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Structure of 3250-74-6 * Storage: {[proInfo.prStorage]}
* 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.
General procedure: A screw capped vial was charged with nitrile (2 mmol), NaN3(2.4 mmol, 1.2 equiv.) and tetrabutylammonium bromide (2.4 mmol,1.2 equiv.). The resulting mixture was stirred at 105 °C and monitoredby TLC. After completion of the reaction, the reaction mixture wascooled to room temperature and dissolved with water (5 mL). Then, theaqueous solution was acidified with 1M HCl to pH = 3. If a precipitatewas formed, the suspension was filtered and the filter cake was washedwith water to afford the pure product. Otherwise, the aqueous solutionwas extracted with EtOAc (3 × 4 mL). The organic phase was washedwith 1M HCl (3 × 4 mL), dried with anhydrous Na2SO4, filtered andevaporated under vacuum to afford the pure product.
94%
With sodium azide; Acetate de N,N-dimethylamino-4 pyridinium In neat (no solvent) at 100℃; for 1 h;
To a round-bottomed flask containing 4-(N,N-dimethylamino)pyridiniumacetate (0.15 mmol, 0.02 g) at 100 C, 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.06 g) were added and the mixture was stirred. After1 h, the reaction was complete. The mixture was cooled and washed with coldEtOH (2 5 mL), each time it was permitted to stir for 1 h. Filtration followed bydrying of the precipitate gave the corresponding pure tetrazole as a white solid.Yield (0.14 g, 94percent); mp 242–244 C; 1H NMR (400 MHz, DMSO-d6) d (ppm): 9.10(s, 1H), 8.42 (d, J = 7.9 Hz, 1H), 8.22 (d, J = 7.9 Hz, 1H), 7.38 (t, J = 8.0 Hz, 1H); 13CNMR (100 MHz, DMSO-d6) d (ppm): 162.7, 151.9, 149.8, 137.1, 126.4, 125.3; IR(KBr) v (cm1): 3389, 2129, 2036, 1644, 1423, 1144, 1014, 754, 639, 410.
92%
With sodium azide In N,N-dimethyl-formamide at 110℃; for 5 h;
General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol), Cu complex catalyst (0.4 molpercent) and DMF (3 mL) was taken in a round-bottomed flask and stirred at 110 °C temperature. After completion of the reaction the catalyst was separated from the reaction mixture with an external magnet and reaction mixture was treated with ethyl acetate (2 × 20 mL) and 1 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2 × 15 mL). The combined organic layers were washed with water, concentrated, and the crude material was chromatographed on silica gel (Hexane-EtoAc, 1:1) to afford the pure product.
92%
With sodium azide; silver(I) triflimide In toluene at 85℃; for 2 h;
General procedure: A mixture of the appropriate nitrile (1 mmol), NaN3 (1.5 mmol),toluene (2 mL) and AgNTf2 (5 molpercent) was placed in a round bottomed flask and heated at 85 oC. The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was cooled and treated with ethyl acetate (15 mL) and 1M HCl (15 mL)and stirred vigorously. The resultant organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 × 10 mL). The combined organic layer was washed with water and concentrated to give the pure tetrazole. All the products are known compounds and the spectral data and melting points were identical to those reported in the literature. The disappearance of one strong and sharp absorption band (CN stretching band), and the appearance of an NH stretching band in the IR spectra, were characteristic of the formation of 5-substituted 1H-tetrazoles.
92%
at 100℃; for 1.3 h;
In a roundbottom flask in 100°C, consecutively, the catalyst (0.015mmol, 0.004 g), 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.065 g) were added and the mixturewas stirred for 90 min until it was completed. Then, thereaction mixture was cooled to room temperature andwashed with ethanol (25 mL). After filtration, the white In a roundbottom flask in 100°C, consecutively, the catalyst (0.015mmol, 0.004 g), 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.065 g) were added and the mixturewas stirred for 90 min until it was completed. Then, thereaction mixture was cooled to room temperature andwashed with ethanol (25 mL). After filtration, the white
90%
With sodium azide In N,N-dimethyl-formamide at 120℃; for 6 h;
General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol) and catalyst (0.02 g, contains 0.4 molpercent of Cu(II)) in DMF (3 mL) was taken in a round-bottomed flask and stirred at 120 °C. The progress of the reaction was followed by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (3×20 mL). The catalyst was removed by using magnetic field or filtration and then the resulting solution was washed with 1N HCl, dried over anhydrous Na2SO4 and then was evaporated. The crude products were obtained in excellent yields. All products were characterized by 1H, 13C NMR, FT-IR, and melting point which were in agreement with literature. We have reported the spectral data of some aromatic and heteroaromatic synthesized compounds
81%
With lithium tetraazidoborate; ammonium acetate In methanol; N,N-dimethyl-formamide at 110℃; for 8 h;
General procedure: NH4OAc (15 mg) was added to a mixture of benzonitrile(103 mg, 1 mmol) and LiB(N3)4(93 mg, 0.5 mmol) in DMF/MeOH (9/1) solution (5 mL) and stirred the mixture was at 100 oC for 8 h. After completion of reaction (monitored by TLC),the mixture was cooled to room temperature and diluted with ethyl acetate. The resulting solution was washed with 1 M HCl, dried over anhydrous Na2SO4, and concentrated. An aqueous solution of NaOH (1 M) was added to the residue, and the mixture was stirred for 30 min at room temperature. The resulting solution was washed with ethyl acetate, and then 2 M HCl was added until the pH value of the water layer became 1~2. The aqueous layer was extracted with ethyl acetate three times, and the combined organic layers were washed with 1M HCl.The organic layer was dried over anhydrous Na2SO4 and concentrated to furnish pure 5-phenyl-1-H-tetrazole 1b as a white solid (125 mg) in 86percent yield.
66%
With sodium azide; ammonium chloride In N,N-dimethyl-formamide for 24 h; Reflux
General procedure: In a typical procedure, 5-aryl-1H-tetrazoles (1–24) were synthesized by adding aryl nitriles (1 eq.), sodium azide (1.2 eq.), and ammonium chloride (1 eq.) in solvent, the mixture was refluxed for 24 h. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, 2.5 mL of 2M NaOH was added and the solution was stirred for half an hour. The reaction mixture was concentrated on reduced pressure, and dissolved in water. 3M HCl was added to the reaction mixture until precipitates formed. The precipitates were filtered and washed with distilled water. The yields of title compounds were found to be moderate to high.
