* 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.
With phosphorus pentachloride; ammonia In acetonitrile at -40 - 20℃; for 2 h;
The liquid ammonia (0.5 ml) and acetonitrile (50 ml) at -40 ° C in cold bath, adding pyridine -2,6-dicarboxylic acid (1.67g), to 0 °C, batch by adding phosphorus pentachloride (4g), is omitted, stirring the mixture at room temperature for 2 hours, the response finishes, concentrated under reduced pressure, the residue is dissolved with methylene chloride, washed with saturated sodium bicarbonate to neutral, anhydrous magnesium sulphate dried, concentrated, precipitated solid, the resulting solid is recrystallized with isopropyl alcohol, to obtain white crystal of 2,6-di-cyano pyridine (1.13g). The yield is 88percent.
Reference：
[1] Patent: CN105503716, 2016, A, . Location in patent: Paragraph 0016
[2] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[3] Chemical Communications, 2017, vol. 53, # 42, p. 5718 - 5720
5
[ 499-83-2 ]
[ 1195-59-1 ]
Yield
Reaction Conditions
Operation in experiment
51.1%
Stage #1: With sodium tetrahydroborate In ethanol for 10 h; Inert atmosphere; Schlenk technique; Reflux Stage #2: Inert atmosphere; Schlenk technique; Reflux
Asolution of 2,6-pyridinedicarboxylic acid (3.30 g) in absolute ethyl alcohol (60 mL) was added NaBH4 (4.01 g) dropwise under stirred in ice-salt baths. After2 h, refluxed for 10 h following stirred at the room temperature for 3 h, the reaction mixture was evaporated under reduced pressure. Then, acetone was added (20 mL), and solution was refluxed and evaporated again. After cooling to room temperature, potassium carbonate solution (20 mL) and water were added, and the reaction mixture was extracted with CHCl3. The collected organic layers were dried over NaSO4, filtered and evaporated under reduced pressure to give a pale white acicular crystal (the yield was 1.20 g (51.1percent); m.p. = 115.6–116.7°C).
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6
[ 499-83-2 ]
[ 7703-74-4 ]
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7
[ 499-83-2 ]
[ 499214-11-8 ]
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8
[ 499-83-2 ]
[ 1197-10-0 ]
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9
[ 499-83-2 ]
[ 69950-65-8 ]
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10
[ 499-83-2 ]
[ 39977-44-1 ]
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[ 67-56-1 ]
[ 499-83-2 ]
[ 7170-36-7 ]
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[7] Patent: WO2006/117754, 2006, A1, . Location in patent: Page/Page column 50-51
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[ 499-83-2 ]
[ 7170-36-7 ]
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[13] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9493 - 9504
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[15] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7267 - 7283
13
[ 67-56-1 ]
[ 499-83-2 ]
[ 5453-67-8 ]
[ 7170-36-7 ]
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[1] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4914 - 4920
[2] Journal of Organometallic Chemistry, 1980, vol. 186, # 2, p. 147 - 153
14
[ 499-83-2 ]
[ 4722-94-5 ]
Reference：
[1] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1991, # 11, p. 3049 - 3054
15
[ 499-83-2 ]
[ 64-17-5 ]
[ 15658-60-3 ]
Yield
Reaction Conditions
Operation in experiment
92%
at -20 - 20℃; for 6 h;
Thionyl chloride (360 mg, 3 mmol) was added dropwise to a solution of pyridine-2,6-dicarboxylate (170 mg, 1 mmol) (2) in EtOH (5 mL) at -20 oC and then the mixture was stirred at room temperature for 6 h. The solvent was evaporated and the residue was taken up in methylene chloride, dried by MgSO4 and evaporated. The product was obtained following purification by silica gel column chromatography as a colorless solid powder 4 (205 mg, yield 92percent).
