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CAS No. : | 54258-41-2 | MDL No. : | MFCD00455733 |
Formula : | C12H9N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DKPSSMOJHLISJI-UHFFFAOYSA-N |
M.W : | 195.22 | Pubchem ID : | 606970 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 14 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 61.45 |
TPSA : | 51.8 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 1.29 |
Log Po/w (XLOGP3) : | 1.78 |
Log Po/w (WLOGP) : | 2.37 |
Log Po/w (MLOGP) : | 1.25 |
Log Po/w (SILICOS-IT) : | 2.23 |
Consensus Log Po/w : | 1.78 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.86 |
Solubility : | 0.268 mg/ml ; 0.00137 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.49 |
Solubility : | 0.637 mg/ml ; 0.00327 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.65 |
Solubility : | 0.00439 mg/ml ; 0.0000225 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H312-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
72.9% | With hydrazine hydrate; palladium 10% on activated carbon In ethanol at 72℃; for 10 h; | 4) 0.64 g (6.0 mmol) of 10percent palladium on carbon was weighed as a catalyst,4.85 g 80percent (mass fraction)Hydrated hydrazineAnd 20.0 mL of absolute ethanolWas added to a 250 mL three-necked flask,The three-necked flask was mounted on a DF-101S heated thermostatic heated magnetic stirrer,In the three-necked flask on the installation of reflux condenser,And the glass plug with three plugs of the remaining two mouth.The oil bath temperature was set at 72 ° C and stirred,At this point weigh2.03 g (9 mmol) of 5-nitro-1,10-phenanthroline was charged into a three-necked flask,Then add 40 mL of absolute ethanol and allow it to dissolve completely (total ethanol)By adding the amount to completely dissolve 5-nitro-1,10-phenanthroline.When the oil bath temperature reaches the set temperature,The dissolved solution was quickly poured into a three-necked flask.After 10 hours of reaction,And then put it aside for about 10h,And then re-warming the oil bath to 60 ,When the precipitate in the reaction system is redissolved,Immediately remove the three-necked flask and pour out the solution to hot filter,The residue was rinsed with anhydrous ethanol for about 5 times.Take the filtrate and use a rotary evaporator to sprinkle the solvent,To give a yellow-brown solid,Remove the yellowish brown solid with a vacuum ovenDried at 60 ° C for 12 hours,Finally, the product was purified by recrystallization from absolute ethanol,filter,60 ° C under vacuum for 12 hours,To give 1.28 g of a yellow-brown solid powder,This powder is 5-amino-1, 10-phenanthroline (Phen-NH2)The yield was 72.9percent. |
60% | With palladium 10% on activated carbon; hydrazine hydrate In ethanol at 78℃; for 5 h; Inert atmosphere | A suspension of 5-nitro-1,10-phenanthroline (5, 4.5 g,19.98 mmol) and Pd/C (10 percent) (0.8 g), in ethanol (100 mL) was heated to 78 °C under N2 atmosphere. Hydrazine hydrate (3.0 mL, 61.5 mmol) was added, and the reaction mixture was heated under reflux for 5 h. The solution was filtered while hot and the solvent was removed under reduced pressure to give yellow solid which was recrystallized from ethanol. 2.71 g, yield: 60 percent, mp: 248–250 °C. 1H NMR (400 MHz, CDCl3, δ;ppm): 9.20 (d, J = 4.1 Hz, 1H), 8.95 (d, J = 4.1 Hz, 1H), 8.29(d, J = 8.3 Hz, 1H), 7.99 (d, J = 8.3 Hz, 1H), 7.65 (dd, J = 8.2–4.0 Hz, 1H), 7.51 (dd, J = 8.1–3.9 Hz, 1H), 6.96 (s, 1H); FTIR(cm−1): 3416, 3318, 3215, 3029, 2971, 1738, 1634, 1406,841, 739. |
47% | With palladium 10% on activated carbon; hydrazine hydrate In ethanol at 70℃; for 10 h; Inert atmosphere | Five grams (22.2 mmol) of 5-nitro-1,10-phenanthroline were dissolved in 100 ml of absolute ethanol. Ten mole per cent of Pd/C, i.e. 1 g, was added as a catalyst. The reaction assembly was purged with argon, and then 13 ml (26.7 mmol) hydrazine monohydrate was added dropwise over a period of 30 min. The mixture was stirred for 10 h at 70°C. After the completion of reaction, the mixture was hot filtered to remove the catalyst, and the filtrate was dried over Na2SO4 and concentrated by using rotary evaporator and then dried. A 2.1 g of yellow solid was obtained with 47percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | palladium-carbon; In EtOH, hydrazine hydrate; | B. Preparation of 1,10-Phenanthroline-5-amine This compound was synthesised by the reduction of 5-nitro-1,10-phenanthroline. The procedure was manipulated under argon. To a suspension of 5-nitro-1,10-phenanthroline (2.06 g, 9.0 mmol) and 10% Pd/C (0.280 g) in 90 ml of 95% EtOH, hydrazine hydrate (2.0 ml, 42 mmol) was added dropwise. The mixture was heated for 3 h at 70 C. and then filtered hot through a glass-fiber filter to remove the catalyst. The yellow solution was concentrated to 25 ml and left at 4 C. for 24 hours. The precipitate was filtered off, washed with cold Et2O, and dried under vacuum for 24 hours to give 1.425 g of product (81%). 1H-NMR (DMSO-d6): delta=9.08 (m, 1H), 8.71 (m, 2H), 8.06 (m, 1H), 7.75 (q, 1H), 7.52 (q, 1H), 6.90 (s, 1H), 6.17 ppm (d, NH2). 13C-NMR (DMSO-d6): delta=149.3, 146.2, 144.8, 142.7, 140.5, 132.7, 130.8, 123.2, 122.0, 101.8 ppm. |
72.9% | With hydrazine hydrate; palladium 10% on activated carbon; In ethanol; at 72℃; for 10h; | 4) 0.64 g (6.0 mmol) of 10% palladium on carbon was weighed as a catalyst,4.85 g 80% (mass fraction)Hydrated hydrazineAnd 20.0 mL of absolute ethanolWas added to a 250 mL three-necked flask,The three-necked flask was mounted on a DF-101S heated thermostatic heated magnetic stirrer,In the three-necked flask on the installation of reflux condenser,And the glass plug with three plugs of the remaining two mouth.The oil bath temperature was set at 72 C and stirred,At this point weigh2.03 g (9 mmol) of 5-nitro-1,10-phenanthroline was charged into a three-necked flask,Then add 40 mL of absolute ethanol and allow it to dissolve completely (total ethanol)By adding the amount to completely dissolve 5-nitro-1,10-phenanthroline.When the oil bath temperature reaches the set temperature,The dissolved solution was quickly poured into a three-necked flask.After 10 hours of reaction,And then put it aside for about 10h,And then re-warming the oil bath to 60 ,When the precipitate in the reaction system is redissolved,Immediately remove the three-necked flask and pour out the solution to hot filter,The residue was rinsed with anhydrous ethanol for about 5 times.Take the filtrate and use a rotary evaporator to sprinkle the solvent,To give a yellow-brown solid,Remove the yellowish brown solid with a vacuum ovenDried at 60 C for 12 hours,Finally, the product was purified by recrystallization from absolute ethanol,filter,60 C under vacuum for 12 hours,To give 1.28 g of a yellow-brown solid powder,This powder is 5-amino-1, 10-phenanthroline (Phen-NH2)The yield was 72.9%. |