46%
Stage #1: With sodium azide; ammonium chloride In DMF (N,N-dimethyl-formamide) at 90℃; for 15 h; Stage #2: With hydrogenchloride In water
[0342] 3-(1H-tetrazol-5-yl)pyridine (64). To a solution of 3-cyanopyridine (1. 1 g, 10.6 mmol) in DMF (15 mL) was added ammonium chloride (718 mg, 13.4 mmol) and sodium azide (824 mg, 12.7 mmol) and the resultant slurry was vigorously stirred at 90 °C for 15 h. The DMF was removed in vacuo, the residue was dissolved in aqueous potassium hydroxide (1 M, 20 mL), washed with EtOAc (2 x 25 mL), the aqueous layer was adjusted to pH No. 3 with aqueous HCl (6 N) and the solid was collected by filtration to afford the title compound 64 (904 mg, 46 percent yield) as a white solid: mp = 239-241 °C dec. ; 1H NMR (CDC13) b 9.21 (m, 1H), 8.76 (m, 1H), 8.39 (m, 1H), 7.64 (m, 1H) ; LRMS (ESI) m/z calcd for C6H6N5 [M + H] + 148, found 148; HRMS (ESI) m/z calcd for C6H6Ns [M + H] + 148.0623, found 148.0624 ; HPLC > 99percent (tR = 4. 88 min, 60 (A): 40 (B): 0.009 (C); tR = 3.74 min, 60 (A): 40 (B): 0.02 (C) ).
Reference：
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[2] Polyhedron, 2011, vol. 30, # 15, p. 2606 - 2610
[3] Mendeleev Communications, 2011, vol. 21, # 6, p. 334 - 336
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 2, p. 436 - 441
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[6] Applied Organometallic Chemistry, 2015, vol. 29, # 11, p. 730 - 735
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[10] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 18 - 29
[11] Journal of Chemical Research, 2015, vol. 39, # 6, p. 321 - 323
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[14] Journal of Organometallic Chemistry, 2013, vol. 743, p. 87 - 96
[15] Journal of Organic Chemistry, 2004, vol. 69, # 8, p. 2896 - 2898
[16] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4435 - 4438
[17] Tetrahedron Letters, 2013, vol. 54, # 49, p. 6779 - 6781
[18] Heteroatom Chemistry, 2011, vol. 22, # 2, p. 168 - 173
[19] Synthetic Communications, 2010, vol. 40, # 17, p. 2624 - 2632
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[31] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 224 - 239
[32] Patent: WO2005/66162, 2005, A1, . Location in patent: Page/Page column 113
[33] Patent: WO2006/86229, 2006, A1, . Location in patent: Page/Page column 25
[34] Inorganica Chimica Acta, 2014, # PA, p. 87 - 94
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2
[ 1193-92-6 ]
[ 3250-74-6 ]
Yield
Reaction Conditions
Operation in experiment
89%
With indium(III) chloride; sodium azide In N,N-dimethyl-formamide at 120℃; for 14 h;
General procedure: InCl3 (3 molpercent) was added to a stirred solution of the appropriate aldoxime (1 mmol) and NaN3 (1.5 mmol) in DMF (5 mL), and the mixture was heated to 120 °C. When the reaction was complete(TLC), the mixture was cooled to r.t., H2O (5 mL), 2 M aq HCl (10mL), and EtOAc (10 mL) were successively added, and the mixture was stirred vigorously for 15 min. The organic layer was separated, and the aqueous layer was extracted with EtOAc(3 × 15 mL). The combined organic extracts were washed with H2O, dried (Na2SO4), and filtered. The solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography [silica gel, EtOAc–hexane (9:1)].
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25 - 80℃;
Step-1: To a mixture of 3-cyanopyridine (12 g, 115 mmol) and trimethylsilyl azide (20 ml, 150 mmol), was added a solution of 0.1 M tetra-n-butylammonium fluoride in THF (57 ml, 56 mmol) at 25-30° C. temperature. The resulting mixture was heated at 80° C. for overnight. The mixture is allowed to warm at 25-30° C. temperature and then quenched in ice-water mixture. Solid precipitated out was filtered and washed with water (2.x.25 ml) and dried under vacuum to provide step-1 compound in 62percent (10.5 g) yield. MS: 148 (M+1).
With sodium azide; tetrabutylammomium bromide; at 105℃; for 12h;Sealed tube; Green chemistry;
General procedure: A screw capped vial was charged with nitrile (2 mmol), NaN3(2.4 mmol, 1.2 equiv.) and tetrabutylammonium bromide (2.4 mmol,1.2 equiv.). The resulting mixture was stirred at 105 C and monitoredby TLC. After completion of the reaction, the reaction mixture wascooled to room temperature and dissolved with water (5 mL). Then, theaqueous solution was acidified with 1M HCl to pH = 3. If a precipitatewas formed, the suspension was filtered and the filter cake was washedwith water to afford the pure product. Otherwise, the aqueous solutionwas extracted with EtOAc (3 × 4 mL). The organic phase was washedwith 1M HCl (3 × 4 mL), dried with anhydrous Na2SO4, filtered andevaporated under vacuum to afford the pure product.
94%
With sodium azide; Acetate de N,N-dimethylamino-4 pyridinium; In neat (no solvent); at 100℃; for 1h;
To a round-bottomed flask containing 4-(N,N-dimethylamino)pyridiniumacetate (0.15 mmol, 0.02 g) at 100 C, 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.06 g) were added and the mixture was stirred. After1 h, the reaction was complete. The mixture was cooled and washed with coldEtOH (2 5 mL), each time it was permitted to stir for 1 h. Filtration followed bydrying of the precipitate gave the corresponding pure tetrazole as a white solid.Yield (0.14 g, 94%); mp 242-244 C; 1H NMR (400 MHz, DMSO-d6) d (ppm): 9.10(s, 1H), 8.42 (d, J = 7.9 Hz, 1H), 8.22 (d, J = 7.9 Hz, 1H), 7.38 (t, J = 8.0 Hz, 1H); 13CNMR (100 MHz, DMSO-d6) d (ppm): 162.7, 151.9, 149.8, 137.1, 126.4, 125.3; IR(KBr) v (cm1): 3389, 2129, 2036, 1644, 1423, 1144, 1014, 754, 639, 410.