82.35%
Stage #1: for 8 h; Reflux Stage #2: at 20℃; for 8 h;
60 g (359.02 mmol) of pyridine-2,6-dicarboxylic acid and 250 mL (3446. 54 mmol) of S0C12 were added to a 1000 mL round bottom flask and mixed, After refluxing for 8 h, S0C12 was distilled off, and then 300 mL (5140.76 mmol) of absolute ethanol was added dropwise under ice-cooling. The mixture was stirred at room temperature for 8 hours and then concentrated to dryness. The residue was washed with 300 mL of water and then treated with potassium carbonate Adjusted to pH 7 and then extracted three times with 150 mL of methylene chloride. The organic phases were combined and the organic phase was washed with 200 mL of saturated brine, And dried over anhydrous sodium sulfate, filtered and dried to give 66 g (295. 66 mmol) of the yellowish crystalline solid, pyridine-2,6-dicarboxylic acid diethyl ester, in 82.35percent yield;
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[3] Tetrahedron Letters, 2017, vol. 58, # 10, p. 991 - 994
[4] Molecular Crystals and Liquid Crystals, 2007, vol. 470, # 1, p. 369 - 381
[5] Organometallics, 2015, vol. 34, # 7, p. 1170 - 1176
[6] Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2014, vol. 78, # 1-4, p. 151 - 159
[7] Synthetic Communications, 2009, vol. 39, # 24, p. 4429 - 4440
[8] Synthetic Communications, 2005, vol. 35, # 17, p. 2317 - 2324
[9] Patent: CN104193673, 2016, B, . Location in patent: Paragraph 0070-0071
[10] Inorganic Chemistry, 2012, vol. 51, # 9, p. 5199 - 5207
[11] Dalton Transactions, 2012, vol. 41, # 48, p. 14480 - 14483
[12] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1955, vol. 3, p. 55,58[13] Chem.Abstr., 1956, # 7800,
[14] Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6852 - 6864
[15] Patent: WO2006/66968, 2006, A1, . Location in patent: Page/Page column 36-37
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[17] Australian Journal of Chemistry, 2009, vol. 62, # 9, p. 1130 - 1136
[18] Chemistry - A European Journal, 2013, vol. 19, # 50, p. 17141 - 17149
[19] RSC Advances, 2016, vol. 6, # 109, p. 107305 - 107309
[20] New Journal of Chemistry, 2018, vol. 42, # 11, p. 8567 - 8576
16
[ 499-83-2 ]
[ 15658-60-3 ]
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[2] Chemicke Listy, 1945, vol. 48, p. 869,871[3] Chem.Abstr., 1955, p. 9665
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[5] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 8, p. 1127 - 1136
[6] Journal of the American Chemical Society, 1982, vol. 104, # 8, p. 2251 - 2257
[7] Australian Journal of Chemistry, 1991, vol. 44, # 8, p. 1041 - 1048
[8] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2011, vol. 79, # 2, p. 348 - 355
[9] Tetrahedron, 2011, vol. 67, # 44, p. 8458 - 8464
[10] RSC Advances, 2016, vol. 6, # 34, p. 28194 - 28199
17
[ 499-83-2 ]
[ 64-17-5 ]
[ 21855-16-3 ]
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[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 5061 - 5074
[0118] 36 mg (0.1524 mmol) <strong>[298-46-4]carbamazepin</strong>e and 26 mg (0.1556 mmol) 2,6-pyridinedicarboxylic acid were dissolved in approximately 2 mL ethanol. Slow evaporation of the solvent yielded clear needles of a 1:1 <strong>[298-46-4]carbamazepin</strong>e/2,6-pyridinedicarboxylic acid cocrystal, as shown in FIG. 14B. [0119] Crystal data: (Bruker SMART-APEX CCD Diffractometer). C22H17N3O5, M=403.39, orthorhombic P2(1)2(1)2(1); a=7.2122, b=14.6491, c=17.5864 , alpha=90, beta=90, gamma=90, V=1858.0(2) 3, T=100 K, Z=4, mu(MO-Kalpha)=0.104 mm, Dc=1.442 Mg/m3, lambda=0.71073 3, F(000)840, 2thetamax=28.3.116641 reflections measured, 4466 unique (Rint=0.093). Final residuals for 271 parameters were R1=0.0425 and wR2=0.0944 for I>2?(I). [0120] Crystal packing: Each hydrogen on the CBZ 1 amine is hydrogen bonded to a carbonyl group of a different 2,6-pyridinedicarboxylic acid moiety. The carbonyl of the CBZ carboxamide is hydrogen bonded to two hydroxide groups of one 2,6-pyridinedicarboxylic acid moitey. [0121] Infrared Spectroscopy: (Nicolet Avatar 320 FTIR). 3439 cm-1, (N-H stretch, 1 amine, CBZ); 1734 cm-1, (CO); 1649 cm-1, (CC). [0122] Melting Point: 214-216 C. (MEL-TEMP). (<strong>[298-46-4]carbamazepin</strong>e m.p.=191-192 C., 2,6-pyridinedicarboxylic acid m.p.=248-250 C.). [0123] Thermogravimetric Analysis: (TA Instruments 2950 Hi-Resolution TGA). 69% weight loss starting at 215 C. and a 17% weight loss starting at 392 followed by complete decomposition.
