Chinese Chemical Letters  2014, Vol.25 Issue (04):553-556   PDF    
Microwave assisted one-pot tandem three-component synthesis of 2,4,5-triary1-2-4-dihydro-3H-1,2,4-triazol-3-one derivatives
Bagher Mohammadia , Mehdi Adibb    
Corresponding authors at:a Department of Chemistry, Payame Noor University, Tehran 19395-3697, Iran;
b School of Chemistry, University College of Science, University of Tehran, Tehran 14155-6455, Iran
Abstract: This work described a one-pot tandem three-component synthesis of 2,4,5-triaryl-2,4-dihydro-3H-1,2,4-triazol-3-ones using a simple reaction between phenylhydrazines, benzaldehydes and phenyl isocyanates under microwave irradiation and solvent-free conditions in good to excellent yields.
Key words: Tandem multicomponent reactions     Solvent free     Heterocycle     Microwave     Triazole    
1. Introduction

Multicomponent reaction (MCR) is a chemical reaction where three or more compounds react to form a single product. By definition,MCRs are those reactions whereby more than two reactants combine in a sequential manner to give highly selective products that retain the majority of the atoms of the starting material. In the past decade,multicomponent reactions involving the condensation of three or more reactants either in tandem or in singlestephavebecomeanintegralpartofdrugdiscovery[1, 2, 3, 4, 5, 6, 7, 8, 9].The 1,2,4-triazol-3-one (1,2,4-triazolone) ring structure is found in a number of biologically active compounds. Some 1,2,4-triazolones havebeenshowntobeangiotensinIIantagonists[10],antimicrobial, antitumor agents [11, 12, 13] and anticonvulsants [14]. Several drugs possessing triazolenucleushavebeenapprovedformarketing,such as alprazolam (anxiolytic agent,tranquilizer),vorozole (antineo- plastics,nonsteroidal competitive aromatase inhibitors),etoper- idone (antidepressant),TAK-187 and Syn-2869 (antifungal agents) [15],nefazodone (antidepressant,5-HT2 A-antagonist),rizatriptan (antimigraine agent),trapidil(hypotensive),trazodone (antidepres- sant,anxiolytic,selectively inhibits central serotonin uptake) and triazolam (sedative and hypnotic) (Fig. 1) [16].

Fig. 1. Examples of biologically active 1,2,4-triazolones: (a and c) agricultural fungicides,(b) TAK-187 (antifungal),and (d) AT1-receptor antagonist.

There are many methods reported for the synthesis of the 1,2,4- triazolone ring [17, 18, 19, 20, 21]. The most common synthetic methods involve a cyclization-dehydration sequence of acyl semicarba- zidesinalkalinesolutions[22],reactionbetween 1,2,4-triazolium salts with aqueous potassium carbonate [23],the condensation of mono Boc-protected hydrazines with acyl isocyanates and the subsequent deprotection and then an intramolecular cyclization of the intermediate [24],a reaction of amidrazones and isocyanateestersandthecyclizationoftheimidoylsemicarbazide of ethyl chloroformate and N-1-tosylamidrazones [25],the cyclization of 1-aryl-1 nitroso-3-(2-pyridylmethyl) ureas [26] and a reaction between thiocarbohydrazide and substituted benzoyl hydrazine [27].

High-speed synthesis promoted by microwaves irradiation has attracted a considerable amount of attention in recent years. Using a microwave oven in microwave-assisted organic synthesis (MAOS),not only reduces chemical reaction time from hours to minutes,but also reduces side reactions,increases the yields,and improvesreproducibility.Therefore,manyacademicandindustrial research groups are already using MAOS as a forefront technology for rapid optimization of reactions,for the efficient synthesis of new chemical entities,and for discovering and probing new chemical reactivity [28, 29].

Asapartofoureffortsonthedevelopmentofsimplemethodsto prepare biologically active organic compounds [30],I used one such simple method for the synthesis of the scaffold (1,2,4- triazole-3-ones). I wish to report the synthesis of a trisubstituted 1,2,4-triazole-3-one derivatives 4 by a tandem three-component condensation of phenylhydrazines 1,benzaldehydes 2 and phenyl isocyanates 3 (Scheme 1).