92%
With sodium azide; In N,N-dimethyl-formamide; at 110℃; for 5h;
General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol), Cu complex catalyst (0.4 mol%) and DMF (3 mL) was taken in a round-bottomed flask and stirred at 110 C temperature. After completion of the reaction the catalyst was separated from the reaction mixture with an external magnet and reaction mixture was treated with ethyl acetate (2 × 20 mL) and 1 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2 × 15 mL). The combined organic layers were washed with water, concentrated, and the crude material was chromatographed on silica gel (Hexane-EtoAc, 1:1) to afford the pure product.
92%
With sodium azide; silver(I) triflimide; In toluene; at 85℃; for 2h;
General procedure: A mixture of the appropriate nitrile (1 mmol), NaN3 (1.5 mmol),toluene (2 mL) and AgNTf2 (5 mol%) was placed in a round bottomed flask and heated at 85 oC. The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was cooled and treated with ethyl acetate (15 mL) and 1M HCl (15 mL)and stirred vigorously. The resultant organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 × 10 mL). The combined organic layer was washed with water and concentrated to give the pure tetrazole. All the products are known compounds and the spectral data and melting points were identical to those reported in the literature. The disappearance of one strong and sharp absorption band (CN stretching band), and the appearance of an NH stretching band in the IR spectra, were characteristic of the formation of 5-substituted 1H-tetrazoles.
92%
With sodium azide; piperazinium dihydrogen sulfate; at 100℃; for 1.3h;
In a roundbottom flask in 100C, consecutively, the catalyst (0.015mmol, 0.004 g), 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.065 g) were added and the mixturewas stirred for 90 min until it was completed. Then, thereaction mixture was cooled to room temperature andwashed with ethanol (25 mL). After filtration, the white In a roundbottom flask in 100C, consecutively, the catalyst (0.015mmol, 0.004 g), 3-cyanopyridine (1.0 mmol, 0.104 g) andsodium azide (1.0 mmol, 0.065 g) were added and the mixturewas stirred for 90 min until it was completed. Then, thereaction mixture was cooled to room temperature andwashed with ethanol (25 mL). After filtration, the white
90%
With sodium azide; In N,N-dimethyl-formamide; at 120℃; for 6h;
General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol) and catalyst (0.02 g, contains 0.4 mol% of Cu(II)) in DMF (3 mL) was taken in a round-bottomed flask and stirred at 120 C. The progress of the reaction was followed by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (3×20 mL). The catalyst was removed by using magnetic field or filtration and then the resulting solution was washed with 1N HCl, dried over anhydrous Na2SO4 and then was evaporated. The crude products were obtained in excellent yields. All products were characterized by 1H, 13C NMR, FT-IR, and melting point which were in agreement with literature. We have reported the spectral data of some aromatic and heteroaromatic synthesized compounds
81%
With lithium tetraazidoborate; ammonium acetate; In methanol; N,N-dimethyl-formamide; at 110℃; for 8h;
General procedure: NH4OAc (15 mg) was added to a mixture of benzonitrile(103 mg, 1 mmol) and LiB(N3)4(93 mg, 0.5 mmol) in DMF/MeOH (9/1) solution (5 mL) and stirred the mixture was at 100 oC for 8 h. After completion of reaction (monitored by TLC),the mixture was cooled to room temperature and diluted with ethyl acetate. The resulting solution was washed with 1 M HCl, dried over anhydrous Na2SO4, and concentrated. An aqueous solution of NaOH (1 M) was added to the residue, and the mixture was stirred for 30 min at room temperature. The resulting solution was washed with ethyl acetate, and then 2 M HCl was added until the pH value of the water layer became 1~2. The aqueous layer was extracted with ethyl acetate three times, and the combined organic layers were washed with 1M HCl.The organic layer was dried over anhydrous Na2SO4 and concentrated to furnish pure 5-phenyl-1-H-tetrazole 1b as a white solid (125 mg) in 86% yield.
66%
With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; for 24h;Reflux;
General procedure: In a typical procedure, 5-aryl-1H-tetrazoles (1-24) were synthesized by adding aryl nitriles (1 eq.), sodium azide (1.2 eq.), and ammonium chloride (1 eq.) in solvent, the mixture was refluxed for 24 h. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, 2.5 mL of 2M NaOH was added and the solution was stirred for half an hour. The reaction mixture was concentrated on reduced pressure, and dissolved in water. 3M HCl was added to the reaction mixture until precipitates formed. The precipitates were filtered and washed with distilled water. The yields of title compounds were found to be moderate to high.
46%
[0342] 3-(1H-tetrazol-5-yl)pyridine (64). To a solution of 3-cyanopyridine (1. 1 g, 10.6 mmol) in DMF (15 mL) was added ammonium chloride (718 mg, 13.4 mmol) and sodium azide (824 mg, 12.7 mmol) and the resultant slurry was vigorously stirred at 90 C for 15 h. The DMF was removed in vacuo, the residue was dissolved in aqueous potassium hydroxide (1 M, 20 mL), washed with EtOAc (2 x 25 mL), the aqueous layer was adjusted to pH No. 3 with aqueous HCl (6 N) and the solid was collected by filtration to afford the title compound 64 (904 mg, 46 % yield) as a white solid: mp = 239-241 C dec. ; 1H NMR (CDC13) b 9.21 (m, 1H), 8.76 (m, 1H), 8.39 (m, 1H), 7.64 (m, 1H) ; LRMS (ESI) m/z calcd for C6H6N5 [M + H] + 148, found 148; HRMS (ESI) m/z calcd for C6H6Ns [M + H] + 148.0623, found 148.0624 ; HPLC > 99% (tR = 4. 88 min, 60 (A): 40 (B): 0.009 (C); tR = 3.74 min, 60 (A): 40 (B): 0.02 (C) ).