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;Reflux;
The synthesis of pyridine acyl sulfonamide derivatives was followed the general reaction pathway outlined in refPreviewPlaceHolderScheme 1. Compounds 1-24 were synthesized by coupling substituted benzenesulfonamide with nicotinic acid, isonicotinic acid, picolinic acid, pyridine-2,6-dicarboxylic acid or pyridine-3,5-dicarboxylic acid, using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 4-dimethylaminopyridine (DMAP) as condensing agent. The mixture was refluxed in anhydrous CH2Cl2 for 8-10 h. The products were extracted with ethyl acetate. The extract was washed successively with HCl, NaHCO3 and water, dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography using petroleum ether and ethyl acetate (1:1).
General procedure: 1 mmol of Cu(CH3COO)2·H2O in 10 mL of water was added dropwise to a mixed-ligand solution of 2,6-pyridinedicarboxylic acid (1 mmol) and the appropriate pyrimidine ligand (1 mmol) in 20 mL of water with stirring at room temperature. The solution was filtered and left standing at ambient temperature. After a few days blue crystals appeared. These were washed and dried at room temperature. Crystals for X-ray diffraction were used directly from the mother liquid. Yield ca. 75-85%. Elemental Anal. Calc. for C11H15CuN3O9 (1): C, 33.3; H, 3.8; N, 10.6. Found: C, 33.4; H, 3.9; N, 10.6%; for C11H9CuN5O7 (2): C, 34.2; H, 2.3; N, 18.1. Found: C, 34.1; H, 2.2; N, 18.1%; for C11H11ClCuN4O6 (3): C, 33.5; H, 2.8; N, 14.2. Found: C, 33.5; H, 2.7; N, 14.3%.
[H3O][Cr(2,6-pyridinedicarboxylate)2] [H3O+.Cl-][ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
With sodium hydroxide; In ethanol; water; for 12h;Reflux;
Dipicolinic acid (H2dipic, 0.167 g, 1.0 mmol) and NaOH (0.080 g, 2.0.mmol) were dissolved in the mixture of ethanol/water (20 mL) and dropwise added, under continuous stirring, to an aqueous solution (5 mL) of CrCl3·6H2O (0.988 g,0.50 mmol). Then <strong>[1115-70-4]metformin hydrochloride</strong> (0.057 g, 0.50 mmol) was added to the resulting mixture and was refluxed for 12 h, filtered off and then left to evaporate in a beaker in air at the ambient temperature. In an attempt to prepare the complex [MetH][Cr(dipic)2], after 5 day, dark purple crystals suitable for X-ray structural analysis from the title complex, (1) , were obtained. The yield was 65 %. Anal. Calc. for C14H12ClCrN2O10: C, 36.90; H, 2.65; N, 6.15. Found: C,36.7; H, 2.80; N, 5.9 %. IR (KBr) (nu, cm-1): 3599 (w), 3558(m), 3474 (m), 3423 (m), 3078 (m), 3049 (m), 2923 (w),1673 (s), 1598 (w ), 1479 (w), 1428 (m), 1332 (s), 1261 (w), 1169 (s), 1090 (s), 1036 (w), 1010 (w), 920 (s), 854 (w),779(s ), 750(s), 682 (s), 593 (w), 541 (w), 452 (s). UV-vis (aqueous solution) (nu, nm): 260, 267, 301, 352, 551.
7H2O*C5H5N*C21H9CeN3O12(3-)*3H(1+)*C5H12N2O2[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
General procedure: For (H2His)(HPy)[Ce(dpc)3].4H2O (4) and (H2Orni)(HPy)[Ce(dpc)3].7H2O (5), to a solution of dipicolinic acid (0.50 g,3 mmol) in methanol (10 mL), a solution of Ce(NO3)3.6H2O(0.434 g, 1 mmol in 10 mL methanol) was added. The reactionmixture was stirred for half an hour to obtain a deep yellow precipitate.To the reaction mixture 10 mL solution of L-histidinehydrochloride (0.21 g, 1 mmol) or <strong>[3184-13-2]L-ornithine hydrochloride</strong> (0.17 g, 1 mmol) in water was added in small portions andstirred. Minimum amount of pyridine (py) was added to dissolvethe precipitate once the color of the precipitate changed tolight yellow. This led to dissolution of the precipitate to result a reddish yellow solution. The reaction mixture was filtered andleft for crystallization. After three days reddish yellow crystals were obtained.