Scheme 1. One pot synthesis of 2,4,5-triary1-2-4-dihydro -3H-1,2,4-triazol-3-ones.
2. Experimental

All starting materials and solvents were obtained from Merck (Germany) or Fluka (Switzerland) and were used without further purification. The methods used to monitor the reactions were TLC and NMR. Melting points were measured on an Electrothermal 9100 apparatus and were uncorrected. IR spectra were measured on a Jasco 6300 FTIR spectrometer.1H NMR and13C NMR spectra (CDCl3) were recorded on a BRUKER DRX-300 AVANCE spectrom- eter at 300 MHz and 75.5 MHz,respectively. Elemental analyses were performed using a Heraeus CHN-O-Rapid analyzer. Mass spectra were recorded on a FINNIGAN-MATT 8430 mass spec- trometer operating at an ionization potential of 70 eV. Preparative layer chromatography (PLC) plates were prepared from Merck silica gel (F254) powder.

Generalprocedureforthepreparationof4a-k:Thisreactionwas carried out using two protocols,namely microwave and conven- tional heating methods. Both methods were carried out by first mixing the arylhydrazine 1 and the arylaldehyde 2 at room temperature. After a fewminutes and nearly a complete conversion to the corresponding arylhydrazone5 was achieved,asindicated by TLC monitoring,the isocyanate3 was addedto the reaction mixture andinthefirstmethod,themixturewasirradiatedundermicrowave irradiation and in the second method the reaction mixture was heatedandstirredonamagneticstirrer.Theworkupprocessofthese methods is the same.1H NMR analysis of the reaction mixtures clearly indicated the formation of 1,2,4-triazol-3-ones 4. The structures of the isolated products were assigned on the basis of IR,1H NMR and13C NMR spectroscopy,mass spectrometry and elemental analysis. The mass spectrum of 4a displayed the molecular ion (M+) peak at m/z 375,which was consistent with a 1:1:1 adduct of phenylhydrazine,3-methyl benzaldeyde and 3- chloro-4-methylpenyl isocyanate,losing two hydrogen atoms.

A mixture of phenylhydrazine (0.216 g,2 mmol) and 3-methyl- benzaldehyde (0.240 g,2 mmol) was stirred at 25 8C for 10 min. Then 3-chloro-4-methylphenylisocyanate (0.335 g,2 mmol) was added to the reaction mixture and in the first method,the reaction mixture was irradiated (ETHOS 1600 Milestone) in a sealed 5 mL vial at 600 W for 15 min and in the second method,the reaction mixture was heated at 250 8C for 1 h. In both methods,the residue was purified by column chromatography using petroleum ether- ethyl acetate (4:1) as the eluent. The solvent was removed,and the productwasobtainedascolorlesscrystals.Thecharacterizationdata of the compounds are given below.

4-(3-Chloro-4-methylphenyl)-5(3-methylphenyl)-2-phenyl- 2,4-dihydro-3H-1,2,-triazol-3-one (4a): Colorless crystals,the yield was 330 mg (88%),Rf = 0.46 (petroleum ether:ethyl acetate, 4:1),mp 168-169 8C,1H NMR (300 MHz,CDCl3): d 2.34 and 2.41 (2s,6H),7.04 (dd,1H,J = 2.1 and 8.1 Hz),7.06 (d,1H,J = 7.5 Hz), 7.19(t,1H,J = 7.6 Hz),7.24(d,1H,J = 7.9 Hz),7.25(t,1H,J = 7.4 Hz), 7.28 (d,1H,J = 7.8 Hz),7.37 (d,1H,J = 2.1 Hz),7.40 (s,1H),7.46 (dd, 2H,J = 8.4 and 7.4 Hz),8.10 (d,2H,J = 7.7 Hz); 13C NMR (75.47 MHz,CDCl3): d 19.88 and 21.35 (2C),118.90,125.09, 125.52 and 125.59 (4C),125.94 (1C),127.76,128.43,12,861, 128.99,131.28and131.44(6C),132.06,134.97,137.09,137.71 and 138.67 (5C),145.17 (1C),151.64 (1C),IR (KBr,cm?1): y 1709 (C55O),1637,1608,1595,1556,1499,1458,1418,1371,1325, 1184,1055,800,758,MS (m/z): 375 (M+),327 (11),208 (20),149 (8),91(100),69 (23),anal.calcd. for C22H18ClN3O (375.5):C,70.30; H,4.83; N,11.18. Found: C,70.15; H,4.93; N,11.04.

