Structure of 1671-88-1
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CAS No. : | 1671-88-1 |
Formula : | C12H10N6 |
M.W : | 238.25 |
SMILES Code : | NN1C(C2=NC=CC=C2)=NN=C1C3=NC=CC=C3 |
MDL No. : | MFCD00075233 |
InChI Key : | VHRKXLULSZZZQT-UHFFFAOYSA-N |
Pubchem ID : | 571203 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.5% | With hydrazine dihydrochloride; hydrazine hydrate; In ethylene glycol; at 130℃; for 6h; | 10.4 g (0.1 mol) of dicyanpyridine powder was added to a 250 mL flask.Further weigh 15g (0.3mol) (85%) hydrazine hydrate and 10.5g (0.1mol) guanidine hydrochloride.Add 100 ml of ethylene glycol to the flask and reflux the reaction in an oil bath at 130 C for 6 h with constant stirring.After a few minutes, the reaction flask was changed from a large amount of pink precipitate to a yellow solution to give an orange-red solution.After the product was cooled to room temperature, the reaction mixture was diluted in 200 ml of distilled water.A large amount of precipitate is quickly produced in the beaker, filtered, washed,After naturally drying, it was recrystallized from ethanol to obtain 10.1 g of white needle crystals.The yield was 84.5%. |
73% | With hydrazine hydrate; sulfur; In ethanol; for 3h;Reflux; | 2-Cyanopyridine (5 mL, 52 mmol) and hydrazine hydrate (8 mL of 50 -60 %) were taken in a round-bottomed flask in 10 mL of absolute ethanol. Sulfur powder (200 mg) was added to the solution and kept under reflux for 3 h. Initially, the solution turned brown and orange crystals start precipitating after 2 h. The crytalline product was filtered, which was air-dried and used without further purification. After that, the orange product was boiled with 2 M HCl solution for 1 h and the initially formed brown solution became colorless. The solution was then cooled and basi- fied with ammonium hydroxide solution and a white curd-like precipitate of 3,5-Di(2-pyridyl)-4-amino-1,2,4-triazole ( L ) was formed. The precipitate was recrystallized from dichloromethane in good yield and used for the next step. Both the ligands L 1 (2-(3,5- di(pyridin-2-yl)-4H-1,2,4-triazol-4-yl)isoindoline-1,3-dione) and L 2 (2,2 -(4-(1H-pyrrol-1-yl)-4H-1,2,4-triazole-3,5-diyl)dipyridine) have been prepared from this common synthon. |
With hydrazine hydrate; In ethanol; at 120℃; for 72h;Autoclave; | 4-amino-3,5-dipyridin-2-yl-4H-1,2,4-triazole (1) and 4-amino-3,5-diphenyl-4H-1,2,4-triazole (2) were synthesized in accordancewith the published procedure and checked with NMR spectra andelemental analysis.Synthesis of 4-amino-3-methyl-5-phenyl-4H-1,2,4-triazole (3)Benzonitrile (2.55 mL, 25 mmol), acetonitrile (2.61 mL, 50 mmol),NH2NH2 . H2O (80%, 9 mL) and anhydrous ethanol (3 mL) were mixedin a 100 mL Teflon-lined autoclave and heated for 3 days at 120 C.After cooling to room temperature the solvent was removed invacuum and the residue was washed with benzene (33mL). Theinsoluble part in benzene was recrystallized from 1-propanol toafford a mixture of three products. Pure samples were obtained bythe separation method using flash Silica Gel chromatography with1-propanol as eluent. Three fractions were collected. First it was 4-amino-3,5-dimethyl-4H-1,2,4-triazole (0.1654 g). The 4-amino-3-methyl-5-phenyl-4H-1,2,4-triazole (1.6782 g) (3) was eluted nextand the 4-amino-3,5-diphenyl-4H-1,2,4-triazole (0.5200 g) (2) wascollected as a third fraction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With acetic acid; In 1,4-dioxane; for 24h;Reflux; | 3, 5-di (pyridin-2-yl)-4H-1, 2, 4-triazol-4-amine (500 mg, 2.1 mmol) was taken in a round-bottom flask and dis- solved in 1, 4-dioxane-acetic acid (1:1) mixture. Next, 2, 5- dimethoxytetrahydrofuran (330 mg, 2.5 mmol) was added and the solution was refluxed for 24 h. After work up the final product L 2 was purified by column chromatography over neutral alumina by 1% ethanol-chloroform eluent. Yield: 484 mg (84%). 