General procedure: For (H2Arg)[Ce(dpc)3].7H2O (1), (H2His)[Ce(dpc)3].4H2O(2), and (H2Orni)[Ce(dpc)3].7H2O (3), to a solution of dipicolinicacid (0.501 g, 3 mmol) in methanol (10 mL), a solution of(NH4)2Ce(NO3)6 (0.548 g, 1 mmol) in methanol (10 mL) wasadded. The reaction mixture was stirred for 30 min and a yellowprecipitate was obtained. To the reaction mixture 10 mL solutionof L-arginine hydrochloride (0.21 g, 1 mmol) or L-histidinehydrochloride (0.21 g, 1 mmol) or <strong>[3184-13-2]L-ornithine hydrochloride</strong>(0.17 g, 1 mmol) in water was added in small portions andstirred. The respective precipitate obtained was dissolved inwater to obtain a yellow solution. The yellow solution was filteredand left for crystallization. After four days light yellowcrystals were obtained.
4H2O*C5H5N*C21H9CeN3O12(3-)*3H(1+)*C6H9N3O2[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
General procedure: For (H2His)(HPy)[Ce(dpc)3].4H2O (4) and (H2Orni)(HPy)[Ce(dpc)3].7H2O (5), to a solution of dipicolinic acid (0.50 g,3 mmol) in methanol (10 mL), a solution of Ce(NO3)3.6H2O(0.434 g, 1 mmol in 10 mL methanol) was added. The reactionmixture was stirred for half an hour to obtain a deep yellow precipitate.To the reaction mixture 10 mL solution of L-histidinehydrochloride (0.21 g, 1 mmol) or L-ornithine hydrochloride (0.17 g, 1 mmol) in water was added in small portions andstirred. Minimum amount of pyridine (py) was added to dissolvethe precipitate once the color of the precipitate changed tolight yellow. This led to dissolution of the precipitate to result a reddish yellow solution. The reaction mixture was filtered andleft for crystallization. After three days reddish yellow crystals were obtained. For complex 4: Isolated yield (based on metal)70%. Elemental Anal. Calcd. for C32H37CeN7O18: C, 40.51; H,3.90; Found C, 40.57; H, 3.99. IR (KBr, cm-1): 3391 (bs), 1714(s), 1614 (s), 1428 (w), 1385 (s), 1366 (m), 1273 (w), 1188(w), 1076 (m), 765 (w). [alpha]D25 = + 7.2. Molar conductance:436.5 Scm2mol-1 in water. Magnetic moment mueff. at 298 K:1.98 BM.
General procedure: For (H2Arg)[Ce(dpc)3].7H2O (1), (H2His)[Ce(dpc)3].4H2O(2), and (H2Orni)[Ce(dpc)3].7H2O (3), to a solution of dipicolinicacid (0.501 g, 3 mmol) in methanol (10 mL), a solution of(NH4)2Ce(NO3)6 (0.548 g, 1 mmol) in methanol (10 mL) wasadded. The reaction mixture was stirred for 30 min and a yellowprecipitate was obtained. To the reaction mixture 10 mL solutionof <strong>[1119-34-2]L-arginine hydrochloride</strong> (0.21 g, 1 mmol) or L-histidinehydrochloride (0.21 g, 1 mmol) or L-ornithine hydrochloride(0.17 g, 1 mmol) in water was added in small portions andstirred. The respective precipitate obtained was dissolved inwater to obtain a yellow solution. The yellow solution was filteredand left for crystallization. After four days light yellowcrystals were obtained.For complex 1: Isolated yield (based on metal) 55%. ElementalAnal. Calcd. for C27H32CeN7O21: C, 34.81; H, 3.43; FoundC, 34.57; H, 3.36. IR (KBr, cm-1): 3365 (bs), 1639(s), 1465(m),1423 (m), 1360 (s), 1268 (w), 1176 (w), 1073(m), 1024 (m), 920(w). [alpha]D25 = + 7.5. Molar conductance: 430.3 Scm2mol-1 in water.