60% | With palladium 10% on activated carbon; hydrazine hydrate; In ethanol; at 78℃; for 5h;Inert atmosphere; | A suspension of 5-nitro-1,10-phenanthroline (5, 4.5 g,19.98 mmol) and Pd/C (10 %) (0.8 g), in ethanol (100 mL) was heated to 78 C under N2 atmosphere. Hydrazine hydrate (3.0 mL, 61.5 mmol) was added, and the reaction mixture was heated under reflux for 5 h. The solution was filtered while hot and the solvent was removed under reduced pressure to give yellow solid which was recrystallized from ethanol. 2.71 g, yield: 60 %, mp: 248-250 C. 1H NMR (400 MHz, CDCl3, delta;ppm): 9.20 (d, J = 4.1 Hz, 1H), 8.95 (d, J = 4.1 Hz, 1H), 8.29(d, J = 8.3 Hz, 1H), 7.99 (d, J = 8.3 Hz, 1H), 7.65 (dd, J = 8.2-4.0 Hz, 1H), 7.51 (dd, J = 8.1-3.9 Hz, 1H), 6.96 (s, 1H); FTIR(cm-1): 3416, 3318, 3215, 3029, 2971, 1738, 1634, 1406,841, 739. |
47% | With palladium 10% on activated carbon; hydrazine hydrate; In ethanol; at 70℃; for 10h;Inert atmosphere; | Five grams (22.2 mmol) of 5-nitro-1,10-phenanthroline were dissolved in 100 ml of absolute ethanol. Ten mole per cent of Pd/C, i.e. 1 g, was added as a catalyst. The reaction assembly was purged with argon, and then 13 ml (26.7 mmol) hydrazine monohydrate was added dropwise over a period of 30 min. The mixture was stirred for 10 h at 70C. After the completion of reaction, the mixture was hot filtered to remove the catalyst, and the filtrate was dried over Na2SO4 and concentrated by using rotary evaporator and then dried. A 2.1 g of yellow solid was obtained with 47% yield. |
With ammonium sulfide; In ethanol; water; | PREPARATION 1 5-Amino-1,1 0-Phenanthroline FIG. 1A schematically illustrates the synthesis of 5-amino-1,10-phenanthroline (Science 237:1197, 1987). 5-Nitro-1,10-phenanthroline (1) (Aldrich; 2.00 g; 8.88 mmol) was dissolved in 80 ml hot absolute ethanol. The resulting solution was added dropwise under nitrogen into 95 ml of 20% ammonium sulfide. Addition took place over 1 hr., after which 40 ml of 20% ammonium sulfide was added, and reaction mixture was refluxed for an additional 1 hr. The reaction mixture then was allowed to cool to room temperature, and then was extracted three times with 500 ml chloroform. The pooled chloroform extracts were back-extracted with 300 ml deionized water, were dried over anhydrous sodium sulfate, and were evaporated under vacuum. The resulting yellow solid was dissolved in 100 ml hot absolute ethanol, and the solution was filtered. The volume of the filtrate was reduced to 50 ml by evaporation, and 50 ml deionized water was added. Crystals were harvested after 24 hr. at 4 C. and were dried under vacuum. Yield: 727 mg, 42% | |
With hydrazine;palladium on activated charcoal; In ethanol; at 40℃; for 3h; | Example 5: 5-Amino-1,10-phenanthroline; 1.0 g (4.4 mmol) of 5-nitro-1,10-phenanthroline is heated to 40C in 15 ml of absolute ethanol with 0.6 ml (12 mmol) of hydrazine hydrate (100 %). The reduction is started by adding a spatula tip of Pd/C, whereupon considerable evolution of nitrogen can immediately be observed. The reaction is maintained for a further 3 hours by the regular addition of catalyst. The mixture is then heated to reflux in order to concentrate excess hydrazine hydrate. After cooling, the catalyst is filtered off, the solvent is removed in vacuo and the crude product is dried for one hour under a water-jet vacuum. 5-Amino-1,10-phenanthroline is used for the following reaction without further purification. | |
With 5%-palladium/activated carbon; hydrazine hydrate; | The synthesis of this compound was performed by nitration of 1,10-phenanthroline in a mixture of 95% sulfuric acid and concentrated nitric acid [1], followed by reduction of the nitro derivative with hydrazine over a 5% Pd/C catalyst. The synthetic procedure has been described in detail elsewhere [2]. Mp: 253-254 C. Anal for C12H9N3 Calcd. (Found): C, 73.83 (73.78); H, 4.65 (4.70); N, 21.52 (21.54). 1H NMR (400 MHz, CDCl3): delta (ppm) = 9.11 (dd, J = 4.28, 1.46 Hz, 1H), 8.86 (dd, J = 4.27, 1.59 Hz, 1H), 8.17 (dd, J = 8.33, 1.51 Hz, 1H), 7.88 (dd, J = 8.08, 1.38 Hz, 1H), 7.54 (dd, J = 8.33, 4.30 Hz, 1H), 7.41 (dd, J = 8.09, 4.31 Hz, 1H), 6.83 (s, 1H), 4.19 (s, 2H). EIMS (70 eV) m/z: M+ 195 (100), 168 (18), 140 (14). | |
With 5%-palladium/activated carbon; hydrazine hydrate; In ethanol; at 70℃; for 5h; | 5-Amino-1,10-phenanthroline (denoted as phen-NH2) was prepared as described in Ref. [33]. 10g 24 1,10-phenanthroline was added to a three-necked flask, then added 15ml of 25 concentrated sulfuric acid, mixing, continue stirring and heating, slowly dropping a mixture of 60ml of concentrated sulfuric acid and concentrated nitric acid (VH2SO4:VHNO3=1:1), control the heated temperature does not exceed 170C, refluxed for 3h, cooled to room temperature, the reaction solution was poured into ice-water, adjust the pH to about 6.0 with a 10% 26 NaOH solution, that yellow solid precipitation, filtration, washing, drying, recrystallized from ethanol and dried to give a pale yellow solid 5-nitro-1,10-phenanthroline morpholine. 27 Hydrazine hydrate (1mL) diluted in 28 ethanol (20mL) was added dropwise to a suspension of 29 5-nitro-1,10-phenanthroline (1g) with 5% 30 Pd/C (200mg) in ethanol. The mixture was stirred at 70C for 5h. After filtration, the solution was concentrated until the formation of a green-yellow precipitate. The yellow solid was filtered off and washed with water. IR: 3470, 3416, 3250, 3059, 1643, 1618, 1587, 1562, 1504, 1493, 1446, 1420, 1384, 1344, 1217, 1141, 1092, 853, 735, 724, 709, 624cm-1 | |
With 5%-palladium/activated carbon; hydrazine hydrate; In ethanol; at 65 - 70℃; for 12h;Darkness; | In a N2 environment, 10 g of PN was dissolved in 150 mL of absolute ethanol.When 3.2 g of 5% Pd/C catalyst was added and heated to 65-70 C, 45 g of hydrazine hydrate was slowly added dropwise, and the reaction was stirred for 12 h in the dark.The Pd/C catalyst was removed by hot filtration with diatomaceous earth, and then distilled under reduced pressure to remove excess hydrazine hydrate and ethanol.A large amount of yellow precipitate appeared, which was suction filtered to give a yellow solid, which was then recrystallized from ethanol to give PNH (5-amino-1, 10-phenanthroline). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine; In dimethyl sulfoxide; for 1h;Reflux; | Part A: Synthesis of Bridging Group; Terephthaloyl chloride (Sigma-Aldrich) (0.31 g, 1.53 mmol) was dissolved in 10 mL of DMSO anhydrous, and then it was dripped into 5-amino-1,10-phenanthroline solution made up by 5-amino-1,10-phenanthroline (Polysciences) (0.60 g, 3.08 mmol) and triethylamine (0.466 g, 4.61 mmol) dissolved in 15 mL of DMSO anhydrous at 0 C. The reaction was allowed to warm to room temperature slowly and then refluxed for 1 hour to finish the reaction. The crude was washed by water (5×20 mL), dried over Na2SO4 and then yield the product under reduced pressure and high temperature. (product: 0.76 g, yield: 96% before further purification). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 6: N-(1-Hexyl-heptyl)-N'-(5-(1,10-phenanthrolin)-yl)-perylene-3,4:9,10-bis(dicarboximide); 1.72 g (3.00 mmol) of N-(1-hexyl-heptyl)-perylene-3,4:9,10-tetracarboxylic acid 3,4-anhydride 9,10-imide and 0.87 g (4.40 mmol) of unpurified 5-amino-1,10-phenanthroline are reacted for 3 hours at 150C in 10 g of imidazole with the addition of 0.10 g (0.45 mmol) of zinc acetate dihydrate. The reaction product is introduced with about 50 ml of ethanol into 300 ml of 2N hydrochloric acid and stirring is carried out for 2 hours at room temperature. The resulting precipitate is filtered off, washed with water/methanol and dried for 16 hours at 120C. The crude product can first be separated over aluminium oxide/chloroform/ethanol (10 + 1) into two rough fractions A and B. Fraction A is discarded. The main fraction B is first applied to a column of silica gel/chloroform/glacial acetic acid (10 + 1). It is thus possible to elute some of the impurities, while N-(1-hexyl-heptyl)-N'-(5-(1,10-phenanthrolin)-yl)-perylene-3,4:9,10- bis(dicarboximide) remains firmly adsorbed on the material of the column. Desorption of N-(1-hexyl-heptyl)-N'-(5-(1,10-phenanthrolin)-yl)-perylene-3,4:9,10-bis(dicarboximide) is carried out with the eluant mixture chloroform/triethylamine (10 + 1). Yield 0.65 g, m.p. > 350C. - RF (silica gel/CHCl3/triethylamine (10 + 1)) = 0.58. - IR (KBr): nu = 2955 cm-1 (m), 2928 (m), 2857 (m), 1710 (m, sh), 1698 (s), 1658 (s, br.), 1596 (s), 1579 (m), 1510 (w), 1438 (w), 1431 (w), 1405 (m), 1368 (w, sh), 1355 (m, sh), 1344 (s), 1253 (m), 1205 (w), 1176 (m), 1110 (w), 968 (w), 855 (w), 830 (w), 811 (m), 748 (m), 742 (m), 730 (w), 690 (w). - C49H42N4O4: calc. 750.3206; found 750.3208 (MS). - C49H42N4O4 (750.9): calc. C 78.38, H 5.64, N 7.46; found C 76.85, H 5.61, N 7.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.75 g (66%) | In hydrogenchloride; acetic acid | 6.2 (2) (2) Synthesis of 5-amino-1,10-phenanthroline (Compound (2)) In 3.0 ml of acetic acid was dissolved 1.37 g (5.8 mmol) of 5-nitro-1,10-phenanthroline. A solution prepared by dissolving 1.08 g (4.8 mmol) of stannic chloride (II) dihydrate in 2.2 ml of concentrated hydrochloric acid was added dropwise thereto, followed by stirring at 100° C. for 2 hours. The reaction mixture was made alkaline with a NaOH aqueous solution and extracted with chloroform. After chloroform was distilled off under reduced pressure, a yellow solid was obtained. This was recrystallized from tetrahydrofurane-hexane to obtain 0.75 g (66%) of the desired 5-amino-1,10-phenanthroline (Compound (2)). 1 H-NMR (CDCl3): δ=6.95 (s, 1H), 7.50 (m, 1H), 7.65 (m, 1H), 7.98 (d, 1H), 8.28 (d, 1H), 8.95 (d, 1H), 9.20 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.08 g (62%) | In ethanol | III. 5-Amino-1,10-phenanthroline. A magnetically stirred solution of 5nitro-1, 10-phenanthroline (2,.01 g, 8.93 mmol) and tin(II) chloride dihydrate (6.05 g, 26.81 mmol) was heated to reflux for 3 h in ethanol (100 mL) and then concentrated in vacuo to give a viscous residue. The residue was treated with concentrated NaOH and then extracted with CHCl3 (3*50 mL). The organic layer was separated, washed with water (2*50 mL) and brine (1*50 mL), dried over anhydrous sodium sulfate, and then concentrated in vacuo to afford 1.08 g (62%) of the amine as a tan solid: m.p. 255-258 C; MS(fab):m/e 196 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | General procedure: 2-(Thiophen-2-yl)quinoline was synthesized accordingto the previous report.25. The cyclometalatediridium(III) chloro-bridged dimers [Ir(ppy)2Cl]2 and[Ir(thq)2Cl]2 were prepared with 2-phenylpyridine (ppy)and 2-(thiophen-2-yl)quinoline (thq) respectively according to literature methods.26. The Ir(ppy)2(phen-NH2 and Ir(thq)2(phen-NH2) complexes were synthesized by reaction of chloro-bridged dimer [Ir(ppy)2Cl]2 and[Ir(thq)2Cl]2 with 5-amino-1,10-phenanthroline (phen-NH2) respectively (see Scheme 1). The solutions of [Ir(ppy)2Cl]2 (0.161 g, 0.15 mmol) combined with phen-NH2 (0.073 g, 0.375 mmol) and [Ir(thq)2Cl]2(0.194 g, 0.15 mmol) combined with phen-NH2 (0.073 g,0.375 mmol) in CH2Cl2-MeOH (15 mL, 2:1 v/v) were heated to reflux respectively. After 3-5 h, the red solutions were cooled to room temperature, then a 6-fold excess of potassium hexafluorophosphate was added and the mixture was further stirred for 1 h. The suspensions were filtered to remove insoluble inorganic salts. The solutions were evaporated to dryness under reduced pressure. The crude product of Ir(ppy)2(phen-NH2+PF-6 (complex 1)was chromatographed with CH2Cl2/acetone (20:1) to produce a yellow solid in a 73% yield. 1H NMR (400 MHz,CDCl3): = 691-6.94 (m, 4H), 6.97-7.05 (m, 4H),7.09 (s, 1H), 7.42-7.45 (t, 2H), 7,68-7.73 (m, 2H),7.84-7.88 (t, 2H), 7.90-7.93 (t, 2H), 8.12 (d, 1H), 8.22(d, 2H), 8.37 (d, 1H), 8.39 (d, 1H); The crude product ofIr(thq)2(phen-NH2)PF-6 (complex 2) was chromatographed with CH2Cl2/acetone (20:1) to produce a yellow solidin a 65% yield. 1H NMR (400 MHz, CDCl3: = 635(s, 2H), 6.85 (s, 1H), 6.92 (d, 2H), 7.17-7.21 (m, 4H),7.37-7.41 (t, 2H), 7.54-7.59 (m, 4H), 7.77-7.87 (m, 4H),7.98-8.07 (m, 4H), 8.31 (d, 1H), 8.71 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With bismuth (III) nitrate pentahydrate; at 20℃; for 1h;Sonication; Neat (no solvent); | General procedure: Amine 2 (1.0 mmol), 2,5-dimethoxytetrahydrofuran (1, 1.2 mmol) and bismuth nitrate pentahydrate (24 mg, 5 mol%) was irradiated in a B5510-DTH (Branson ultrasonic cleaner; Model-5510, frequency 42 kHz with an output power 135 Watts), as specified in Table 2. After completion of the reaction (monitored by TLC) diethyl ether (10 mL) was added to the reaction mixture and filtered. Pure product was isolated from the reaction mixture after evaporation of ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethanol; at 70℃; | 5-amino-1, 10-phenanthroline has been synthesized from 1,10-phenathroline using the known literature methods [28]. 