1 H NMR (400 MHz, CDCl 3 ): δ(ppm) = 8.42 (2H, d, J = 2.4 Hz, H1 and H1 ), 7.73 (2H, d, J = 3.9 Hz, H4 and H4 ), 7.65 (2H, dt, J = 7.8, 1.0 Hz, H3 and H3 ), 7.20 (2H, dt, J = 4.1, 2.5 Hz, H2 and H2 ), 6.78 (2H, t, J = 1.1 Hz, H5 and H5 ), 6.13 (2H, t, J = 1.1 Hz, H6 and H6 ). FT- IR (KBr, cm -1 ): 1587 (s) ν(C = C), 1466 (m) ν(C = N) (m, medium; s, strong). UV-vis (MeOH) λ(nm) [ ε(M -1 cm -1 )]: 247 [39882], 279 [49890]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In ethanol; water; | General procedure: An ethanolic solution (10mL) of <strong>[1671-88-1]abpt</strong> (95.3mg, 0.4mmol) was added progressively, under continuous stirring, to 10mL of a 1:1 water/methanol solution containing Fe(BF4)2·6H2O (67.5mg, 0.2mmol) and the corresponding salt of K2[M(CN)4] (M=PtII ( 1): 75.5mg, 0.2mmol; M=NiII (2): 48.2mg, 0.2mmol). For both compounds 1 and 2, the resulting red-orange precipitate was filtered off, washed with water and ethanol and then dried. [Fe(<strong>[1671-88-1]abpt</strong>)2(Pt(CN)4)] (1). Yield: 130mg, 78%. Anal. Calc. for C28H20N16FePt: C, 40.4; H, 2.4; N, 26.9. Found: C, 40.2; H, 2.3; N, 27.1%. IR (cm-1): 3225(br), 3179(m), 3142(m), 3079(m), 3051(m), 3019(w), 2164(m), 2132(s), 1633(s), 1609(m), 1588(s), 1568(m), 1541(w), 1521(w), 1490(m), 1461(s), 1426(s), 1402(m), 1340(w), 1301(w), 1289(w), 1276(w), 1256(m), 1167(w), 1147(m), 1116(m), 1082(s), 1057(s), 1038(s), 997(m), 907(w), 894(w), 792(s), 782(s), 755(s), 744(s), 742 (s), 714(w), 693(s), 640(m), 614(m), 526(w), 509(m), 482(m), 451(m). [Fe(<strong>[1671-88-1]abpt</strong>)2(Ni(CN)4)] (2). Yield: 103.0mg, 74%. Anal. Calc. for C28H20N16FeNi: C, 48.4; H, 2.9; N, 32.2. Found: C, 47.8; H, 2.6; N, 32.7%. IR (cm-1): 3237(br), 3178(m), 3080(m), 3054(m), 3019(w), 2151(m), 2121(s), 2082(w), 1631(s), 1609(m), 1589(s), 1569(m), 1541(w), 1523(w), 1492(m), 1462(s), 1428(s), 1402(m), 1340(w), 1302(w), 1290(w), 1278(w), 1258(m), 1157(m), 1147(m), 1117(m), 1085(s), 1058(s), 1039(s), 998(m), 910(w), 895(w), 797(s), 784(s), 757(s), 745(s), 729 (w), 714(w), 694(s), 641(m), 615(m), 532(w), 493(w), 468(m), 455(m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In ethanol; water; | General procedure: An ethanolic solution (10mL) of <strong>[1671-88-1]abpt</strong> (95.3mg, 0.4mmol) was added progressively, under continuous stirring, to 10mL of a 1:1 water/methanol solution containing Fe(BF4)2·6H2O (67.5mg, 0.2mmol) and the corresponding salt of K2[M(CN)4] (M=PtII ( 1): 75.5mg, 0.2mmol; M=NiII (2): 48.2mg, 0.2mmol). For both compounds 1 and 2, the resulting red-orange precipitate was filtered off, washed with water and ethanol and then dried. [Fe(<strong>[1671-88-1]abpt</strong>)2(Pt(CN)4)] (1). Yield: 130mg, 78%. Anal. Calc. for C28H20N16FePt: C, 40.4; H, 2.4; N, 26.9. Found: C, 40.2; H, 2.3; N, 27.1%. IR (cm-1): 3225(br), 3179(m), 3142(m), 3079(m), 3051(m), 3019(w), 2164(m), 2132(s), 1633(s), 1609(m), 1588(s), 1568(m), 1541(w), 1521(w), 1490(m), 1461(s), 1426(s), 1402(m), 1340(w), 1301(w), 1289(w), 1276(w), 1256(m), 1167(w), 1147(m), 1116(m), 1082(s), 1057(s), 1038(s), 997(m), 907(w), 894(w), 792(s), 782(s), 755(s), 744(s), 742 (s), 714(w), 693(s), 640(m), 614(m), 526(w), 509(m), 482(m), 