5-(4-Chlorophenyl)-2,4-diphenyl-2H-1,2,4-triazol-3(4H)-one (4b): Colorless crystals,the yield was 319 mg (92%),Rf = 0.65 (petroleum ether:ethyl acetate,4:1),mp 176-177 8C, 1H NMR (300 MHz,CDCl3):d 7.26-7.31 (m,3H),7.31 (d,2H,J = 8.8 Hz),7.36 (d,2H,J = 8.8 Hz),7.44-7.52 (m,5H),8.10 (d,2H,J = 7.6),13C NMR (75.47 MHz, CDCl3): d 118.86 (1C),124.80 (1C), 125.66, 127.32,128.93,129.03,129.08,129.22 and 129.70 (7C),133.25, 136.53 and 137.70 (3C),144.18 (1C),151.71 (1C),IR (KBr,cm?1):y 1715(C55O),1639,1619,1599,1497,1427,1369,1321,1150,1095, 831,760,MS (m/z): 347 (M+),228 (13),91 (100),277 (22),anal. calcd. for C20H14ClN3O (347.5): C,69.07; H,4.06; N,12.08. Found: C,68.91; H,4.12; N,12.03.

4-(3-Chloro-4-methylphenyl)-2,5-di(4-methylphenyl)-2H- 1,2,4-triazol-3(4H)-one (4c): Colorless crystals,the yield was 342 mg (88%),Rf = 0.54 (petroleum ether:ethyl acetate,4:1),mp 175-177 8C,1H NMR (300 MHz,CDCl3): d 2.36,2.38 and 2.42 (3s, 3H),7.05 (dd,1H,J = 2.1and8.1 Hz),7.15(d,2H,J = 8.1 Hz),7.25(d, 2H,J = 7.5 Hz),7.28 (d,1H,J = 8.3 Hz),7.31 (d,2H,J = 8.3 Hz),7.37 (d,1H,J = 2.1 Hz),7.96 (d,2H,J = 8.5 Hz),13C NMR (75.47 MHz, CDCl3): d 19.88,20.97 and 21.41 (3C),118.88 (1C),123.28 (1C), 125.58,127.84,127.85,129.36,129.50 and 131.45 (6C),132.21, 134.98,135.22,135.34,137.03 and 140.67 (6C),144.86 (1C), 151.61 (1C),IR (KBr,cm?1): y 1708 and 1695 (C55O),1637,1616, 1512,1427,1371,1326,1151,1053,818,735,MS (m/z): 389 (M+), 105 (89),78 (13),anal. calcd. for C23H20ClN3O (389.5): C,70.86; H, 5.17; N,10.78. Found: C,70.83; H,5.24; N,10.73.