With sodium azide; ammonium chloride; lithium chloride; In N,N-dimethyl-formamide; for 24h;Heating / reflux;
3-Cyanopyridine (1.0 g, 9.61 mmol), sodium azide (0.843 g, 12 mmol), ammonium chloride (0.694 g, 12 mmol), and lithium chloride (10 mg) were combined in DMF (10 mL) and heated at reflux behind a blast shield for 24 hours. The mixture was allowed to cool to ambient temperature, diluted with EtOAc, and washed with water. The title compound was recrystallized from EtOAc/hexanes. MS (DC]TNH3) m/z 148 (M+H)+; 1H NMR (DMSO-d6) delta 9.22 (d, IH, J=I .7 Hz), 8.77 (dd, IH, J=4.7, 1.7 Hz), 8.40 (dt, IH J=8.5, 2.0 Hz), 7.65 (ddd, IH, J=7.8, 4.8, 1.0 Hz).
With sodium azide; triethylamine hydrochloride; In toluene;
Synthesis and Characterization of Htzpya and Hpytza 5-(3-Pyridyl) tetrazole was prepared by [23] cycloadditionreactions by treating 3-cyanopyridine with NaN3 in toluene inthe presence of triethylammonium chloride.At 708C, the reaction of 5-(3-pyridyl) tetrazole with chloroacetic acid in methanolic potassium hydroxide solution gavemostly N(pyridine) products 3-(5-tetrazolyl)pyridine-1-acetatopotassium salt The reaction of 5-(3-pyridyl) tetrazole with ethylbromoacetate in methanolic potassium hydroxide solution gavemostly H(tetrazole)-substituted products 5-(3-pyridyl)tetrazole-2-acetato potassium salt.[8] Then, the pH of the solution wasadjusted to 2 with HCl (12 M). After cooling to room temperature, the precipitate was filtered off, washed with methanol(2 30 mL) and dried, forming the corresponding acid products(Htzpya or Hpytza). Htzpya: a 80 % yield was obtained based onHpytz consumed. nmax (KBr)/cm1 3426 (s), 1730 (s), 1570 (s),1420 (s), 1396 (m), 1257 (m), 1209 (m), 1146 (w), 1064 (m),1018 (w), 905 (w), 868 (w), 766 (w). Anal. Calc. for C8H7O2N5:C 46.83, H 3.44, N 34.13. Found: C 46.70, H 3.50, N 34.25 %.Hpytza: a 82 % yield was obtained based on Hpytz consumed.nmax (KBr)/cm1 3261 (s), 3102 (s), 1731 (w), 1544 (m), 1512(w), 1486 (w), 1457 (m), 1289 (m), 1229 (m), 1176 (w), 1094(w), 958 (w), 790 (w). Anal. Calc. for C8H7O2N5: C 46.83, H3.44, N 34.13. Found: C 46.75, H 3.40, N 34.18 %.
With sodium azide; In N,N-dimethyl-formamide; at 120℃; for 12h;Inert atmosphere; Green chemistry;Catalytic behavior;
General procedure: A mixture of aryl halide (1.0 mmol), K4[Fe(CN)6](0.22 mmol), 0.05 g [PS-ttet-Pd(II)], and sodium carbonate(1.0 mmol) was stirred in 5 cm3 DMF at 120 C for 1 h under an argon atmosphere. To the aryl nitrile compound generated in situ was added sodium azide (1.5 mmol) and the mixture was stirred at 120 C for appropriate time. After completion of the reaction (as indicated by TLC), the catalyst was centrifuged, washed with EtOH and the residue was diluted with 35 cm3 ethyl acetate and 20 cm3 HCl(4 N) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was extracted with 25 cm3 ethyl acetate. The combined organic layer was washed with 8 cm3 water and concentrated to give a crude product. Column chromatography using silica gel gave thepure product. All products were characterized by 1H NMR and melting point which were in agreement with literature
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 - 80℃;
Step-1: To a mixture of 3-cyanopyridine (12 g, 115 mmol) and trimethylsilyl azide (20 ml, 150 mmol), was added a solution of 0.1 M tetra-n-butylammonium fluoride in THF (57 ml, 56 mmol) at 25-30 C. temperature. The resulting mixture was heated at 80 C. for overnight. The mixture is allowed to warm at 25-30 C. temperature and then quenched in ice-water mixture. Solid precipitated out was filtered and washed with water (2×25 ml) and dried under vacuum to provide step-1 compound in 62% (10.5 g) yield. MS: 148 (M+1).
To a mixture of 3-cyanopyridine (12 g, 115 mmol) and trimethylsilyl azide (20 ml, 150 mmol), was added a solution of 0.1 M tetra-«-butylammonium fluoride in THF (57 ml, 56 mmol) at 25-30 C temperature . The resulting mixture was heated at 80 C for overnight. The mixture is allowed to warm at 25-30 C temperature and then quenched in ice-water mixture. Solid precipitated out was filtered and washed with water (2 x 25 ml) and dried under vacuum to provide step-1 compound in 62% (10.5 g) yield. MS: 148 (M+l).
To the stirred solution of 3-(lH-tetrazol-5-yl)-pyridine (10.5 g , 71.42 mmol) in toluene (50 ml) was added chloroacetic anhydride (25 g, 92.80 mmol) and resulting mixture was heated at 100 C for 2-3 hours. The reaction mixture was allowed to warm at 25-30 C temperature. The mixture was quenched with saturated aqueous sodium bicarbonate solution (500 ml) and extracted with chloroform (2 x 200 ml). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to provide a crude mass. The crude mass was purified over silica gel column chromatography to provide title compound in 56% (7.8 g) yield. MS: 196 (M+l).
With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 14h;
Example 28; Compound of Formula VII, Wherein R1 and R2 Taken Together with the Carbon Atom to which they are Attached are CCH2, and R20=(5-pyridin-3-yl-2H-tetrazol-2-ylbutyl), Rx=Ac Step 28a.; To a solution of commercially available 3-(1H-tetrazol-5-yl)-pyridine and 2-(4-Bromo-butyl)-isoindole-1,3-dione (1.0 eq.) in DMF was added Cs2CO3 at 50 C. The mixture was allowed to stirred at 50 C. for 14 hours before it was cooled back to room temperature and quenched with water and then extracted with EtOAc. The combined organic extracts were washed 2 times with water, once with brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by crystallization with EtOAc to give the desired product. MS (ESI): m/z 349.04 [M+H].