451(m). [Fe(<strong>[1671-88-1]abpt</strong>)2(Ni(CN)4)] (2). Yield: 103.0mg, 74%. Anal. Calc. for C28H20N16FeNi: C, 48.4; H, 2.9; N, 32.2. Found: C, 47.8; H, 2.6; N, 32.7%. IR (cm-1): 3237(br), 3178(m), 3080(m), 3054(m), 3019(w), 2151(m), 2121(s), 2082(w), 1631(s), 1609(m), 1589(s), 1569(m), 1541(w), 1523(w), 1492(m), 1462(s), 1428(s), 1402(m), 1340(w), 1302(w), 1290(w), 1278(w), 1258(m), 1157(m), 1147(m), 1117(m), 1085(s), 1058(s), 1039(s), 998(m), 910(w), 895(w), 797(s), 784(s), 757(s), 745(s), 729 (w), 714(w), 694(s), 641(m), 615(m), 532(w), 493(w), 468(m), 455(m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol; at 60℃; for 2h; | A mixture of <strong>[1671-88-1]4-amino-3,5-bis(2-pyridyl)-1,2,4-triazole</strong> (0.25 g, 0.001 mol) and 9-anthraldehyde (0.20g, 0.001 mol) was refluxed for 2h. The formation of yellow precipitate was filtered, washed with cold methanol and then recrystallized from hot ethanol. Yield: 0.3 g (70%), FT-IR, cm-1(KBr disc): 2875 [s, ν(C-H)], 1628 [vs ν(CH=N)], (br, broad; s, strong; vs very strong). Anal. Calc. for C27H18N6: C, 76.04; H, 4.25; N, 19.71. Found: C, 76.10; H, 4.32; N, 19.62%. EI-MS: 427.12 (M+H+). |
54% | With acetic acid; In methanol; at 85℃; for 6h; | 1.20 mmol of 9-anthracenecarbaldehyde and 1.00 mmol of 3,5-dipyridyl-4-amino-1,2,4-triazole are added to 100 ml of a three neck round bottom flask containing 20 ml of methanol.Under magnetic stirring,Slowly heated to 85 C,When all the ingredients are completely dissolved,Slowly add 3 drops of glacial acetic acid.The reaction was stopped after stirring for 6h at 85 C.The resulting reaction solution was cooled to room temperature,That is, yellow precipitate precipitation,filter,Washed three times with methanol,After drying that is L2,Yield 54%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In methanol; at 25℃; for 2h; | A methanolic solution of Ni(NO3)2·3H2O (0.6g, 0.002mol) was added dropwise to a stirred solution of 4-amino-3,5-bis-(2-pyridyl)-1,2,4-triazole (0.5g, 0.002mol) in methanol. After 2h the light blue precipitate was formed. It was collected by filtration followed by washing with diethyl ether. Yield: 0.75g (79%). FT-IR, cm-1(KBr disc): 3335 [b, ν(O-H)], 3150 [s, ν(N-H)], 2887 [s, ν(C-H)], 1609 [s, ν(CH=N)], 1350 [s, ν(N=O)], 476 [m, ν(Ni-N)]. λmax, nm (ε, M-1cm-1) in H2O: 222(79000), 247(68000), 292(96700), 557(80), 760(40) and 916(80). Anal. Calc. for C24H28N16Ni2O16: C, 31.54; H, 3.09; N, 24.52. Found: C, 31.66; H, 3.17; N, 24.65%. ESI-MS in H2O: (m/z) 394.37 [Ni2L1-2NO3]2+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In methanol; ethanol; for 24h;Reflux; | General procedure: To a solution of the amine (2.90 mmol) in ethanol (10 mL) was slowly added a solution of the corresponding aldehyde (2.90 mmol) in methanol (2 mL). The mixture was refluxed for 24 h and then cooled at room temperature. When a solid did not precipitate, the reaction mixture was evaporated under reduced pressure and gave rise to a solid on standing or on cooling. The resulting product was isolated by filtration, washed successively with cold water, ethanol, and diethyl ether, and recrystallized from ethanol or methanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In methanol; ethanol; for 24h;Reflux; | General procedure: To a solution of the amine (2.90 mmol) in ethanol (10 mL) was slowly added a solution of the corresponding aldehyde (2.90 mmol) in methanol (2 mL). The mixture was refluxed for 24 h and then cooled at room temperature. When a solid did not precipitate, the reaction mixture was evaporated under reduced pressure and gave rise