5-amino-1, 10-phenanthroline (0.5g, 2.56 mmol) was dissolved in 5ml of hot absolute ethanol. To this hot stirring solution of 5-amino-1,10-phenanthroline, salicyldehyde (0.312 g, 2.56 mmol) was added and the contents were heated at 70 C till the TLC indicated completion of the reaction [29]. Yellow colored solid separated at the completion of the reaction. The yellow residue was filtered and collected as crude product. Recrystallization of crude solid from CHCl3/CH3OH resulted in the formation of pure product 1.Yellow solid, 85% Yield; M.P: 196C. Selected FT-IR peaks (cm-1): 3411 (upsilonO-H), 3060 (upsilonC-Hstr., aromatic), 1617 (upsilonC=NH) 1H NMR (DMSO, 400MHz) delta: 7.07-7.01 (m, 2H, Ar-H), 7.49 (t, J=7.08 Hz, 1H, Ar- H), 7.89-7.75 (m, 4H, Ar-H), 8.48 (d, J=7.92, 2H, Ar-H), 8.67 (d, J=7.08 Hz, 1H, Ar-H), 9.05 (s, 1H, Ar-H), 9.17 (s, 2H, Ar-H); 13C NMR (DMSO, 100 MHz) delta: 112.61, 117.45, 119.16, 119.59, 123.29, 123.49, 125.21, 128.57, 132.06, 132.82, 134.18, 135.88, 145.07, 145.38, 146.34, 149.87, 150.94, 161.25, 164.99. ESI-MS: m/z=300.14 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium hydrogencarbonate; In diethyl ether; dichloromethane; acetonitrile; | 1. Synthesis of methyl 5-(1,10-phenanthrolin-5-ylcarbamoyl)pentanoate 1,10-Phenanthrolin-5-amine (0.488 g) and sodium bicarbonate (0.252 g) were mixed in 30 mL dry acetonitrile and chilled on ice. Methyl adipoyl chloride (584 muL) dissolved in 40 mL dry acetonitrile was added slowly. The mixture was stirred on ice for 4 h. The volume was reduced under vacuum to a few mL and the material was washed with diethyl ether, collected by filtration and dissolved in 200 mL methylene chloride. The solution was filtered and the volume was reduced under vacuum to a few mL. Addition of diethyl ether precipitated the product as an orange gum, which was dried under vacuum, yielding 0.504 g of material (60% yield) which appeared pure by thin-layer chromatography (1:1 methylene chloride:methanol, silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 80℃; for 12h; | Phen-Si was synthesized by using phen-NH2 as the starting reagent [34-37]. phen-NH2 (0.212g, 1mmol) was dissolved in 20mL of CHCl3 in a flask. The solution was stirred while 2mL of TEPIC was added dropwise. The chloroform was evaporated at atmospheric pressure, and the resulting mixture was heated at 80C in a covered flask for 12h. Cold hexane was then added to precipitate the white powder. The powder was collected by filtration, purified in methanol, and dried in a vacuum. 1H NMR (CDC13, Me4Si): 0.56 (4H, m), 1.16 (18H, t), 1.62 (4H, m), 3.22 (4H, m), 3.71 (12H, q), 7.21 (2H, s), 7.68 (2H, m), 7.88 (1H, s), 8.24 (2H, m), 9.24 (2H, m). IR: CONH (1653, 1538cm-1), C-Si (1162cm-1), Si-O (1090cm-1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.6% | With sodium tetrafluoroborate; In ethanol; water; at 2 - 70℃; | 172 mg (0.87 mmol) phen.H2O, 185 mg (0.87 mmol) (5-NH2-phen).H2O, 274 mg (2.5 mmol) NaBF4 and 5 ml of 96% EtOH were dissolved in 30 ml distilled water at 70 C. Then the solution was brought to ambient temperature, and distilled H2O added to 50 ml. The solution was kept in a refrigerator at 2-3 C for 30 d. The formed yellow-brown crystals were filtered off, washed with distilled water and ethyl ether and dried in a desiccator over P4O10.Yield: 50.6%.Anal. calcd. for C36H32N8O3 (C, H, N):Calculated (%): C, 69.15; H, 5.12; N, 17.92.Found (%): C, 69.23; H, 5.19; N, 18.36.FTIR (cm-1): 625, 737, 843, 1409, 1488, 1618, 1651, 3237, 3348.CIMS(CH4): 181 [phenH+]+.Compounds 2, 3, 4 and 5 were prepared under identical conditions to 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine; In acetonitrile; at 20℃; for 24h;Inert atmosphere; | To a suspension of 5-amino-1,10-phenanthroline (0.98 g, 5.0 mmol) in 20 mL of acetonitrile was added dropwise with stirring a solution of acryloyl chloride (1.5 mL), triethylamine (2 mL), and acetonitrile (15 mL) at room temperature under an argon atmosphere. The reaction was allowed to continue for 24 h. After concentration under reduced pressure the residue chromatographed on a silica column (25 mm × 200 mm) with 9:1 chloroform/ethanol as the eluent. Removal of the solvent from the desired eluate fraction gave 0.88 g (70%) of yellow crystals. Anal for C15H11N3O Calcd. (Found): C, 72.28 (72.23); H, 4.45 (4.49); N, 16.86 (16.89). IR (KBr) numax: 3360 (NH), 1658 (CO), 1631 cm-1 (CC). 1H NMR (400 MHz, CDCl3): delta (ppm) = 8.98 (d, J = 8.25 Hz, 2H), 8.80 (s, 1H), 8.29 (d, J = 8.14 Hz, 1H), 8.03 (d, J = 8.32 Hz, 2H), 7.52 (dd, J = 7.94, 4.28 Hz, 1H), 7.40 (s, 1H), 6.51 (d, J = 5.25 Hz, 2H), 5.79 (m, 1H). 13C NMR (100 MHz, CDCl3): delta (ppm) = 165.41, 149.38, 149.24, 145.65, 143.85, 135.68, 130.94, 130.85, 130.71, 128.23, 127.81, 124.49, 123.19, 122.29, and 120.56. EIMS (70 eV) m/z: M+ 249 (57), 221 (7), 195 (100), 167 (35), 140 (19), 55 (41). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In toluene; for 1h;Reflux; Irradiation; | The synthesis of RePhenNH2 was adapted from a literaturemethod described by Bessette et al.[16] <strong>[54258-41-2]5-Amino-1,10-phenanthroline</strong> (0.49 g, 2.501 mmol, 1.0 equiv.) was dissolvedin toluene (30 mL) and heated to reflux. Bromopentacarbonylrhenium(I) (1.00 g, 2.462 mmol, 1.0 equiv.) was then added to the reaction mixture, whereupon the solution turned from yellow to orange. The reaction mixture was stirred under refluxunder a constant supply of nitrogen gas for 1 h. The solution wasthen cooled to room temperature and filtered via vacuum filtration,whereafter the precipitate was washed with n-hexaneand dried to afford an orange powder (1.27 g, 93 %); mp 318-3198C (dec.). dH (400 MHz, [D6]DMSO) 9.40 (dd, Jd 5.12, 1.20,1HAr), 9.11 (dd, Jd 8.52, 1.20, 1HAr), 8.95 (dd, Jd 5.00, 1.28,1HAr), 7.24 (dd, Jd 8.44, 1.20, 1HAr), 8.05 (dd, Jd 8.52, 5.12,1HAr), 7.79 (dd, Jd 8.36, 5.0, 1HAr), 7.07 (s, 1HAr), 6.90 (s, br,1HNH2). dC (100 MHz, [D6]DMSO) 197.50, 197.39, 189.59,153.35, 148.04, 146.68, 144.89, 139.65, 135.54, 134.29, 132.68,126.19, 125.00, 123.56, 101.18. nmax/cm1 (attenuated totalreflectance (ATR) corrected) 3491.45 (w, asym N-H str),338.00 (w, sym N-H str), 3235.51 (w, sp2 C-H str), 2012.36(s, sh, A0(1) CO str), 1921.25 (s, A0(2) CO str), 1894.37(s, A00 CO str). m/z (LRMS ESI, cone 60 V) 466.17[M - Br]; calc. 466.02; 546.05 and 457.05 [MH]; calc.545.95 and 547.94. m/z (HRMS ESI) 466.01988 [M-Br];calc. 466.01959 (D 0.61 ppm). lmax/nm (e/M1 cm1) (CH3CN)416 (2726), 348 (10142), 296 (24429), 244 (36534), 194(58783). Anal. Calc. for ReC15H9O3N3Br: C 33.04, N 7.71, H1.66, Br 14.65; found C 33.06, N 7.64, H 1.80, Br 14.39 %. |
In toluene;Reflux; | General procedure: The preparation of 1 and 2 (Scheme 2) was carried out accordingto literature procedures [6,25,34,43,44]. In a typical procedure,1 equivalent of the Re-precursor (in our case Re(CO)5Br) and 1equivalent of the diimine were brought to reflux for several hoursin toluene and filtered hot. These syntheses usually resulted in analytically pure products after one recrystallization from hottoluene or dichloromethane/hexane mixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With acetic acid; In chloroform; for 24h;Inert atmosphere; Reflux; | Compound 3 (0.45g, 0.78mmol) dissolved in CHCl3 (20mL) and a catalytic amount of acetic acid were mixed and stirred for 20min, then 5-amino-1,10-phenanthroline (0.38g, 1.94mmol) dissolved in CHCl3 (25mL) was added dropwise into the above mixture. The mixture was refluxed for further 24h under a dry nitrogen protection. After cooled to rt, poured into ice-water (50mL), extracted with CHCl3 (60mL), and then washed with saturated brine. The combined organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated, and the residue was purified by column chromatography over silica gel using CH2Cl2/ethyl acetate (v/v=10:1) as eluent to give 0.4g with a yield of 55% as a light-yellow powder. Mp: 111-112C. 1H NMR (400MHz, CDCl3, TMS, deltappm): 9.25-9.23 (d, J=10.4Hz, 2H), 9.15 (s, 2H), 8.83-8.79 (t, 2H), 8.69-8.67 (d, J=8.8Hz, 2H), 8.32-8.25 (m, 4H), 8.12-7.99 (t, 6H), 7.83-7.79 (t, 2H), 7.73-7.51 (m, 10H), 7.38-7.34 (t, 6H), 1.40 (s, 9H). 