EXAMPLE 12 5-(1-Methyl-3-pyridylium)-tetrazole iodide (15) A solution of 11 (47.0 g, 0.32 mol) in N,N-dimethylformamide (250 ml) was treated with methyl iodide (90 g, 0.63 mol) at 40 C. for 2 hours. The reaction mixture was then evaporated at 60 C./1 torr, until the residue formed a thick oil. The product was crystallized from ethanol (100 ml) to yield 15 (75.3 g, 0.26 mol, 82%), M.P. 150-155 C.
(S)-N-{3-[4-(4-(5-(3-pyridinyl)-tetrazol-2-yl)-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
49%
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 14h;
To a solution of (S)-N-{3-[4-(4-methanesulfonyloxy-2-yl-piperidin-l-yl)-3-fluorophenyl ]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.37 mmol) in DMF (10 ml ) were added 5- pyridin-3-yl-lH-tetrazole (3.01 mmol) & K2CO3 (2.05mmol) and the mixture heated at 800C for 14 hour . The reaction mixture was poured in to crushed ice and the separated solid was purified by silica gel column chromatography to obtain the product in 49% yield M.P. 184-186C and MS (M+ 1) =481(MH+, 100%) for M.F. = C23H25FN8O3
(S)-N-{3-[4-(4-(5-(3-pyridinyl)-tetrazol-2-yl)-piperidin-1-yl)-3,5-difluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
49%
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 14h;
To a solution of (S)-N-{3-[4-(4-methanesulfonyloxy-2-yl-piperidin-l-yl)-3-fluoro phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.37 mmol) in DMF (10 ml ) were added 5-pyridin-3-yl-lH-tetrazole (3.01 mmol) & K2CO3 (2.05mmol) and the mixture heated at 800C for 14 hour . The reaction mixture was poured in to crushed ice and the separated solid was purified by silica gel column chromatography to obtain the product in 49% yield. M.P. 214-217C and MS (M+l) = 499(MH+, 100%) for M.F. = C23H24F^N8O3.
With diethylaluminium azide In xylene at 0 - 20℃; for 3h;
72%
Stage #1: pyridine-3-carbonitrile With sodium azide In N,N-dimethyl-formamide at 110℃; for 12h;
Stage #2: With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide
With ammonium chloride In water; N,N-dimethyl-formamide
S.7 Synthesis of 3-(2H-tetrazol-5-yl)pyridine
Synthesis Example 7 Synthesis of 3-(2H-tetrazol-5-yl)pyridine 30 g (288 mmol) of 3-pyridinecarbonitrile, 28.1 g (432 mmol) of sodium azide (NaN3), and 23.1 g (432 mmol) of ammonium chloride were dissolved in 200 mL of DMF. The solution was reacted at 100° C. for 24 hours. Then, water was added to the acquired reactant. The resulting product was neutralized with hydrochloric acid and then filtered, obtaining 19.6 g (Y=46%) of a white solid.
With sodium azide; triethylamine hydrochloride In toluene
With sodium azide; ammonium chloride In water; N,N-dimethyl-formamide
S.7 Synthesis Example 7:
Synthesis Example 7: Synthesis of 3-(2H-tetrazol-5-yl)pyridine 30 g (288 mmol) of 3-pyridinecarbonitrile, 28.1 g (432 mmol) of sodium azide (NaN3), and 23.1 g (432 mmol) of ammonium chloride were dissolved in 200 mL of DMF. The solution was reacted at 100°C for 24 hours. Then, water was added to the obtained reactant. The resulting product was neutralized with hydrochloric acid and then fitered, obtaining 19.6 g (Y=46 %) of a white solid.
With sodium azide; triethylamine hydrochloride In toluene
99 %Chromat.
With sodium azide; benzylamine hydrochloride; benzylamine In tetrahydrofuran; water at 65℃; for 24h; Inert atmosphere;
With sodium azide; zinc(II) chloride In water Reflux;
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 170℃; for 72h; Autoclave;
1; 2; 3 Example 1 Preparation of [C43H36Cu2IN40P2]n
Under normal temperature and pressure, 10 mmol of 3-cyanopyridine, 15 mmol of sodium azide and 11 mmol of ammonium chloride were weighed into an autoclave, dissolved in 15 mL of dimethylformamide, and stirred uniformly. Place it in an oven at 170 °C, remove it after three days, cool to room temperature, and pour it into a 250 mL beaker.Adjust pH=2 with concentrated hydrochloric acid, a white solid appeared.Filtration, the filter cake is the ligand 5-(3-pyridyl)-2H-tetrazole;
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 170℃; for 72h; Autoclave;
1; 2; 3 Example 1 Preparation of [C12H8Cu2N10]n
Under normal temperature and pressure, weigh 10mmol 3-cyanopyridine,15 mmol of sodium azide and 11 mmol of ammonium chloride were put into the autoclave.After dissolving in 15 mL of dimethylformamide, the mixture was stirred well, placed in an oven at 170 ° C for heat preservation, taken out after three days, cooled to room temperature, and poured into a 250 mL beaker.Adjust pH=2 with concentrated hydrochloric acid, a white solid appeared, and filtered.The filter cake is the ligand 5-(3-pyridyl)-2H-tetrazole.Weigh 0.1 mmol of 5-(3-pyridyl)-2H-tetrazole ligand and 0.15 mmol of cuprous iodidePyrex tube, followed by 0.5 mL absolute ethanol, 0.5 mL dimethylformamide, 0.5 mL acetonitrile and 0.5 mL ammonia water.After thoroughly shaking and mixing, the obtained Pyrex tube was frozen in liquid nitrogen for 5 minutes.Vacuuming (vacuum degree is 1333Pa),Sealed with a high temperature flame and placed in an oven at 65 ° C for three days.Crystal formation in the Pyrex tube,That is, the green fluorescent copper (I) complex [C12H8Cu2N10]n was obtained.