General procedure: For (H2Arg)[Ce(dpc)3].7H2O (1), (H2His)[Ce(dpc)3].4H2O(2), and (H2Orni)[Ce(dpc)3].7H2O (3), to a solution of dipicolinicacid (0.501 g, 3 mmol) in methanol (10 mL), a solution of(NH4)2Ce(NO3)6 (0.548 g, 1 mmol) in methanol (10 mL) wasadded. The reaction mixture was stirred for 30 min and a yellowprecipitate was obtained. To the reaction mixture 10 mL solutionof L-arginine hydrochloride (0.21 g, 1 mmol) or L-histidinehydrochloride (0.21 g, 1 mmol) or L-ornithine hydrochloride(0.17 g, 1 mmol) in water was added in small portions andstirred. The respective precipitate obtained was dissolved inwater to obtain a yellow solution. The yellow solution was filteredand left for crystallization. After four days light yellowcrystals were obtained.
With phosphorus pentachloride; ammonia; In acetonitrile; at -40 - 20℃; for 2h;
The liquid ammonia (0.5 ml) and acetonitrile (50 ml) at -40 C in cold bath, adding pyridine -2,6-dicarboxylic acid (1.67g), to 0 C, batch by adding phosphorus pentachloride (4g), is omitted, stirring the mixture at room temperature for 2 hours, the response finishes, concentrated under reduced pressure, the residue is dissolved with methylene chloride, washed with saturated sodium bicarbonate to neutral, anhydrous magnesium sulphate dried, concentrated, precipitated solid, the resulting solid is recrystallized with isopropyl alcohol, to obtain white crystal of 2,6-di-cyano pyridine (1.13g). The yield is 88%.
3 was produced by refluxing a mixture of adefovir (27.3 mg,0.1 mmol) and 2, 6-pyridine dicarboxylic acid (16.7 mg, 0.1 mmol) at 90C in 8 mL of ethanol-water (1:1, v/v) for about 3 h, the resulting mixtures were filtered, and the filtrate was placed at room temperature for 5 days. The colorless block crystals were obtained in 75% yield.
4,6-diaminoresorcinol-2,6-pyridinedicarboxylic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium hydroxide; In water; at 90℃; for 0.166667h;
Into a 1000 mL glass flask, equipped with a mechanical stirrer and a nitrogen inlet/outlet, were placed 400 mL water. 4,6-diaminoresorcinol dihydrochloride (4.26 g, 0.02 mol) was added. One equimolar amount of 2,6-pyridinedicarboxylic acid (PDA, 0.02 mol) dissolved in NaOH (0.04 mol) aqueous solution was slowly added. Afterwards, the mixture was heated to 90 C for 10 min and DAR-PDA salt solid precipitated, then the product was collected in nitrogen atmosphere. The product was dried under vacuum at 60 C for 48 h.
General procedure: All chemicals used in this study were obtained from commercial suppliers (Sigma-Aldrich) and were used without any further purification. The spectroscopic grade solvents employed for the crystallization purpose were of the highest available purity. All the molecular complexes were prepared by dissolving <strong>[230-07-9]4,7-phenanthroline</strong> (1) and the corresponding carboxylic acids in a solution of dimethylsulfoxide (DMSO), as listed in Chart 1, in a 1:1 ratio and then by slow evaporation of the solution at ambient conditions. Single crystals were obtained within 48h in all the cases. In a typical example, 18.3mg (0.97mmol) of 1 and 16.6mg (0.99mmol) of pyridine-2,6-dicarboxylic acid, a, were dissolved by heating up to 80C in 2mL DMSO and allowed for slow evaporation at ambient conditions. Good quality single crystals suitable for X-ray diffraction study were obtained in 48h.
With ammonium hydroxide; In N,N-dimethyl-formamide; at 20℃;Darkness;
The synthesis of 2 was similar to that of 1, but with H2pda(33.4 mg, 0.2 mmol) in place of H2pca. The resultant solution wasallowed to evaporate slowly in darkness at room temperature forseveral days to afford the product as block-shaped pink crystalsof 2. (Yield: 69%, based on silver). Anal. Calc. (found) for Ag2C12H10N4O6: C, 27.72 (27.69); H, 1.55 (1.61); N, 10.78 (10.96)%. IR (KBr): m(cm1) = 3395 (m), 3326 (m), 3211 (m), 3058 (m), 1664 (s), 1613(s), 1562 (s), 1428 (m), 1371 (s), 1268 (m), 1167 (w), 1046 (w),1021 (m), 900 (w), 816 (m), 753 (m), 715 (s), 651 (m), 619 (m),575 (w), 511 (w), 448 (w).