13C NMR (100MHz, CDCl3, TMS, deltappm): 26.93, 31.56, 122.24, 122.80, 123.24, 123.56, 123.79, 126.09, 126.25, 126.27, 126.82, 127.34, 127.38, 127.49, 128.51, 129.06, 130.68, 131.15, 132.73, 135.56, 145.25, 148.03, 149.18, 150.18, 150.64, 160.30. TOF-MS (H+): 932. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | 1,10-Phenanthrolin-5-amine (0.100 g, 0.51 mmol), methyl 8-chloro-8-oxooctanoate (0.158 g, 0.76mmol) and 4-dimethylaminopyridine (0.01 g, 0.051 mmol) were dissolved in DMF (7 mL) and stirredfor 16 h at room temperature under an inert atmosphere. The volume of solution was reduced by 70%and added dropwise to a stirring solution of diethyl ether (10 mL). The filtrate was decanted and theprecipitate dried under vacuum. The solid was suspended in MeOH : hydroxylamine solution 50% (5mL) and 1M NaOH solution was added (0.5 mL) with stirring for 30 min. The solution was neutralisedto pH 7 and a precipitate formed on standing. The filtrate was decanted and the resulting solid driedunder vacuum to give a beige solid (0.061 g, 32%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In dichloromethane; at 20℃; for 16h; | General procedure: [{eta5-C5H4(C5F4N)}Mo(CO)2(NCMe)2][BF4] (6; 60 mg; 112 mumol) was dissolved in CH2Cl2 (10 mL) and treated with 1,10-phenanthroline (21 mg, 116 mumol). The solution was stirred for 16 h at room temperature. After that, the solvent was vacuum evaporated. The crude product was washed with ether, recrystallized from the mixture CH2Cl2/ether and vacuum dried. Yield: 64 mg (101 mumol, 90. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With ammonium sulfate; In methanol; at 65℃; for 24h; | General procedure: 4.2.1.4. Method D. A stirred solution of the 5-amino-1,10-phenanthroline (195 mg, 1 mmol), the monosaccharide (3 mmol) and ca. 4 mg of (NH4)2SO4 in 16 mL of MeOH was heated at 65 C for 24 or 48 h. During this time a pale yellow precipitate was accumulated. The reaction mixture was cooled and the solid obtained was separated by filtration and washed with MeOH (2 x 10 mL) and H2O (2 x 10 mL) to eliminate excess of sugar and possible traces of the starting amine and/or other by-products as well to remove the (NH4)2SO4 salt, followed by Et2O. This protocol provided pure N-(1,10-phenanthrolin-5-yl)-beta-glycopyranosyl amines 2a, 2c and 2d. For derivatives 2b and 2e the starting sugar could not be completely removed and a subsequent purification was required. The product was preadsorbed on silica gel and purified by flash chromatography. After drying in vacuum the purity of the products was checked by TLC, 1H NMR and analytical data. Derivatives 2a-e were obtained as monohydrates and exhibited poor solubility in water and organic solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With ammonium sulfate; In methanol; at 65℃; for 24h; | General procedure: 4.2.1.4. Method D. A stirred solution of the 5-amino-1,10-phenanthroline (195 mg, 1 mmol), the monosaccharide (3 mmol) and ca. 4 mg of (NH4)2SO4 in 16 mL of MeOH was heated at 65 C for 24 or 48 h. During this time a pale yellow precipitate was accumulated. The reaction mixture was cooled and the solid obtained was separated by filtration and washed with MeOH (2 x 10 mL) and H2O (2 x 10 mL) to eliminate excess of sugar and possible traces of the starting amine and/or other by-products as well to remove the (NH4)2SO4 salt, followed by Et2O. This protocol provided pure N-(1,10-phenanthrolin-5-yl)-beta-glycopyranosyl amines 2a, 2c and 2d. For derivatives 2b and 2e the starting sugar could not be completely removed and a subsequent purification was required. The product was preadsorbed on silica gel and purified by flash chromatography. After drying in vacuum the purity of the products was checked by TLC, 1H NMR and analytical data. Derivatives 2a-e were obtained as monohydrates and exhibited poor solubility in water and organic solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonium sulfate; In methanol; at 65℃; for 24h; | General procedure: 4.2.1.4. Method D. A stirred solution of the 5-amino-1,10-phenanthroline (195 mg, 1 mmol), the monosaccharide (3 mmol) and ca. 4 mg of (NH4)2SO4 in 16 mL of MeOH was heated at 65 C for 24 or 48 h. During this time a pale yellow precipitate was accumulated. The reaction mixture was cooled and the solid obtained was separated by filtration and washed with MeOH (2 x 10 mL) and H2O (2 x 10 mL) to eliminate excess of sugar and possible traces of the starting amine and/or other by-products as well to remove the (NH4)2SO4 salt, followed by Et2O. This protocol provided pure N-(1,10-phenanthrolin-5-yl)-beta-glycopyranosyl amines 2a, 2c and 2d. For derivatives 2b and 2e the starting sugar could not be completely removed and a subsequent purification was required. The product was preadsorbed on silica gel and purified by flash chromatography. After drying in vacuum the purity of the products was checked by TLC, 1H NMR and analytical data. Derivatives 2a-e were obtained as monohydrates and exhibited poor solubility in water and organic solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonium sulfate; In methanol; at 65℃; for 24h; | General procedure: 4.2.1.4. Method D. A stirred solution of the 5-amino-1,10-phenanthroline (195 mg, 1 mmol), the monosaccharide (3 mmol) and ca. 4 mg of (NH4)2SO4 in 16 mL of MeOH was heated at 65 C for 24 or 48 h. During this time a pale yellow precipitate was accumulated. The reaction mixture was cooled and the solid obtained was separated by filtration and washed with MeOH (2 x 10 mL) and H2O (2 x 10 mL) to eliminate excess of sugar and possible traces of the starting amine and/or other by-products as well to remove the (NH4)2SO4 salt, followed by Et2O. This protocol provided pure N-(1,10-phenanthrolin-5-yl)-beta-glycopyranosyl amines 2a, 2c and 2d. For derivatives 2b and 2e the starting sugar could not be completely removed and a subsequent purification was required. The product was preadsorbed on silica gel and purified by flash chromatography. After drying in vacuum the purity of the products was checked by TLC, 1H NMR and analytical data. Derivatives 2a-e were obtained as monohydrates and exhibited poor solubility in water and organic solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With ammonium sulfate; In methanol; at 65℃; for 24h; | General procedure: 4.2.1.4. Method D. A stirred solution of the 5-amino-1,10-phenanthroline (195 mg, 1 mmol), the monosaccharide (3 mmol) and ca. 4 mg of (NH4)2SO4 in 16 mL of MeOH was heated at 65 C for 24 or 48 h. During this time a pale yellow precipitate was accumulated. The reaction mixture was cooled and the solid obtained was separated by filtration and washed with MeOH (2 x 10 mL) and H2O (2 x 10 mL) to eliminate excess of sugar and possible traces of the starting