3-(5-chloromethyl-1,3,4-oxadiazole-2-yl)-pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
56%
In toluene; at 100℃;
Step-2: To the stirred solution of 3-(1H-tetrazol-5-yl)-pyridine (10.5 g, 71.42 mmol) in toluene (50 ml) was added chloroacetic anhydride (25 g, 92.80 mmol) and resulting mixture was heated at 100 C. for 2-3 hours. The reaction mixture was allowed to warm at 25-30 C. temperature. The mixture was quenched with saturated aqueous sodium bicarbonate solution (500 ml) and extracted with chloroform (2×200 ml). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to provide a crude mass. The crude mass was purified over silica gel column chromatography to provide title compound in 56% (7.8 g) yield. MS: 196 (M+1).
cis-[Ni{5-(3-pyridyl)-tetrazolato}2(phen)2][ No CAS ]
[ 3250-74-6 ]
cis-[Ni(N3)2(1,10-phen)2][ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In water; N,N-dimethyl-formamide;
General procedure: Following method has been adopted for the release of the pure tetrazoles from the corresponding nickel-tetrazolato complexes. In a typical example 0.085 g (0.1 mmol) of complex 3a was taken in 5 mL of DMF and about 0.026 g (0.4 mmol) of NaN3 dissolved in 1 mL of water was added into it with constant stirring. It gives an instantaneous green precipitate of [Ni(N3)2(phen)2]. The solution along with the precipitate was stirred for about 5 min and filtered. The filtrate was evaporated almost to dryness under reduced pressure. The solid obtained was washed several times with ethyl acetate and the washing was concentrated to obtain a colorless solid which was identified as 5-phenyl-1-H-tetrazole. Different tetrazoles were isolated in moderate to good yields (40-60%) and characterized by 1H, 13C and ESI mass spectroscopy furnishing similar data reported elsewhere [26-36]. All the tetrazoles were identified in their molecular protonated form [MH]+ in ESI-MS spectra. However, we were unable to isolate 2-Cyano-3-(1H-tetrazol-5-yl)-but-2-enedinitrile from complex 5, which was attempted in a similar method.
A mixture of nickel sulfate heptahydrate (192mg, 0.684mmol), 3-pyridyltetrazole (50mg, 0.342mmol), 300muL HF (8.7mmol) and H2O (10.00g, 556mmol) in the mole ratio 2.00:1.00:25.4:1626 was stirred briefly before heating to 180C for 48h. Purple block crystals of 5, suitable for X-ray diffraction, were isolated in 30% yield. IR (KBr pellet, cm-1): 3402(b), 1577(s) 1482(s), 1423(m), 1257(m), 1084(m), 811(s), 720(m), 597(m). Anal. Calc. for C12H16Ni3F2N10O8S: C, 21.3; H, 2.37; N, 20.8. Found: C, 21.1; H, 2.45; N, 20.6%.
5Ni(2+)*2O4S(2-)*2HO(1-)*4C6H4N5(1-)*2.5H2O[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
20%
at 150℃; for 48h;
A mixture of nickel sulfate heptahydrate (192mg, 0.684mmol), 3-pyridyltetrazole (50mg, 0.342mmol), and H2O (10.00g, 556mmol) in the mole ratio 2.00:1.00:1626 was stirred briefly before heating to 150C for 48h. Dark blue block crystals of 6, suitable for X-ray diffraction, were isolated in 20% yield. IR (KBr pellet, cm-1): 3454(b), 1433(m), 1138(m), 1077(s), 1054(s), 1022(m), 965(m) 822(w), 703(m). Anal. Calc. for C24H23N20Ni5O12.5S2: C, 25.1; H, 2.00; N, 24.4. Found: C, 25.0; H, 1.87; N, 24.4%.
A mixture of cobalt sulfate heptahydrate (193mg, 0.684mmol), 3-pyridyltetrazole (50mg, 0.342mmol), 400muL HF (11.6mmol) and H2O (10.00g, 556mmol) in the mole ratio 2.00:1.00:33.9:1626 was stirred briefly before heating to 180C for 48h. Purple block crystals of 4, suitable for X-ray diffraction, were isolated in 30% yield. IR (KBr pellet, cm-1): 3401(b), 1623(s) 1510(s), 1472(m), 1199(m), 1104(m), 834(s), 742(m). Anal. Calc. for C12H16Co3F2N10O8S: C, 21.3; H, 2.37; N, 20.7. Found: C, 21.5; H, 2.30; N, 21.0%.
[Ag6(5-(3-pyridyl)-1H-tetrazole)6(PMo12O40)2]·2H2O[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
45%
With nitric acid; at 165℃;pH 1.1;Autoclave;
General procedure: A mixture of MoO3 (0.8 mmol), AgNO3 (0.3 mmol), 3-Hpttz (0.2 mmol), KH2PO4 (0.1 mmol) was dissolved in 8.0 mL of HNO3 aqueous solution (0.25 M) and stirred for half an hour at the pH value of 2.3. Then the mixture was sealed in an 18 ml Teflon-lined reactor and heated at 165 C for 3 days. Yellow columnar crystals of compound 1 were obtained, filtered, washed with water and dried at room temperature (yield: ?50% based on Mo).
A mixture of MoO3 (0.8 mmol), AgNO3 (0.3 mmol), 3-Hpttz (0.2 mmol), KH2PO4 (0.1 mmol) was dissolved in 8.0 mL of HNO3 aqueous solution (0.25 M) and stirred for half an hour at the pH value of 2.3. Then the mixture was sealed in an 18 ml Teflon-lined reactor and heated at 165 C for 3 days. Yellow columnar crystals of compound 1 were obtained, filtered, washed with water and dried at room temperature (yield: ?50% based on Mo). Anal. Calc. for C24H18Ag7Mo12N20O41P: C, 9.06; H, 0.57; N, 8.81. Found: C, 8.89; H, 0.66; N, 8.96%. IR (solid KBr pellet, v/cm-1): 3443(m), 1608(m), 1454(m), 1424(m), 1386(m), 1061(vs), 956(vs), 875(vs), 795(vs), 674(s), 499(s).
[Ag6(5-(3-pyridyl)-1H-tetrazole)2(3-pttz)2(SiMo12O40)(H2O)2]*2H2O[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Ca.60%
With nitric acid; at 165℃;pH 3.1;Autoclave;
General procedure: A mixture of MoO3 (0.8 mmol), AgNO3 (0.3 mmol), 3-Hpttz (0.2 mmol), KH2PO4 (0.1 mmol) was dissolved in 8.0 mL of HNO3 aqueous solution (0.25 M) and stirred for half an hour at the pH value of 2.3. Then the mixture was sealed in an 18 ml Teflon-lined reactor and heated at 165 C for 3 days. Yellow columnar crystals of compound 1 were obtained, filtered, washed with water and dried at room temperature (yield: ?50% based on Mo).
