PL198985B1 - New derivatives of 1,2,4-triazole and method of their production - Google Patents

Abstract

. New 1,2,4-triazole derivatives of the general formula 1 shown in the drawing, where R1 is a phenyl, 2-pyridyl, 4-pyridyl group and R2 is a phenyl, 4-tolyl group. 2. A method for obtaining new 1,2,4-triazole derivatives of general formula 1 shown in the drawing, where R1 is a phenyl, 2-pyridyl, 4-pyridyl group and R2 is a phenyl, 4-tolyl group, characterized in that N3-substituted amidrazones of general formula 2, where R1 and R2 have the meaning given above, are subjected to a cyclocondensation reaction with maleic acid anhydride of formula 3, wherein the reaction is carried out in a non-polar solvent, preferably ether, for about 48 hours, then the separated precipitate is filtered off and purified by crystallization from alcohols, preferably methanol.

Description

Description of the invention

The subject of the invention are new 1,2,4-triazole derivatives of the general formula 1 shown in the figure, in which R ¹ represents: phenyl, 2-pyridyl, 4-pyridyl groups and R ² : phenyl, 4-tolyl groups and the method of their preparation .

1,2,4-triazole derivatives are mainly obtained from thiosemicarbazide or its alkyl or acyl derivatives (Freund M .: Chem. Ber. 29, 2483 1894) from s-triazine (Gtrundmann Ch., Ratz R .: J. Org. Chem. 21, 1037 1956) and amidrazones (Bany T .: Chem. 42, 247 1968, Modzelewska-Banachiewicz B., Matosiuk D .: Pharmazie 54, 588 1999, Modzelewska-Banachiewicz B., Kamińska T .: Eur. J. Med. Chem. 36, 93 2001). 1,2,4-triazole derivatives are also included in many compounds with various pharmacological effects, e.g. stimulants - Hexazoles, hypnotics - Fepitriazole, antifungal - Azaconazole (Negwer M ;: Organic-chemical drugs and synonyms, 6th edition 1987) .

The new 1,2,4-triazole derivatives of the general formula I, in which R ¹ and R ² represent the above-mentioned groups, show anti-inflammatory, antifungal, antibacterial and antiviral activity.

The method of obtaining new 1,2,4-triazole derivatives of the general formula 1 shown in the figure, in which R ¹ is a phenyl, 2-pyridyl, 4-pyridyl ^{group and R 2 is} a phenyl, 4-tolyl group, consists in the following: ^{The 3-} substituted amidrazones of the general formula II, in which R ¹ and R ² are as defined above, are cyclocondensed with maleic anhydride of the formula III, the reaction being carried out in a non-polar solvent, preferably with ether, for about 48 hours. The separated precipitate is filtered off and purified by crystallization from alcohols, preferably methanol.

The obtained compounds are solid crystalline substances soluble in water and polar solvents (alcohols, dimethylacetamide and dimethylsulfoxide), and insoluble in non-polar solvents such as ether, alkanes.

P r z k ł a d 1.

2.15 g (0.01 mol) of N ^{3-phenyl-2-pikolinamidrazonu} and 0.98 g (0.01 mole) of maleic anhydride suspended in 25 cm ^{3 of} anhydrous diethyl ether and allowed to stand for 48 hours at room temperature. After this time, the resulting precipitate was filtered off, washed with anhydrous ether and purified by crystallization from methanol. 2.0 g (68% yield) of 3- [3- (2-pyridyl) phenyl-1,2,4-triazol-5-yl] acrylic acid having a melting point of 224 ° C were obtained.

Elemental analysis for the Formula C16H12O2N4 (MW 292.16)

% C = 65.75% H = 4.10% N = 19.17 was calculated

% C = 65.40% H = 3.99% N = 19.30 was obtained

IR spectrum KBr (cm ^-1 )

3061 arom, 2481, 920 OH, 1700 CO, 1206 C-O, 1000 vinyl.

¹ H NMR spectrum (ppm, DMSO, TMS)

6.33 (d, 1H, CH), 6.46 (d, 1H, CH-CO), 7.36-8.37 (m, 9H, arom), 13.62 (s, 1H, COOH)

P r z k ł a d 2.

2.19 g (0.01 mol) of N ³ -4-tolyl-2-picolinamidrazone were reacted with 0.98 g (0.01 mol) of maleic anhydride as described in point 1. After crystallization from methanol, 2 g of ( 65% yield) of 3- [3- (2-pyridyl) -4- (4-tolyl) -1,2,4-triazol-5-yl] acrylic acid, m.p. 178 ° C.

Elemental analysis for the Formula C17H14O2N4 (MW 306.17)

% C = 66.66% H = 4.57% N = 18.30 was calculated

% C = 66.19% H = 4.39% N = 18.06 was found

IR spectrum KBr (cm ^-1 )

3051 arom, 2970 alif., 2439, 944 OH, 1708 C = O, 1203 C-O, 1000 vinyl.

¹ H NMR spectrum (ppm, DMSO, TMS)

2.36 (d 1H, CH3), 6.36 (d 1H, = CH), 6.46 (d 1H, = CHCO), 7.20-8.38 (m 8H, arom) , 13.62 (s. 1H, COOH)

Claims (2)

1. New 1,2,4-triazole derivatives of the general formula 1 shown in the figure, wherein R ¹ is phenyl, 2-pyridyl, 4-pyridyl and R ² is phenyl, 4-tolyl. 2. The method of obtaining new 1,2,4-triazole derivatives of the general formula 1 shown in the figure, in which R ¹ represents a phenyl, 2-pyridyl, 4-pyridyl ^{group and R 2 is} a phenyl, 4-tolyl group, characterized in that N ³ -substituted amidrazones of general formula II, in which R ¹ and R ² are as defined above, are cyclocondensed with maleic anhydride of formula 3, the reaction being carried out in a non-polar solvent, preferably with ether, for about 48 hours, then the separated precipitate is filtered off and purified by crystallization from alcohols, preferably methanol.