amine and/or other by-products as well to remove the (NH4)2SO4 salt, followed by Et2O. This protocol provided pure N-(1,10-phenanthrolin-5-yl)-beta-glycopyranosyl amines 2a, 2c and 2d. For derivatives 2b and 2e the starting sugar could not be completely removed and a subsequent purification was required. The product was preadsorbed on silica gel and purified by flash chromatography. After drying in vacuum the purity of the products was checked by TLC, 1H NMR and analytical data. Derivatives 2a-e were obtained as monohydrates and exhibited poor solubility in water and organic solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,10-phenanthroline-5-amine With potassium hydrogencarbonate In dichloromethane for 0.166667h; Schlenk technique; Stage #2: diphenylacetic acid chloride In dichloromethane at 20℃; for 1h; Schlenk technique; | N-(1,10-phenanthrolin-5-yl)-2,2-diphenylacetamide (ligand 4 or PHMD) One hundred milligrams (0.513 mmol) of 1,10-phenanthroline-5-amine and 200 mg of dry KHCO3 in 3ml of dry DCM were added in a 25ml Schlenk tube and stirred for 10 min to dissolve the amine. One hundred and thirty milligrams (1.11 equiv.) of 2,2-diphenylacetyl chloride was dissolved in 2ml DCM and added dropwise to the Schlenk tube and stirred for 1 h at room temperature. The solvent was evaporated and the reaction mixture was poured in 20ml distilled water and extracted with DCM thrice (10 ml). The crude reaction mixture was purified with column chromatography by using 20% ethanol and 80% hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With trifluoroacetic acid; at 20℃; for 18h;Darkness; | 5-Aminophenanthroline(3, 1 g, 5.1 mmol) and paraformaldehyde (323 mg,10.8 mmol, 2.1 equiv) were mixed in a round-bottomed flask in the dark and cooled with an ice bath. Trifluoroacetic acid (15.2 mL, 133.2 mmol, 26 equiv) was added and the resulting mixture was stirred for 18 h in the dark. After that time the reaction mixture was added drop wise into water (200 mL). After cooling to room temperature the resulting suspension was carefully neutralized with a 6 N aq NaOH solution. The precipitate was collected by filtration, and dried in vacuum. The product was recrystallized from acetone to give the solid product (967 mg, 63%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Amixture of 5-amino-1,10-phenanthroline (1.85 g, 9.5mmol),2,4-dimethoxy-benzaldehyde (1.57 g, 9.5 mmol) and 6 mLglacial acetic acid in 150 mL anhydrous methanol wasrefluxed for 24 h with stirring. After cooling, NaBH4(1.78 g, 47.5 mmol) was added, and the mixture was stirredin an ice-water bath for 1 h and further refluxed for 3 h. Thesolvent was evaporated, and the residue was dissolved in150 mL chloroform. The solution was washed once with saturatedNa2CO3 solution (100 mL) and 3 times with distilledwater (100 mL). After organic phase was dried with Na2SO4and evaporated, the product was obtained as a red solid(2.53 g, 77 % yield). 1H NMR (400 MHz, CDCl3): delta=3.80(s, 3H), 3.85 (s, 3H), 4.45 (s, 2H), 4.84 (s, 1H), 6.45~6.47 (m,1H), 6.52 (s, 1H), 6.74 (s, 1H), 7.26 (t, J=4.0Hz, 1H), 7.42~7.57 (m, 1H), 7.95~7.97 (m, 1H), 8.23~8.25 (m, 1H), 8.86~8.87 (m, 1H), 9.13 (d, J=4.0Hz, 1H). 13C NMR (100 MHz,CDCl3): delta=43.50, 55.41, 55.44, 98.76, 100.60, 104.16,118.44, 122.09, 122.28, 123.24, 128.70, 130.14, 130.46,133.71, 141.22, 141.67, 146.24, 146.70, 149.76, 158.59,160.59. ESI-MS (m/z): 346.1 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In ethanol Reflux; | 9 General synthesis of 4-aza-3-hydroxy-1,2-trans-2,3-cis-lactone podophyllotoxin derivatives General procedure: These derivatives were synthesised by following a previously reported method [13]. An equimolar mixture of commercially available tetronic acid, 1,10 phenanthroline amine and the corresponding aromatic aldehyde was dissolved in ethanol. The reaction mixture was heated under reflux for 2-6h. After cooling, the solvent was removed in vacuo and the product was recrystallised from methanol to afford the desired compounds in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In ethanol;Reflux; | General procedure: These derivatives were synthesised by following a previously reported method [13]. An equimolar mixture of commercially available tetronic acid, 1,10 phenanthroline amine and the corresponding aromatic aldehyde was dissolved in ethanol. The reaction mixture was heated under reflux for 2-6h. After cooling, the solvent was removed in vacuo and the product was recrystallised from methanol to afford the desired compounds in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In ethanol Reflux; | 15 General synthesis of 4-aza-3-hydroxy-1,2-trans-2,3-cis-lactone podophyllotoxin derivatives General procedure: These derivatives were synthesised by following a previously reported method [13]. An equimolar mixture of commercially available tetronic acid, 1,10 phenanthroline amine and the corresponding aromatic aldehyde was dissolved in ethanol. The reaction mixture was heated under reflux for 2-6h. After cooling, the solvent was removed in vacuo and the product was recrystallised from methanol to afford the desired compounds in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol;Reflux; | General procedure: These derivatives were synthesised by following a previously reported method [13]. An equimolar mixture of commercially available tetronic acid, 1,10 phenanthroline amine and the corresponding aromatic aldehyde was dissolved in ethanol. The reaction mixture was heated under reflux for 2-6h. After cooling, the solvent was removed in vacuo and the product was recrystallised from methanol to afford the desired compounds in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In ethanol;Reflux; | General procedure: These derivatives were synthesised by following a previously reported method [13]. An equimolar mixture of commercially available tetronic acid, 1,10 phenanthroline amine and the corresponding aromatic aldehyde was dissolved in ethanol. The reaction mixture was heated under reflux for 2-6h. After cooling, the solvent was removed in vacuo and the product was recrystallised from methanol to afford the desired compounds in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In ethanol Reflux; | 8 General synthesis of 4-aza-3-hydroxy-1,2-trans-2,3-cis-lactone podophyllotoxin derivatives General procedure: These derivatives were synthesised by following a previously reported method [13]. An equimolar mixture of commercially available tetronic acid, 1,10 phenanthroline amine and the corresponding aromatic aldehyde was dissolved in ethanol. The reaction mixture was heated under reflux for 2-6h. After cooling, the solvent was removed in vacuo and the product was recrystallised from methanol to afford the desired compounds in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In ethanol; at 80℃; for 12h; | A mixture of 4,4'-diformyl-2,2'-bipyridine (234 mg,1.10 mmol) and 5-amino-1,10-phenanthroline (669 mg,3.43 mmol) in ethanol (50 mL) was heated to 80 C for12 h, giving a suspension. The reaction mixture was filtered hot, and the solid was washed with hot ethanol, affording the desired product as a yellow solid. Yield:486 mg (78 %). ESI-MS: m/z = 567.4 (M + H)+. 