4-(3-Chloro-4-methylphenyl)-2,5-di(4-methylphenyl)-2H- 1,2,4-triazol-3(4H)-one (4c): Colorless crystals,the yield was 342 mg (88%),Rf = 0.54 (petroleum ether:ethyl acetate,4:1),mp 175-177 8C,1H NMR (300 MHz,CDCl3): d 2.36,2.38 and 2.42 (3s, 3H),7.05 (dd,1H,J = 2.1and8.1 Hz),7.15(d,2H,J = 8.1 Hz),7.25(d, 2H,J = 7.5 Hz),7.28 (d,1H,J = 8.3 Hz),7.31 (d,2H,J = 8.3 Hz),7.37 (d,1H,J = 2.1 Hz),7.96 (d,2H,J = 8.5 Hz),13C NMR (75.47 MHz, CDCl3): d 19.88,20.97 and 21.41 (3C),118.88 (1C),123.28 (1C), 125.58,127.84,127.85,129.36,129.50 and 131.45 (6C),132.21, 134.98,135.22,135.34,137.03 and 140.67 (6C),144.86 (1C), 151.61 (1C),IR (KBr,cm?1): y 1708 and 1695 (C55O),1637,1616, 1512,1427,1371,1326,1151,1053,818,735,MS (m/z): 389 (M+), 105 (89),78 (13),anal. calcd. for C23H20ClN3O (389.5): C,70.86; H, 5.17; N,10.78. Found: C,70.83; H,5.24; N,10.73.

4-(3-Chloro-4-methylphenyl)-2-phenyl-5-(4-methyl phenyl)- 2H-1,2,4-triazol-3(4H)-one (4e): Colorless crystals,the yield was 319 mg (85%),Rf = 0.52 (petroleum ether: ethyl acetate,4:1),mp 175-177 8C,1H NMR (300 MHz,CDCl3):d 2.37 and 2.42 (2s,2CH3), 7.05 (dd,CH,J = 2.1 and 8.1 Hz),7.16 (d,2H,J = 8.1 Hz),7.25 (t,1H,J = 7.4 Hz),7.27 (d,1H,J = 8.2 Hz),7.33 (d,2H,J = 8.2 Hz),7.38 (d, 1H,J = 2.1 Hz),7.47 (dd,2H,J = 8.5 and 7.5 Hz),8.11 (d,2H, J = 7.6 Hz),13C NMR (75.47 MHz,CDCl3): d 19.90 and 21.43 (2C), 118.86 (1C),123.20 (1C),125.53,125.60,127.85,127.88,128.98, 129.40 and 131.49 (7C),132.14,135.02,137.12,137.76 and 140.79 (5C),145.09 (1C),151.67 (1C),IR (KBr,cm?1):y 1711 (C55O),1639, 1616,1599,1497,1427,1373,1321,1150,1051,824,750,MS (m/ z): 375 (M+),327 (17),149 (32),91 (71),81 (46),69 (100),57 (55), anal. calcd. for C22H18ClN3O (375.5): C,70.30; H,4.83; N,11.18. Found: C,70.33; H,4.82; N,11.12.

5-(4-Chlorophenyl)-4-phenyl-2-(4-methylphenyl)-2H-1,2,4- triazol-3(4H)-one (4f): Colorless crystals,the yield was 317 mg (88%),Rf = 0.62 (petroleum ether: ethyl acetate,4:1),mp 193- 195 8C, 1H NMR (300 MHz,CDCl3): d 2.39 (s,3H),7.26 (d,2H, J = 7.9 Hz),7.28-7.33 (m,4H),7.36 (d,2H,J = 8.7 Hz),7.42-7.49 (m, 3H),7.97 (d,2H,J = 8.5 Hz),13C NMR (75.47 MHz,CDCl3):d = 20.98 (1C),118.90 (1C),124.89 (1C),127.32,128.90,129.01,129.20, 129.55 and 129.66 (6C),133.32,135.29,135.39 and 136.43 (4C), 143.94 (1C),151.65 (1C),IR (KBr,cm?1): y 1709 and 1690 (C55O), 1639,1610,1515,1427,1377,1153,1100,841,820,MS (m/z): 361 (M+),327 (8),105 (36),91 (12),84 (100),anal. calcd. for C21H16ClN3O (361.5): C,69.71; H,4.46; N,11.61. Found: C, 69.50; H,4.43; N,11.55.