Synthesis and Characterization of Htzpya and Hpytza 5-(3-Pyridyl) tetrazole was prepared by [23] cycloadditionreactions by treating 3-cyanopyridine with NaN3 in toluene inthe presence of triethylammonium chloride.At 708C, the reaction of 5-(3-pyridyl) tetrazole with chloroacetic acid in methanolic potassium hydroxide solution gavemostly N(pyridine) products 3-(5-tetrazolyl)pyridine-1-acetatopotassium salt The reaction of 5-(3-pyridyl) tetrazole with ethylbromoacetate in methanolic potassium hydroxide solution gavemostly H(tetrazole)-substituted products 5-(3-pyridyl)tetrazole-2-acetato potassium salt.[8] Then, the pH of the solution wasadjusted to 2 with HCl (12 M). After cooling to room temperature, the precipitate was filtered off, washed with methanol(2 30 mL) and dried, forming the corresponding acid products(Htzpya or Hpytza). Htzpya: a 80 % yield was obtained based onHpytz consumed. nmax (KBr)/cm1 3426 (s), 1730 (s), 1570 (s),1420 (s), 1396 (m), 1257 (m), 1209 (m), 1146 (w), 1064 (m),1018 (w), 905 (w), 868 (w), 766 (w). Anal. Calc. for C8H7O2N5:C 46.83, H 3.44, N 34.13. Found: C 46.70, H 3.50, N 34.25 %.Hpytza: a 82 % yield was obtained based on Hpytz consumed.nmax (KBr)/cm1 3261 (s), 3102 (s), 1731 (w), 1544 (m), 1512(w), 1486 (w), 1457 (m), 1289 (m), 1229 (m), 1176 (w), 1094(w), 958 (w), 790 (w). Anal. Calc. for C8H7O2N5: C 46.83, H3.44, N 34.13. Found: C 46.75, H 3.40, N 34.18 %.
Synthesis and Characterization of Htzpya and Hpytza 5-(3-Pyridyl) tetrazole was prepared by [23] cycloadditionreactions by treating 3-cyanopyridine with NaN3 in toluene inthe presence of triethylammonium chloride.At 708C, the reaction of 5-(3-pyridyl) tetrazole with chloroacetic acid in methanolic potassium hydroxide solution gavemostly N(pyridine) products 3-(5-tetrazolyl)pyridine-1-acetatopotassium salt The reaction of 5-(3-pyridyl) tetrazole with ethylbromoacetate in methanolic potassium hydroxide solution gavemostly H(tetrazole)-substituted products 5-(3-pyridyl)tetrazole-2-acetato potassium salt.[8] Then, the pH of the solution wasadjusted to 2 with HCl (12 M). After cooling to room temperature, the precipitate was filtered off, washed with methanol(2 30 mL) and dried, forming the corresponding acid products(Htzpya or Hpytza). Htzpya: a 80 % yield was obtained based onHpytz consumed. nmax (KBr)/cm1 3426 (s), 1730 (s), 1570 (s),1420 (s), 1396 (m), 1257 (m), 1209 (m), 1146 (w), 1064 (m),1018 (w), 905 (w), 868 (w), 766 (w). Anal. Calc. for C8H7O2N5:C 46.83, H 3.44, N 34.13. Found: C 46.70, H 3.50, N 34.25 %.Hpytza: a 82 % yield was obtained based on Hpytz consumed.nmax (KBr)/cm1 3261 (s), 3102 (s), 1731 (w), 1544 (m), 1512(w), 1486 (w), 1457 (m), 1289 (m), 1229 (m), 1176 (w), 1094(w), 958 (w), 790 (w). Anal. Calc. for C8H7O2N5: C 46.83, H3.44, N 34.13. Found: C 46.75, H 3.40, N 34.18 %.
[Cd(5-(3-pyridyl)-1H-tetrazole)4(CH3O)2](H3PMo12O40)*2H2O[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
43%
at 85℃; for 48h;
Synthesis of complex 1 CdCl2 (0.03 g 0.13 mmol), 3-ptzH (0.015 g 0.10 mmol) and H3PMo12O40 (0.065 g, 0.035 mmol) were dissolved in the mixed-solvent of 4 mL deionized water and 4 mL methanol (v:v = 1:1). The mixture was put in a 10 ml glass vial and heated at 85 C for 2 days. After slow cooling to room temperature, yellow block crystals of 1 were obtained and washed with distilled water, and dried in a desiccator at room temperature to give a yield of 43% based on Cd. IR (KBr pellet, cm-1): 3477 (m), 1638 (w), 1573(w), 1059 (m), 958 (s), 877 (m), 796 (s), 743 (m), 675 (m).
2,4,6-triethyl-1,3,5-benzenetricarbonyl trichloride[ No CAS ]
[ 3250-74-6 ]
1,2,3-tris(5-(3-pyridyl))-1,3,4-oxadiazole-2,4,6-triethylbenzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
55%
With pyridine; at 130℃; for 1.5h;
To 3.80 g of 2,4,6-triethyl-1,3,5-trimesoyl chloride, 5.51 g of 5- (3-pyridyl) tetrazole and 11 mL of anhydrous pyridine were added and reacted at 130 C for 1.5 hours.After the system was cooled, 100 mL of water was added and the dark crude product was filtered off with suction and dried. The residue was purified by column chromatography (ethyl acetate) to obtain 3.2 g of a light yellow powder with a yield of 55%.
With indium(III) chloride; sodium azide; In N,N-dimethyl-formamide; at 120℃; for 14h;
General procedure: InCl3 (3 mol%) was added to a stirred solution of the appropriate aldoxime (1 mmol) and NaN3 (1.5 mmol) in DMF (5 mL), and the mixture was heated to 120 C. When the reaction was complete(TLC), the mixture was cooled to r.t., H2O (5 mL), 2 M aq HCl (10mL), and EtOAc (10 mL) were successively added, and the mixture was stirred vigorously for 15 min. The organic layer was separated, and the aqueous layer was extracted with EtOAc(3 × 15 mL). The combined organic extracts were washed with H2O, dried (Na2SO4), and filtered. The solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography [silica gel, EtOAc-hexane (9:1)].
