SU436058A1 - METHOD FOR PRODUCING DERIVATIVES 1 TIAZOLO - Google Patents

Description

one

FIELD OF THE INVENTION The invention relates to a method for the preparation of thiazolo (3,2-a) imidazolone-6 derivatives not described in the literature. These compounds can be used as biologically active substances, dyes or intermediates of their synthesis.

The literature describes a method for producing benzothiazolo (3,2-a) imidazolone-2 by reacting 2-aminobenzothiazole with bromoacetic acid, followed by cyclization of the intermediate 2-imino-3-carboxymethylbenzothiazoline by acetic acid and pyridine.

However, the reactions of this compound in the megylene group of the imidazolone core were not studied.

The proposed method for the preparation of thiazolo (3,2-a) imidazolone-6 derivatives of the general formula

 ABOUT

where Xi and Xa are hydrogen or Xi and X2 and the heterocycle bond between them forms a condensed benzene, tetrahydrobenzene or naphthalene nucleus; R is aryl or py- or six-membered heteryl is that the corresponding thiazoline derivative of the general formula

HrtX-CHvCOOR

S nh

x „

where X and X2 are as defined, and R is hydrogen or alkyl; or its hydrohalide salt is treated with an aldehyde when heated predominantly at boiling in an environment of an organic solvent, for example, in glacial acetic acid, in the presence of a base, for example acetate, followed by isolation of the target product by known methods.

The structure of the obtained compounds was confirmed by elementary analysis data and physicochemical methods of investigation (IR spectroscopy).

Example 1. Ilidea derivatives of thiazolo (3,2-a) imidazolone-6 (I, P table. 1).

To a solution of 1.58 g (0.01 mol) of 2-imino-Z-carboxymethylthiazoline in 5 ml of glacial acetic acid was added 0.82 g (0.01 mol) of anhydrous sodium acetate, 0.01 mol of aldehyde and 5 ml of acetic anhydride . The mixture is boiled for 30 minutes, cooled, poured into water, Oca34 ILIDENE DERIVATIVES TIAZOLO (3,2-a) IMIDAZOLONE-6)

436068

Table 1

the dock is filtered, washed with water and dried.

Example 2. Ilide derivatives benzothiazolo (3,2-a) imidazolone-2 (III, IV, table. 2).

To a solution of 2.36 g (0.01 mol) of 2-imino-Zkarbethoxymethylbenzothiazoline in 30 ml of LEILIDENE DERIVATIVES BENZOTHIAZOLO (3,2-a) IMIDAZOLONE-2a)

1.64 g (0.02 mol) of anhydrous sodium acetate and 0.01 mol are added to a solution of 2.36 g (0.01 mol) of 3-carboxymethyl-6-ethoxy-2-imiyiobenzothiazoline in 20 ml of glacial acetic acid. aldehyde. The mixture is boiling t 1 hour

ILIDENE DERIVATIVES 5, 6, 7, 8-TETRAHYDROBENZOTIAZOLE (3,2-a) IMIDAZOLONE-2)

To a solution of 2.76 g (0.01 mol) of 2-amino-3-carbethoxymethyl-4,5,6,7-tetrahydrobenzothiazoline hydrochloride in 15-20 ml of glacial acetic acid was added 1.64 g (0.02 mol ) anhydrous sodium acetate and 0.01 mol of aldehyde. The mixture was boiled for 1-1 hours 30 minutes and worked up as described in Example 1.

Example 5. Iliden derivatives of naphtho (1,2-d) thiazolo (3,2-a) imidazolone-2 (XI-HP1, Table 4).

To a solution of 1.36 g (0.05 mol) of 2-imino-Zcarbmethoxymethylnaphtho (1,2-d) thiazoline in 20 ml of glacial acetic acid is added

For acetic acid, 1.64 g (0.02 mol) of anhydrous sodium acetate and 0.01 mol of aldehyde are added. The mixture was boiled for 2 hours and worked up as described in Example 1.

Example 3. Ilide derivatives 7ethoxybenzothiazolo (3,2-a) imidazolone-2 (V, VI, Table. 2).

Table

30 min and treated as described in example 1.

Example 4. Iliden derivatives 5,6, 7,8 - tetrahydrobenzothiazolo (3,2-a) imidazolone-2 (VII-X, Table 3).

Table

0.82 g (0.01 mol) of anhydrous sodium acetate and 0.005 mol of aldehyde.

The mixture was boiled for 1 hour and worked up as described in Example 1.

Example 6. 3-Carbethoxymethyl-4,5,6,7-tetrahydro-2-iminobenzothiazole hydrochloride.

To a solution of 15.4 g (0.1 mol) of 2-amino-4,5,6,7 tetrahydrobenzothiazole in 30 ml of ethanol was added 12.2 g (0.1 mol) of ethyl chloroacetic acid ester. The mixture was boiled for 16 hours, the solvent was distilled off in vacuo to dryness, a mixture of 20 ml of acetate and 50 ml of ether was added to the residue, and the precipitate was filtered off. NAIDO (1,2-a) TIAZOLO (3,2-a) IMIDAZOLONA-21 ELECTRONIC DERIVATIVES Notes to tables 1-

stroke 18.1 g (69%), so pl. 208-209 ° С (from acetone-water mixture, 50: 1).

Found,%: C 47.4; H 5.9; C1 12.9; N 9.9; S 11.8.

CiiHi6N202S-HCl.

Calculated,%: C 47.7; H 6.2; C1 12.8; N 10.1; S 11.6.

Example 7. 2-Imino-3-carbomethoxymethylnaphtho (1,2-d) thiazoline.

To a solution of 4 g (0.02 mol) of 2-amino naphtho (1,2- (1) thiazole in 20 ml of methanol was added 3.1 g (0.02 mol) of methyl bromoacetic acid). The mixture was boiled for 15 hours, cooled, poured into water, neutralized with an aqueous solution of sodium bicarbonate, the precipitate is filtered off, washed with water and dried (yield: 5.1 g (94%), mp 162-163 ° C (from ethanol).

Found,%: C 61.4; H 4.3; N 10.2; S 12,0.

CuHiaNaOsS.

Calculated,%: C 61.7; H 4.4; N 10.3; S 11.8.

Subject invention

Claims (2)

1. A process for the preparation of thiazolo (3,2-a) imidazolone-6 derivatives of the general formula CHR That blitz 4 where Xi and X2 are hydrogen or Xi and X2 and the heterocycle bond between them forms a condensed benzene, tetrahydrobenzene or naphthalene core; R is an aryl of a pythiol or a heterocycle of heteryl, characterized in that the corresponding thiazoline derivative of the general formula Xf- i -CH -COOR v- XgSNH where Xj and X2 have the indicated values, a R is hydrogen or alkyl, or its halohydrate, is reacted with an aldehyde when heated in an organic solvent, for example in glacial acetic acid, in the presence of a base, followed by isolation of the target product by known techniques. 2. The method of claim 1, wherein the process is carried out at the boiling point of the reaction mass. 4:) For analysis, the substances were purified by crystallization from dimethylformamide (I-VI, VIII, IX, XI, XIII) or a mixture of ethanol and dimethylformamide 1: 1 (VII, X, XII). b) QiHjNOa-residue of 5-nitrofurfural.