4-Phenyl-2,5-di(4-methylphenyl)-2H-1,2,4-triazol-3(4H)-one (4g): Colorless crystals,the yield was 306 mg (90%),Rf = 0.60 (petroleum ether:ethyl acetate,4:1),mp 192-194 8C, 1H NMR (300 MHz,CDCl3): d 2.35 and 2.39 (2s,6H),7.13 (d,2H,J = 8.0 Hz), 7.25-7.33 (m,6H),7.41-7.48 (m,3H),8.00 (d,2H,J = 8.5 Hz),13C NMR (75.47 MHz,CDCl3): d 20.99 and 21.41 (2C),118.88 (1C), 123.56 (1C),127.38,127.91,128.72,129.26,129.47 and 129.50 (6C),133.66,135.11,135.50 and 140.50 (4C),145.10 (1C),151.79 (1C),IR (KBr,cm?1): y 1707 and 1695 (C55O),1637,1615,1512, 1427,1375,1313,1151,966,816,733,MS (m/z): 341 (M+),105 (10),84(100),anal.calcd. forC22H19N3O(341):C,77.04; H,5.23;N, 12.84. Found: C,76.74; H,5.41; N,12.66.

2,4-Diphenyl-5-(2-methylphenyl)-2H-1,2,4-triazol-3(4H)-one (4h): Colorless crystals,the yield was 267 mg (82%),Rf = 0.66 (petroleum ether:ethyl acetate,4:1),mp: 177-179 8C, 1H NMR (300 MHz,CDCl3):d 2.32 (s,3H),7.11 (d,1H,J = 7.3 Hz),7.18 (t,1H, J = 7.5 Hz),7.22 (d,1H,J = 8.0 Hz),7.28 (d,1H,J = 7.3 Hz),7.30 (dd, 1H,J = 7.9 and 1.7 Hz),7.37 (s,1H),7.44 (m,4H),7.48 (dd,2H, J = 7.6 and 8.3 Hz),8.16 (d,J = 8.8 Hz,2H),13C NMR (75.47 MHz, CDCl3): d 21.34 (1C),118.89,125.17 and 125.50 (3C),126.24 (1C), 127.36,128.36,128.68,128.80,129.01,129.48 and 131.11 (7C), 133.54,137.89 and 138.50 (3C),145.39 (1C),151.83 (1C),IR (KBr, cm?1): y 1705 (C55O),1593,1555,1495,1456,1416,1373,1319, 1148,806,756,690,MS (m/z): 327 (M+),208 (23),91 (98),77 (18), anal. calcd. for C21H17N3O (327): C,77.04; H,5.23; N,12.84. Found: C,76.74; H,5.41; N,12.66.

2,4-Diphenyl-5-(4-methylphenyl)-2H-1,2,4-triazol-3(4H)-one (4i): Colorless crystals,the yield was 297 mg (91%),Rf = 0.68 (petroleum ether:ethyl acetate,4:1),mp 165-166 8C, 1H NMR (500 MHz,CDCl3):d 2.33 (s,3H),7.11 (d,2H,J = 8.0 Hz),7.23 (t,1H, J = 7.4 Hz),7.27-7.30 (m,4H),7.40-7.47 (m,5H),8.12 (d,2H, J = 8.1 Hz),13C NMR (125.8 MHz,CDCl3): d 21.38 (1C),118.84 (1C), 123.49 (1C),125.41,127.38,127.91,128.76,128.95,129.26 and 129.47 (7C),133.60,137.91 and 140.57 (3C),145.31 (1C),151.85 (1C),IR (KBr,cm?1): y 1718 (C55O),1637,1613,1597,1499,1425, 1373,1320,1148,966,824,755,MS (m/z): 327 (M+),312 (19),211 (29),119 (79),105 (31),91 (91),77 (16),anal. calcd. for C21H17N3O (327):C,77.04; H,5.23;N,12.84.Found: C,77.05;H,5.21;N,12.76.

