C (from ethanol).

To a solution of 2.46 g (0.01 gmol) of 2,3-dichloro- (dichloromethylene) -cyclopente-11-2-dione-, 4 in 150 ml of ether, under energetic stirring and cooling, the ice and water are added during 45 missions by dropping 4 , 2 ml (0.04 g-mol) of diethylamine. The precipitated diethylamine hydrochloride is filtered off, and the reaction mass is treated as in Example 1. After distilling off the ether, 3.10 g of product are obtained (where Ri is R2 N (C2H5) 2 as yellow-orange crystals with mp 133-134.5 ° С ( from heptane. Yield 97.5%.

Example 3. 2,3-dichloro-5- (M, M-piperidipmethylene) -cyclopentene-2-dio-1,4.

To a solution of 2.46 g (0.01 gmol) 2,3-dichloro- (dichloromethylene) -cyclopenten-2-dione-1.4 in 100 ml of benzene while stirring and cooling for 45 minutes, 4.0 ml are added dropwise (0.04 M) piperidine. The reaction mass is treated according to example 2. After distilling off the benzene, 3.37 g of product (where Ri R2 NCsHio) is obtained in the form of bright yellow crystals with m.p. 191.5-193 ° C (from acetone). The yield is 98.4%.

Example 4. 2,3-dichloro-5- (H, M-morpholinochloromethylene) -cyclopenten-2-dione-1,4.

To a solution of 2.46 g (0.01 M) 2,3-dichloro-5- (dichloromethylene) -cyclopetene-2-dione — 1.4 V

100 ml of benzene was added dropwise with 2.0 ml (0.02 M) of morpholia. The reaction mass is treated according to example 2. After distillation, benzene is obtained. 2.78 g of the product (Ri, Rj - Cl) in the form of bright yellow crystals with m. Pl. 135-137 ° C (from methanol). Yield 94%.

Subject invention

The method of obtaining cyclic perchlorinated aminovinyl ketone of the general formula

H, / C1

where -Y (CH3) 2; NC4H80; NCsHio

2 -Y (CH3) 2; NC4H80; NCsHio; Cl characterized in that 2,3-dichloro-5 (dichloromethylene) -cyclopentene-2-dione-1,4 is reacted with amines in an organic solvent medium, followed by isolation of the target product by the lime method.