With sodium hydroxide; In methanol; water; at 38℃; for 0.833333h;Reflux;
1) adding pyridinedicarboxylic acid, sodium hydroxide and <strong>[1115-70-4]metformin hydrochloride</strong> in an organic solvent at a molar ratio of 2: 5: 1,And the mixture was dissolved at a temperature of 38 C, and the organic solvent was a mixture of water and methanol in a molar ratio of 1: 1.5, and the mixture of water and methanol was 12 times the volume of the mixture of pyridinedicarboxylic acid, sodium hydroxide and <strong>[1115-70-4]metformin hydrochloride</strong>;2) Chromium chloride was dissolved in methanol at a molar ratio of chromium chloride to methanol of 1: 7, and the solution of chromium chloride was slowly added dropwise to the solution in Step 1) and heated to reflux for 50 min to stop the reaction , Standing for 12h, filtration, the red filtrate;3) Place the red filtrate at room temperature,Dark,Naturally volatile for half a month,To obtain purple crystal is dimethyl metformin pyridine dicarboxylic acid Cr (III) complex.
Vanadyl sulfate (434mg, 2.0mmol) was dissolved in 40mL of water. Solid 2,6- pyridinedicarboxylic acid (334mg, 2.0mmol) then was added. The mixture was stirred at 90C until the green solution was obtained. Afterward, solid <strong>[1115-70-4]metformin hydrochloride</strong> (165mg, 1.0mmol) was added to the resulting mixture and was heated at 90C for 30min until dissolution was complete. After 2 days, the white precipitated H2dipic ligand excess and blue crystalline 1 were filtered off. 10mL water was again added to the filtrate and was heated at 90C for 30min. After several weeks, dark crystals of the complex 2, suitable for X-ray structural analysis, were obtained. During this period the color of the solution changed to dark blue. Anal. Calc. for C18H19N7O12V2: C, 34.47; H, 3.05; N, 15.63. Found: C, 34.27; H, 2.69; N, 15.54%. 1H NMR (DMSO-d6): delta=2.95 (s, 6H, CH3, H2Met2+), 8.17 (s, 2H, dipic2-), 8.49 (s, 1H, dipic2-) ppm. 13C NMR (DMSO-d6): delta=36.2 (CH3, H2Met2+), 124.8 (dipic2-), 145.2 (dipic2-), 146.2 (dipic2-), 152.7 (H2Met2+), 153.8 (H2Met2+), 165.6 (dipic2-) ppm. FT-IR (KBr): 3410, 3330, 3182 nu(N-H), 3081 nu(aromatic C-H), 2922 nuas (aliphatic C-H), 2852 nus (aliphatic C-H), 1689 nuas (CO2-), 1658, 1341 nus (CO2-), 1172, 1076, 936, 862, 767, 674, 456cm-1. UV-Vis (aqueous solution) (lambda, nm): 207, 274.
Vanadyl sulfate (434mg, 2.0mmol) was dissolved in 40mL of water. Solid 2,6- pyridinedicarboxylic acid (334mg, 2.0mmol) then was added. The mixture was stirred at 90C until the green solution was obtained. Afterward, solid <strong>[1115-70-4]metformin hydrochloride</strong> (165mg, 1.0mmol) was added to the resulting mixture and was heated at 90C for 30min until dissolution was complete. After 2 days, the white precipitated H2dipic ligand excess and blue crystalline 1 were filtered off. 10mL water was again added to the filtrate and was heated at 90C for 30min. After several weeks, dark crystals of the complex 2, suitable for X-ray structural analysis, were obtained. During this period the color of the solution changed to dark blue. Anal. Calc. for C18H19N7O12V2: C, 34.47; H, 3.05; N, 15.63. Found: C, 34.27; H, 2.69; N, 15.54%. 1H NMR (DMSO-d6): delta=2.95 (s, 6H, CH3, H2Met2+), 8.17 (s, 2H, dipic2-), 8.49 (s, 1H, dipic2-) ppm. 13C NMR (DMSO-d6): delta=36.2 (CH3, H2Met2+), 124.8 (dipic2-), 145.2 (dipic2-), 146.2 (dipic2-), 152.7 (H2Met2+), 153.8 (H2Met2+), 165.6 (dipic2-) ppm. FT-IR (KBr): 3410, 3330, 3182 nu(N-H), 3081 nu(aromatic C-H), 2922 nuas (aliphatic C-H), 2852 nus (aliphatic C-H), 1689 nuas (CO2-), 1658, 1341 nus (CO2-), 1172, 1076, 936, 862, 767, 674, 456cm-1. UV-Vis (aqueous solution) (lambda, nm): 207, 274.