5-(4-Methoxyphenyl)-4-phenyl-2-(4-methylphenyl)-2H-1,2,4- triazol-3(4H)-one (4j): Colorless crystals,the yield was 298 mg (87%),Rf = 0.48 (petroleum ether:ethyl acetate,4:1),m.p. 173- 174 8C, 1H NMR (500 MHz,CDCl3): d 3.78 (s,3H),6.81 (d,2H, J = 8.7 Hz),7.22 (t,1H,J = 7.4 Hz),7.29 (d,2H,J = 7.1 Hz),7.33 (d,2H,J = 8.7 Hz),7.39-7.46 (m,5H),8.10 (d,2H,J = 8.3 Hz),13C NMR (125.8 MHz,CDCl3):d 55.28 (1C),114.01 (1C),118.66 (1C),118.79, 125.34,127.43,128.77,128.93,129.49and129.53(7C),133.64and 137.92 (2C),145.10 (1C),151.83 (1C),161.08 (C-O),IR (KBr,cm?1): y 1707 (C55O),1639,1614,1512,1375,1258,1177,1028,966,837, 760,MS (m/z): 343 (M+),224 (10),209 (12),149 (26),91 (69),81 (50),69 (100),57 (69),anal. calcd. for C21H17N3O2(343): C,73.45; H,4.99; N,12.24. Found: C,73.51; H,4.82; N,12.28.

4-(3-Chloro-4-methylphenyl)-5-(4-chlorophenyl)-2-(4- methylphenyl)-2H-1,2,4-triazol-3(4H)-one (4k): Colorless crys- tals,the yield was 339 mg (83%),Rf = 0.56 (petroleum ether: ethyl acetate,4:1),mp 194-195 8C,1H NMR (300 MHz,CDCl3): d 2.39 and 2.43 (2s,6H),7.04 (dd,1H,J = 2.0 and 8.1 Hz),7.27 (d,2H, J = 8.5 Hz),7.28 (t,1H,J = 7.2 Hz),7.32-7.40 (m,5H),7.94 (d,2H, J = 8.5 Hz),13C NMR (75.5 MHz,CDCl3): d 19.91 and 20.99 (2C), 118.90 (1C),124.63 (1C),125.50,127.79,129.03,129.15,129.56 and131.64(6C),131.87,135.17,135.21,135.50,136.61and137.42 (6C),143.71 (1C),151.47 (1C),IR (KBr,cm?1): y 1697 (C55O),1636, 1605,1504,1427,1377,1151,918,825,727,MS (m/z): 409 (M+), 327 (13),208 (3),105 (23),84 (100),anal. calcd. for C22H17Cl2N3O (409):C,64.40;H,4.18;N,10.24. Found:C,64.32;H,4.27;N,10.18.

3. Results and discussion

Arylhydeazines,benzaldehydes and arylisocyanates undergo a simple reaction under microwave irradiation and solvent-free conditions producing 2,4,5-triary1-2-4-dihydro-3H-1,2,4-triazol- 3-ones 4a-k in 82%-92% yields. This reaction proceeded better under microwave irradiation (the first method),compared to the conventional heating (the second method) in 250 8C for 1 h whose yields are less than 10% and the main product in this method was (E)-1,2,4-triarylesemicarbazides 6 (Table 1),(Scheme 2).

Table 1
Synthesis of 3H-1,2,4-triazol-3-ones 4a-k using microwave irradiation and conventional heating methods.

Scheme 2.A possible mechanism for the formation of products 4.

Mechanistically,it is reasonable to assume that the first step may involve the condensation of arylhydrazine 1 and arylaldehyde 2 to form hydrazone 5 in situ and then the addition of one molecule of isocyanate 3 leads to the formation of semicarbazone 6,which is cyclized to produce 1,2,4-triazolan-3-one 7. Intermediate 7 was finally oxidized under the reaction conditions to produce 2,4- dihydro-3H-1,2,4-triazol-3-ones 4 (Scheme 2).

4. Conclusion

The method reported here offers a simple tandem three- component reaction under microwave irradiation and solvent-free conditions for the preparation of 1,2,4-triazol-3-ones of synthetic and pharmacological interest. The use of commercial starting materials,good yields of the products and fairly short reaction times are the main advantages of this method.


I gratefully acknowledge the financial support from the Research Council of Payame Noor University (PNU),abhar-Iran, and also I wish to thank Mr. Alireza Halvaei.

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