to a solid on standing or on cooling. The resulting product was isolated by filtration, washed successively with cold water, ethanol, and diethyl ether, and recrystallized from ethanol or methanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃; for 1h; | Anhydrous iron(II) acetate (104 mg, 0.60mmol) was added to a colourless suspension of adpt (36mg,0.15 mmol) in acetonitrile (20 ml). The resulting clear orange solution was stirred at room temperature, open to the air for 1 h and then subjected to diethyl ether vapour diffusion. This yielded a few very dark crystals and a large amount of orange powder. The structure of the darkcrystals was determined to be [Fe8(adpt-H)2(OAc)11(O)4(OH)2]*2CH3CN by X-ray crystallography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Nickel(II) acetate tetrahydrate (37 mg, 0.15 mmol) was added to a colourless suspension of adpt (72mg, 0.30 mmol) in acetonitrile (25 ml). The resulting clear yellow solution was stirred at room temperature, open to theair for 30 min and then subjected to diethyl ether vapour diffusion, resulting in the formation of green crystals and some white powder. The structure of the green crystals was determined to be [Ni2(adpt)(adpt-H)(OAc)3(H2O)][Ni(adpt)2(OAc)2]0.5*CH3CN*C4H10Oby X-ray crystallography.ESI-MS (pos.): m/z 533 [Ni2(adpt)(OAc)3],355 [Ni(adpt)(OAc)] and 267 [Ni(adpt)2]2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In methanol; at 20℃; for 2h; | General procedure: Solid adpt (36 mg, 0.15 mmol) was added to a clear, colourless solution of zinc acetate dihydrate (66 mg,0.30 mmol) in methanol (15 ml), and the resulting solution was stirred at room temperature, open to the air for 2 h, during which time it took on a very pale yellow tinge. The solution was then subjected to diethyl ether vapour diffusion, resulting in the formation of very pale yellow crystals, which were structurally characterised by X-ray crystallography. The crystals were isolated by filtration,washed with diethyl ether and dried thoroughly in vacuo. Yield: 58 mg (68%). C36H40N12O14Zn4*H2O: calculated: C37.78, H 3.70, N 14.69; found: C 37.68, H 3.82, N 14.59%.IR (ATR, inter alia): 3519, 3285, 3139, 3076, 1606, 1571,1426, 1412, 796, 699, 667. 1H NMR (CD3CN): 8.82 (d,3J 4.3 Hz, 4H, py-H6), 8.40 (d, 3J 7.5 Hz, 4H, py-H3),8.04 (t, 3J 7.5 Hz, 4H, py-H4), 7.30-7.62 (m, 8H, py-H5,NH2), 1.87 (s, 18 H, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In ethanol; dichloromethane; at 20℃; for 48h; | Co(ClO4)2 (0.08 mM) in ethanol solution (4 mL) was carefully layered on top of dichloromethane solution (4 mL) of L (0.08 mM). The solutions were left for 2 days at room temperature and orange crystals were obtained. Yield: 66%, IR (KBr, cm-1): 3318, 1635, 1608,1591, 1537, 1496, 1459, 1428, 1297, 1258, 1114, 1099, 1090, 1016, 795, 749, 703, 628,424. Anal. Calcd for C32H44Cl4N12O20Co2 (%): C, 32.67; H, 3.77; N, 14.29. Found: C,32.75; H, 3.76; N, 14.31. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In ethanol; dichloromethane; at 20℃; for 48h; | General procedure: Co(ClO4)2 (0.08 mM) in ethanol solution (4 mL) was carefully layered on top of dichloromethane solution (4 mL) of L (0.08 mM). The solutions were left for 2 days at room temperature and orange crystals were obtained. Yield: 66%, IR (KBr, cm-1): 3318, 1635, 1608,1591, 1537, 1496, 1459, 1428, 1297, 1258, 1114, 1099, 1090, 1016, 795, 749, 703, 628,424. Anal. Calcd for C32H44Cl4N12O20Co2 (%): C, 32.67; H, 3.77; N, 14.29. Found: C,32.75; H, 3.76; N, 14.31. |
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