A mixture of AgNO3 (0.08 g, 0.47 mmol), 3-ptzH (0.02 g, 0.14 mmol), phen (0.02 g, 0.11 mmol),H3PMo12O40·14H2O (0.1 g), and NH4VO3 (0.06 g, 0.51 mmol) were dissolved in 10 mL of distilled waterat room temperature. The suspension was stirred for about 1 h, and pH was then adjusted to 1.0 with1.0 mol L-1 HNO3. The suspension was transferred to a Teflon lined autoclave (25 mL) and kept at 160 Cfor 5 days. After slowly cooling to room temperature, orange block crystals of 2 were obtained (35%yield based on Mo). Elemental analysis for C36H25Ag4Mo12N14O40P: Calcd C, 14.85; H, 0.85; N, 6.74 (%).Found: C, 14.67; H, 0.87; N, 6.62 (%). IR (KBr pellet, cm-1): 3465(s), 2355(m), 1628(w), 1428(w), 1076(s),972(s), 886(m), 812(s), 516(m).
A mixture of AgNO3 (0.08 g, 0.47 mmol), 3-ptzH (0.02 g, 0.14 mmol), phen (0.02 g, 0.11 mmol),H3PMo12O40·14H2O (0.1 g), and NH4VO3 (0.06 g, 0.51 mmol) were dissolved in 10 mL of distilled waterat room temperature. The suspension was stirred for about 1 h, and pH was then adjusted to 1.0 with1.0 mol L-1 HNO3. The suspension was transferred to a Teflon lined autoclave (25 mL) and kept at 160 Cfor 5 days. After slowly cooling to room temperature, orange block crystals of 2 were obtained (35%yield based on Mo).
In water; N,N-dimethyl-formamide; at 100℃; for 120h;Sealed tube;
In order to prepare 1,4-terephthalic acid-controlled tetrazole coordination polymer as an example,The structure unit is Cd5 (L1) (L2) s (Sol) 6, where L1 is 1,4-terephthalic acid divalent anion, L2 is 5-pyridyltetrazole monovalent anion, Sol is N, N-dimethylformamide, the specific preparation method is as follows: In order to prepare 1,4-terephthalic acid-controlled tetrazole coordination polymer as an example,The structure unit is Cd5 (L1) (L2) s (Sol) 6, where L1 is 1,4-terephthalic acid divalent anion, L2 is 5-pyridyltetrazole monovalent anion, Sol is N, N-dimethylformamide, the specific preparation method is as follows:(0.20 mmol) l, 4-terephthalic acid,0 · 06 g (0.4 mmol) of 5-pyridyltetrazole,0 · 062 g (0.2 mmol) of cadmium nitrate was added to 6 mL of N, N-dimethylformamide,Stir the hook, sealed, 100 C constant temperature for 5 days, natural cooling to room temperature, prepared into 1,4-terephthalic acid controlled tetrazole coordination polymer, the yield of 60%
In acetonitrile; at 115℃; for 72h;Sealed tube; Autoclave; High pressure;
A mixture of CuSCN (0.20 mmol), 3-ptz (0.20 mmol), and acetonitrile (8 mL) was sealed in a 15-mL Teflon-lined reactor,which was heated at 115C for 72 h.. Upon cooling to roomtemperature at a rate of 10C h-1, yellow rod crystals of 1 wereobtained with 46% yield based on 3-ptz. Anal. Calc. forC7H5N6SCu (%): C, 31.28; H, 1.88; N, 31.27. Found: C, 31.82; H, 1.81; N, 33.05%. IR (KBr, cm1): 3060w, 2158 m, 2091 s,1639 m, 1610 m, 1579 s, 1459 s, 1397 m, 1226 m, 913 m, 826 s,778 m, 749 m, 710 s, 684 s.
To an ethanol/water solution(10 mL) of 1,2,3-benzenetricarboxylic acid (0.0210 g, 0.1 mmol) was added M-pyridyltetrazolium(0.0147 g, 0.1 mmol) with constant stirring for20 min. The mixed solution was sealed with a sealing film and leftto stand at room temperature, colorless transparent crystals wereformed after several days. After compound 2 was filtered and theliquid was dried by filter paper, the morphology of the crystal wasobserved under an optical microscope. At last, crystals suitable forX-ray diffraction were selected. Anal. Calcd for C15H15N5O8: C,45.76; H, 3.81; N, 17.79%. Found: C, 45.81; H, 3.75; N, 17.83%.IR(cm-1): 3505 (s), 3449 (s), 3147 (m), 2930 (m), 2851 (m), 1665 (s), 1632 (s), 1600 (s), 1476 (s). 1H NMR (500 MHz; DMSO-d6): deltaH, ppm7.54 (s, 2H, 1,2,3-benzenetricarboxylic acid-C6H3), 7.65-7.68 (dd,J= 8.0, 5.0 Hz 1H, M-pyridyltetrazolium-C5NH4), 7.95 (s, 1H, 1,2,3-benzenetricarboxylic acid-C6H3), 8.41 (d, J= 7.5 Hz, 1H, M-pyridyltetrazolium-C5NH4), 8.78 (d, J= 4.5 Hz, 1H, M-pyridyltetrazolium-C5NH4), 9.22 (s, 1H, M-pyridyltetrazolium-C5NH4).
We mixed 0.043 mmol of 10 mg Cu(NO3)2·2.5H2O,0.031 mmol and 6 mg L-1, 1 mL of H2O,and 4 mL ofdimethylformamide (DMF) to generate a mixture. Wethen placed 20 mL of the mixture into a vessel with capand heated the mixture for 7 days at 80 C. The prepared 1?s polyhedron blue crystals were harvested via filtrationand dried in air, and its yield was 52% on the basis of theL ligand. Elemental analysis showed that the calculated composition of C21H33CuN13O5was 35.29% C, 2.94% H,and 25.74% N, and its actual composition was 35.21% C,2.98% H, and 25.79% N. The selected FT-IR result forKBr pellet cm-1 is as follows: 3410 (br), 3122 (s), 3054(s), 1612 (s), 1545 (s), 1351 (s), 1205 (s), 1154 (s), 1111(s), 1055 (s), 967 (s), 876 (s), 697 (s), and 642 (s).
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