[mono-protonated 6-phenyl-1,3,5-triazine-2,4-diamine][Fe(2,6-pyridinedicarboxylate)2]3H2O[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
To a solution of 2,6-pyridinedicarboxylicacid (0.167 g, 1.0 mmol) in methanol (10 ml), a solutionof anhydrous ferric chloride (0.053 g, 0.33 mmol) in methanol(10 ml) was added. A brown precipitate was obtained after stirring for half an hour. The precipitate was dissolved by adding 20 ml water and to this solution 6-phenyl-1,3,5-triazine-2,4-diamine (0.094 g, 0.5 mmol) was added. The reaction mixture was stirredfor 3 h at room temperature. Further standing for 4 days at room temperature resulted in crystals of 1. Isolated yield: (0.220 g) 70%. Elemental Anal. Calc. for C23H22N7O11Fe: C, 43.97; H, 3.53;N, 15.60; Found: C, 43.96; H, 3.50; N, 15.59%. IR (KBr, cm-1):3390 (m), 3140 (w), 3087 (s), 3048 (w), 1661 (s), 1609 (w), 1570(s), 1528 (m), 1427 (m), 1331 (s), 1169 (s), 1082 (s), 1027 (m),912 (s), 862 (w), 777 (m), 745 (s), 681 (s), 590 (w). Magnetic moment (28 C): 5.37 BM. UV-Vis (methanol, nm (epsilon, mol-1cm-1)): 212 (8210), 280 (3130), 720 (13).
[Cu(pyrazinecarboxamide)(dipicolinate)(H2O)].H2O}[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85%
The synthesis of the compound [Cu(pca)(dipic)(H2O)]H2O}was proceeded in the following manner: to a water solution of copper(II) acetate monohydrate (0.15 g, 0.75 mmol) was added a stoichiometric amount of N-donor ligand pyrazinecarboxamide (0.09g, 0.75 mmol). The mixture was stirred for half an hour at laboratory temperature to obtain a homogeneous solution, then further reacted with stoichiometric ratio 1:1 of dipicolinic acid (0.125 g,0.75 mmol) and heated. The resulting blue solution was cooled down to the ambient temperature, filtered and left to slowly evaporate at laboratory temperature, what after a few days resulted in the single-crystals formation of targeted compound. Single-crystals for X-ray diffraction analysis were used directly from mother liquid.IR (ATR, cm-1): 3483(m), 3450(m), 3350(m), 3208(m), 3080(w),3043(w), 1688(s), 1673(s), 1634(s), 1606(s), 1593(s), 1527(w),1429(w), 1383(m), 1360(s), 1347(s), 1269(w), 1172(m), 1163(m),1088(m), 1080(m), 1022(m), 912(m), 883(w), 866(w), 781(s), 739(m), 705(w), 685(m), 633(m), 569(m), 515(w), 461(s), 440(s)UV-Vis (nm): 206, 274, 691.Elemental analysis for complex 1 (C12H12CuN4O7, Mw = 387.79g mol1) found % (expected %): C 36.99 (37.17); N 14.77 (14.45); H3.12 (3.12). Yield: 85%.
[Cu(N-methylnicotinamide)(dipicolinate)(H2O)].2H2O}[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
General procedure: The synthesis of the compound [Cu(pca)(dipic)(H2O)]H2O}was proceeded in the following manner: to a water solution of copper(II) acetate monohydrate (0.15 g, 0.75 mmol) was added a stoichiometric amount of N-donor ligand pyrazinecarboxamide (0.09g, 0.75 mmol). The mixture was stirred for half an hour at laboratory temperature to obtain a homogeneous solution, then further reacted with stoichiometric ratio 1:1 of dipicolinic acid (0.125 g,0.75 mmol) and heated. The resulting blue solution was cooled down to the ambient temperature, filtered and left to slowly evaporate at laboratory temperature, what after a few days resulted in the single-crystals formation of targeted compound. Single-crystals for X-ray diffraction analysis were used directly from mother liquid.