1HNMR (400 MHz, CDCl3): d = 7.68 (dd, J = 8.0, 4.8 Hz,2H), 7.74 (dd, J = 8.0, 4.4 Hz, 2H), 8.07 (dd, J = 5.2,1.2 Hz, 2H), 8.29 (dd, J = 2.8, 1.6 Hz, 2H), 8.31 (dd,J = 3.2, 1.6 Hz, 2H), 8.83 (dd, J = 8.4, 1.6 Hz, 2H), 8.88(s, 2H), 8.98 (d, J = 4.8 Hz, 2H), 9.07 (s, 2H), 9.19 (dd,J = 4.4, 2.0 Hz, 2H), 9.28 (dd, J = 4.4, 2.0 Hz, 2H). IR numax (KBr, cm-1): 3417 (br), 1628m, 1597s, 1554m,1505w, 1424m, 1383s, 1297w, 1206w, 1143w, 1062m,987w, 805w, 741s, 708w, 623w, 541w. Found: C 76.0, H3.8, N 19.7; Calcd for C36H22N8: C 76.3, H 3.9, N 19.8 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In ethanol; at 80℃; for 12h; | General procedure: A mixture of 4,4'-diformyl-2,2'-bipyridine (234 mg,1.10 mmol) and 5-amino-1,10-phenanthroline (669 mg,3.43 mmol) in ethanol (50 mL) was heated to 80 C for12 h, giving a suspension. The reaction mixture was filtered hot, and the solid was washed with hot ethanol, affording the desired product as a yellow solid. Yield:486 mg (78 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In ethanol; at 80℃; for 12h; | General procedure: A mixture of 4,4'-diformyl-2,2'-bipyridine (234 mg,1.10 mmol) and 5-amino-1,10-phenanthroline (669 mg,3.43 mmol) in ethanol (50 mL) was heated to 80 C for12 h, giving a suspension. The reaction mixture was filtered hot, and the solid was washed with hot ethanol, affording the desired product as a yellow solid. Yield:486 mg (78 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.2% | With acetic acid; In ethanol; for 6h;Reflux; | <strong>[54258-41-2]5-Amino-1,10-phenanthroline</strong> (471 mg, 2.42 mmol) and 2,6-pyridinedicarbaldehyde (135 mg, 1 mmol) were refluxed in EtOH (20 mL) containing a catalytic amount of acetic acid for 6 h, giving a suspension. The reaction mixture was filtered hot, and the solid was washed with EtOH to afford the desired product as a yellow solid. Yield: 451 mg (92.2%). 1H NMR (300 MHz, CDCl3): delta = 7.48 (s, 2H), 7.65 (dd, J = 8.1, 4.5 Hz, 2H), 7.72 (dd, J = 8.4, 4.5 Hz, 2H), 8.14 (t, J = 7.5 Hz, 1H), 8.27 (d, J = 8.4 Hz, 2H), 8.57 (d, J = 7.5 Hz, 2H), 8.82 (d, J = 8.4 Hz, 2H), 8.96 (s, 2H), 9.17 (d, J = 3.9 Hz, 2H), 9.27 (d, J = 4.2 Hz, 2H). ESI-MS: m/z 490.4 (M+H)+, 512.4 (M+Na)+. IR numax (KBr, cm-1): 3399s (br), 1626s, 1593s, 1562m, 1501m, 1486m, 1453w, 1421s, 1385m, 1337w, 1298w, 1265w, 1209w, 1142w, 1061m, 993w, 977w, 941w, 866m, 799m, 738s, 679w, 626m, 526w, 458w, 412w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In ethanol; at 78℃; | A solution of 3 (118 mg, 0.5 mmol) and 6 (195.2 mg, 1 mmol) in ethanol (30 mL) was heated under reflux overnight. The yellow solid was filtered while the solution was hot, and washed with ethanol. The solid was dried under air to give analytically pure 1, 0.442 g, yield 75 %, mp: 313-316 C. 1H NMR (300 MHz, DMSO-d6) delta = 9.83 (s, 2H), 9.44 (d,J = 4.7 Hz, 2H), 9.33 (s, 2H), 9.20 (bs, 2H), 9.10 (d, J = 4.1Hz,2H), 8.91 (d, J = 4.2 Hz, 2H), 8.61 (d, J = 4.3 Hz, 2H), 8.54 (d,J = 8.2 Hz, 2H), 8.01 (bs, 2H), 7.90-7.82 (m, 4H); 1C NMR(150 MHz, CDCl3) delta = 158.9, 151.1, 150.8, 149.9,147.0146.4, 145.6, 138.0, 136.0, 132.6, 128.6, 126.1, 125.7,124.0, 123.5, 123.2, 122.5, 111.0, 105.8; FTIR-ATR (cm-1):3062, 3045, 2986, 1586, 1558, 1502, 1484, 1421, 1394, 1292,1269, 1180, 1138, 1081, 1058, 1026, 971, 894, 865, 825, 804,757, 739, 714. Anal Calcd for C38H22N8: C, 77.27; H, 3.75;N,18.97; Found: C, 77.25; H, 3.78; N, 18.93; LCMS (m/z)Calcd. for C38H22N8: 590.20 [M+]; Found: 591.09 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium hydride; In tetrahydrofuran; at 20℃; for 3.5h;Inert atmosphere; | Sodium hydride (NaH) (0.044 g, 60%, 1.1 mmol) was added to a stirred solution of <strong>[54258-41-2]1,10-phenanthroline-5-amine</strong> (0.18 g, 0.94 mmol) dissolved in THF (20 mL) under an argon atmosphere. Compound (1) (0.5 g, 0.78 mmol) in THF (20 mL) was added dropwise to a stirred solution under an argon atmosphere for 30 min. The reaction mixture was stirred for 3 h at room temperature and the reaction was followed by TLC. The precipitated salt was then filtered off and the solvent was removed under reduced pressure and compound 2 was isolated by column chromatography silicagel 60 (230-400 mesh) as adsorbent and THF/n-hexane (1:1) as the eluent. Yield 0.3 g (60%). Anal. Calc. for [C42H33N6O5P3] Found: C,63.40; H, 4.08; N, 10.51%; requires: C, 63.48; H, 4.19; N,10.58%. MS (ESI) m/z (%) Calc.: 795.1798; found: 795.3481 (100) [M + H]+. 1H NMR (CDCl3, ppm) delta: 9.19 (s, 1H), 9.09 (s, 1H), 8.06 (d, J = 7.16 Hz, 1H), 7.82 (d, J = 14.22 Hz, 2H), 7.54 (d, J = 17.22 Hz, 2H), 7.18-7.14 (m, 5H), 7.07-6.98 (m, 20H), 5.43 (s, 1H, NH); {1H}13CNMR (CDCl3, ppm) delta:151.85, 151.00, 150.86, 150.30, 149.15, 146.78, 143.82, 136.12, 135.63, 132.93, 129.71, 129.64, 129.02, 128.51, 125.84, 125.26, 125.15, 123.63, 122.71, 121.57, 121.40, 121.24, 114.84; {1H}31P NMR (CDCl3, ppm), assigned as an AB2 spin system delta: 13.05 [dd, 1P,P(OPh)(phenanthroline),A], 9.6 [dd, 2P, P(OPh)2, B2], 2JP,P 83.4 Hz and 2JP,P 5.7 Hz. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With sodium acetate; In ethanol; at 20℃; for 0.5h; | General procedure: The [VIVO(L-2H)(NN)] complexes, where L=5-bromosalicylaldehyde glycine derivative (L1) or salicylaldehyde glycine derivative (L2) and NN = 2,2?-bipyridine (bipy), 1,10-phenanthroline (phen), 5-amine-1,10-phenanthroline (aminophen), 5,6-epoxy-5,6-dihydro-1,10-phenanthroline (epoxyphen), dipyrido[3,2-a: 2?,3?-c]phenazine (dppz) or [1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline (tdzp), were synthesized using the following general procedure: 0.50 mmol of glycine (42 mg) and 1.0 mmol of sodium acetate were dissolved in 2 mL of distilled water. 0.50 mmol of 5-Br-salicylaldehyde (100 mg) or salicilaldehyde (61 mg) and 0.50 mmol of NN (78 mg bipy, 98 mg phen, 98 mg aminophen, 98 mg epoxyphen, 141 mg dppz or 120 mg tdzp) were dissolved in 3 mL EtOH (MeOH for dppz). Both solutions were mixed; to this mixture a solution of 0.43 mmol VIVOSO4(108 mg) in 1 mL H2O was added dropwise. The reaction mixture was stirred at room temperature for 30 min. The orange-brown solids were separated by centrifugation, washed five times with 2 mL portions of H2O and dried under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: 2-(Thiophen-2-yl)quinoline was synthesized accordingto the previous report.25. The cyclometalatediridium(III) chloro-bridged dimers [Ir(ppy)2Cl]2 and[Ir(thq)2Cl]2 were prepared with 2-phenylpyridine (ppy)and 2-(thiophen-2-yl)quinoline (thq) respectively according to literature methods.26. The Ir(ppy)2(phen-NH2 and Ir(thq)2(phen-NH2) complexes were synthesized by reaction of chloro-bridged dimer [Ir(ppy)2Cl]2 and[Ir(thq)2Cl]2 with 5-amino-1,10-phenanthroline (phen-NH2) respectively (see Scheme 1). The solutions of [Ir(ppy)2Cl]2 (0.161 g, 0.15 mmol) combined with phen-NH2 (0.073 g, 0.375 mmol) and [Ir(thq)2Cl]2(0.194 g, 0.15 mmol) combined with phen-NH2 (0.073 g,0.375 mmol) in CH2Cl2-MeOH (15 mL, 2:1 v/v) were heated to reflux respectively. After 3-5 h, the red solutions were cooled to room temperature, then a 6-fold excess of potassium hexafluorophosphate was added and the mixture was further stirred for 1 h. The suspensions were filtered to remove insoluble inorganic salts. The solutions were evaporated to dryness under reduced pressure. The crude product of Ir(ppy)2(phen-NH2+PF-6 (complex 1)was chromatographed with CH2Cl2/acetone (20:1) to produce a yellow solid in a 73% yield. 