SU417425A1 - Method of preparing thionaphtheno-/2,3-c/-pyrylium perchlorates - Google Patents

Description

one

The invention relates to a process for the preparation of thionaphthio-2, 3-e1-pyryl perchlorates, which is of interest as outcomes of compounds for the synthesis of thione-2-thio-2, 3-c-pyridines, as well as potential physiologically active substances.

A known method for the preparation of thienosis, 4-c J-pyrylium salts, is accomplished in that 2,5-dialkyl-substituted 3-acetonylthiophene is acylated with carboxylic acid anhydride in

the presence of chloric acid with the ODIO-time heterocyclization of dicarbonyl compounds followed by isolation of the target product, but there is no information about the method of producing thionaphthen-2,3-e-perhlorate perchlorate.

According to the invention, the ketone of the thionaphthenic series, for example, 3-acetoylthionaphthene, is reacted with an excess of carboxylic anhydride in the presence of an equimolecular amount of 70% perchloric acid, followed by isolation of the target product in a known manner.

Example 1. To a solution of 1.9 g (0, oi mol) of 3-acetonylthionLtene in

10 ml (0.1 mol) of acetic anhydride is added dropwise 0.8 ml (0.01 mol) of 70% perchloric acid. After 30 mn of precipitated perchlorate crystal, 2,4-dimethylthionaphteno-2,3-c} pyril is filtered off, washed with 5 ml of acetic acid and 10 ml of ether, dried. 2.51 g (0%) of the product is obtained; m.p. 193.5-194, (yellow needles from

0 alcohol).

HI1%,% t C 49.63; H 3.81; C1 10.67; S 9.95.

H .. From 10.5.

3.5; Vy

 adseno,% 1 C 49.60; H C1 11.29; S 10.17.

five

IR spectrum 1620 (s), 1600, 1562,. 1543, 1447, 1100 (ots.), 625 (s) cif.

When treated with an alcoholic solution of akmnak, the quantity of the product is converted into 2,4-d methylthionaphthio-2, 3-c-nitride with so pl. 94-95 С (From hexaia).

Example 2. 2-Ethyl-4-methylthi-6-naphthene-2, 3-cJ-p-mly perchlorate is obtained via the use of propionic anhydride ACID. a: (stroke 71.61; mp. 199-200C (from alcohol).

Found,%: C 50.68; H 3.68; C1 10.62; 65

WITH, .

Calculated,%: VC 51.22; H

3.96; C1 10.74; S. .-

IR spectrum: 1618, 1100, 625 cm

Example 3. 2-Propyl-4-methylthionaphthene-2,3-e-pyrillium perchlorate is prepared using butyric anhydride. Yield 77.3%; m.p. 160-161.C (from alcohol).

Found,%: C 52.60; H 4.56; CJ 10.40; S 9.37. C, 5H, yC10yS.

. §Calculated,% i С H 4.38; C1 10.36; S 9.34.,

IR spectrum: 1618, 1100, 625 cm

Claims (1)

Claims. A process for preparing thio5 naphthyo-2,3-c-pyrily perchlorates, characterized in that the ketone of the tononaphthene series, for example 3-acetonylthionaphthene, is reacted with an excess of carboxylic anhydride in the presence of an equimolecular amount of 70% perchloric acid followed by isolation of the desired product in a known manner.