[Cu(N-(hydroxymethyl)nicotinamide)(dipicolinate)(H2O)]2.2[Cu(N-(hydroxymethyl)nicotinamide)(dipicolinate)(H2O)2].4H2O}[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73%
General procedure: The synthesis of the compound [Cu(pca)(dipic)(H2O)]H2O}was proceeded in the following manner: to a water solution of copper(II) acetate monohydrate (0.15 g, 0.75 mmol) was added a stoichiometric amount of N-donor ligand pyrazinecarboxamide (0.09g, 0.75 mmol). The mixture was stirred for half an hour at laboratory temperature to obtain a homogeneous solution, then further reacted with stoichiometric ratio 1:1 of dipicolinic acid (0.125 g,0.75 mmol) and heated. The resulting blue solution was cooled down to the ambient temperature, filtered and left to slowly evaporate at laboratory temperature, what after a few days resulted in the single-crystals formation of targeted compound. Single-crystals for X-ray diffraction analysis were used directly from mother liquid.
[Co<SUB>2</SUB>(4,4'-bis(1-imidazolyl)biphenyl)(2,6-pyridinedicarboxylate)<SUB>2</SUB>(water)<SUB>4</SUB>][ No CAS ]
Yield
Reaction Conditions
Operation in experiment
62%
General procedure: To a solution of the pyridinedicarboxylic acid (0.084g, 0.5 mmol) in distilled water (8 mL), NaOH (0.040 g, 1.0 mmol) was added and stirred for 5 min. Then the hexahydrated metal nitrate salt (0.5 mmol) and <strong>[855766-92-6]4,4′-bis(1-imidazolyl)biphenyl</strong> (0.143 g, 0.5 mmol) were added. The mixture was placed and sealed in a Teflon-lined stainless steel vessel (10 mL), heated at 160C for 3 days and cooled to room temperature with the rate of 0.06C/min. The obtained crystals were filtered, washed with water and ethanol then dried in air. [Co2(BIBP)(2,6-PDC)2(H2O)4] (1) The preparation of (1) was done according to the general procedure using 2,6-pyridinedicarboxylic acid and Co(NO3)2·6H2O (0.146 g, 0.5 mmol). Yield: 0.250 g, 62%. Anal. Calc. for C32H28N6O12Co2: C, 47.66; H, 3.50; N, 10.42. Found: C, 47.91; H, 3.76; N, 10.70%. FT-IR ( ν/cm-1): 3676 m, 3291 br, 3166 m, 3126 m, 2989 m, 2902 m, 1636 s, 1608vs, 1592 s,1576 s, 1520 s,1467 m, 1433 m, 1417 m, 1378 s, 1362 vs, 1343 m, 1311 m, 1281 m, 1268 m, 1255 m, 1195 m,1181 m, 1133 m, 1106 m, 1070 vs, 1036 m, 1003 m, 963 m, 944 m, 913 m, 862 w, 834 s, 822 m, 768 w, 747 s, 736 s, 722 m, 689 m, 673 m.
1D-[Zn(4,4'-bis(1-imidazolyl)biphenyl)(2,6-pyridinedicarboxylate)]*4.5(water)}<SUB>n</SUB>[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74%
General procedure: To a solution of the pyridinedicarboxylic acid (0.084g, 0.5 mmol) in distilled water (8 mL), NaOH (0.040 g, 1.0 mmol) was added and stirred for 5 min. Then the hexahydrated metal nitrate salt (0.5 mmol) and <strong>[855766-92-6]4,4′-bis(1-imidazolyl)biphenyl</strong> (0.143 g, 0.5 mmol) were added. The mixture was placed and sealed in a Teflon-lined stainless steel vessel (10 mL), heated at 160C for 3 days and cooled to room temperature with the rate of 0.06C/min. The obtained crystals were filtered, washed with water and ethanol then dried in air. 3.3.3 1D-[Zn(BIBP)(2,6-PDC)]∙4·.5H2O}n (3) The preparation of (3) was done according to the general procedure using 2,6-pyridinedicarboxylic acid and Zn(NO3)2·6H2O (0.148 g, 0.5 mmol). Yield: 0.220 g, 74%. Anal. Calc. for C25H26N5O8,5Zn: C, 50.22; H, 4.38; N, 11.71. Found: C, 50.16; H, 4.22; N, 11.92%. FT-IR (ν/cm-1): 3373 br, 3138 m, 2989 m, 2902 m, 1627 vs, 1593 s, 1575 m, 1521 vs, 1429 m, 1371 s, 1338 m, 1313 m, 1280 m, 1247 m, 1186 m, 1130 s, 1113 m, 1071 vs, 1036 m, 1008 m, 968 m, 953 m, 912 m, 857 w, 826 s, 774 m, 765 m, 731 m, 690 m, 674 w, 659 w.
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