1H NMR (400 MHz,CDCl3): = 691-6.94 (m, 4H), 6.97-7.05 (m, 4H),7.09 (s, 1H), 7.42-7.45 (t, 2H), 7,68-7.73 (m, 2H),7.84-7.88 (t, 2H), 7.90-7.93 (t, 2H), 8.12 (d, 1H), 8.22(d, 2H), 8.37 (d, 1H), 8.39 (d, 1H); The crude product ofIr(thq)2(phen-NH2)PF-6 (complex 2) was chromatographed with CH2Cl2/acetone (20:1) to produce a yellow solidin a 65% yield. 1H NMR (400 MHz, CDCl3: = 635(s, 2H), 6.85 (s, 1H), 6.92 (d, 2H), 7.17-7.21 (m, 4H),7.37-7.41 (t, 2H), 7.54-7.59 (m, 4H), 7.77-7.87 (m, 4H),7.98-8.07 (m, 4H), 8.31 (d, 1H), 8.71 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.7% | In tetrahydrofuran; at 70℃; for 3h; | 5)0.391 g (0.002 mol) of 5-amino-1,10-phenanthroline was weighedAnd 1.695 g (0.002 mol) of Eu (TTA) 3 · 2H2O,Put the two into the beaker,And dissolved in 50 mL of tetrahydrofuran (THF) (to ensure sufficient dissolution,You can use ultrasonic cleaning machine for half an hour to fully dissolve it)And then poured into a single-mouth flask,The flask was mounted on a DF-101S heated thermostatic heated magnetic stirrer,In the three-necked flask on the installation of reflux condenser,The oil bath temperature was set at 70 C,Stir with medium speed.After 3 hours of reaction,The flask was cooled to room temperature,The solvent was then distilled off under reduced pressure using a steaming vessel,Set the steaming temperature to 50 C.When the solvent is gradually distilled off,Gradually precipitate reddish brown solid.And then dried in a vacuum oven at 60 C for 12 hours,To obtain 1.873 g of a reddish brown solid powder,This solid powder is Eu (TTA) 3 · Phen-NH2,Yield 92.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.8% | With acetic acid; In ethanol; for 12h;Reflux; | General procedure: Both compounds were synthesized in the same way. A mixture ofthe appropriate aldehyde [thiophene-2,5-dicarbaldehyde (283 mg,2.02 mmol), furan-2,5-dicarbaldehyde (316 mg, 2.55 mmol)] and5-amino-1,10-phenanthroline [(1091 mg, 5.59 mmol) withthiophene-2,5-dicarbaldehyde, (1458 mg, 7.48 mmol) with furan-2,5-dicarbaldehyde] was refluxed in EtOH (50 mL) containing acatalytic amount of acetic acid for 12 h, giving a suspension. Thereaction mixture was filtered hot, and the solid was washed withEtOH to afford the desired product as a yellow solid.N,N0-[thiophene-2,5-diylbis(methan-1-yl-1-ylidene)]bis(<strong>[54258-41-2]1,10-phenanthroline-5-amine</strong>): Yield 926 mg, 92.8%. 1H NMR (400 MHz,CDCl3): d = 7.44 (s, 2H), 7.65 (dd, J = 8.0, 4.4 Hz, 2H), 7.69 (s, 2H),7.72 (dd, J = 8.0, 4.4 Hz, 2H), 8.27 (dd, J = 8.4, 1.6 Hz, 2H), 8.87(dd, J = 8.0, 1.6 Hz, 2H), 8.90 (s, 2H), 9.17 (dd, J = 4.4, 1.6 Hz, 2H),9.26 (dd, J = 4.4, 2.0 Hz, 2H). ESI-MS: m/z = 495.3 [M+H]+. IR mmax(KBr, cm1): 3423 (br), 1590 s, 1563m, 1503w, 1485w, 1423m,1384 s, 1239m, 1204w, 1143w, 1110w, 1060m, 973w, 874w,802w, 743m, 627w, 523w, 414w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.6% | With acetic acid; In ethanol; for 12h;Reflux; | General procedure: Both compounds were synthesized in the same way. A mixture ofthe appropriate aldehyde [thiophene-2,5-dicarbaldehyde (283 mg,2.02 mmol), furan-2,5-dicarbaldehyde (316 mg, 2.55 mmol)] and5-amino-1,10-phenanthroline [(1091 mg, 5.59 mmol) withthiophene-2,5-dicarbaldehyde, (1458 mg, 7.48 mmol) with furan-2,5-dicarbaldehyde] was refluxed in EtOH (50 mL) containing acatalytic amount of acetic acid for 12 h, giving a suspension. Thereaction mixture was filtered hot, and the solid was washed withEtOH to afford the desired product as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium hydrogencarbonate; In water; at 0℃; for 3h; | General procedure: To a vigorously stirred saturated aqueous solution of NaHCO3 (18 mL) at 0 C. was added <strong>[54258-41-2]1,10-phenanthroline-5-amine</strong> (400 mg, 2.05 mmol) followed by hexanoyl chloride (0.350 mL, 337 mg, 2.5 mmol) or octanoyl chloride (0.432 mL, 407 mg, 2.5 mmol) or decanoyl chloride (0.515 mL, 477 mg, 2.5 mmol). After continued stirring until completion of the reaction (3 h, monitored by TLC), the mixture was extracted with ethyl acetate (3*10 mL). The organic layer was then treated with a few drops of pyridine and washed successively with 5% aqueous HCl (10 mL), 5% NaHCO3 (10 mL) and water until neutral pH was achieved. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to provide the crude amide which was purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 20% | With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 120h;Inert atmosphere; | 3,5-bis(3-bromopropoxy)-N-(1,10-phenanthrolin-5-yl)benzamide To a flame dried flask cooled under argon was added 3,5-bis(3-bromopropoxy)benzoic acid (0.792 grams, 2.0 mmol) and the amino-phenanthroline (0.390 grams, 2.0 mmol). The two compounds were then taken up in 20.0 mL of anhydrous DMF (Aldrich) and HCTU (0.909 grams, 2.2 mmol) was added. After five minutes, diisopropylethylamine (1.1 mL, 6.0 mmol) was added. After five days of stirring at room temperature the reaction was concentrated, taken up in ethyl acetate and washed with sodium bicarbonate (saturated). Upon removal of the organic layer the aqueous was salted out, and washed twice more with ethyl acetate. Confirmation of no residual desired material was done by LCMS of the aqueous layer. Purification was done using a Teledyne ISCO C18 reverse phase chromatography (water with 0.1% formic acid/MeCN gradient) to afford the desired material. Approximate yield, 20% MS (ESI positive mode, observed mass 572, M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With pyridine; In benzene; at 20℃; | 5-Fluoroindole-2-carboxylic acid (1.27 g, 9.0 mmol)Added to benzene,Heated to reflux,Slowly added dropwise thionyl chloride,And heating the suspension to reflux min;then,The mixture was concentrated in vacuo until yellowish green crystals were precipitated,get5-Fluoroindole-2-carbonyl chloride.A solution of 5-fluoroindole-2-acid chloride in benzene was added dropwise to a solution of 5-amino-1,10-phenanthroline (1.9 g,9.0 mmol) in pyridine,And the resulting mixture was stirred at room temperature overnight;Set aside precipitation,The precipitate was filtered and collected,Then crystallized in ethanol solution,A khaki-colored solid,The yield was 2.918 g,Yield 91% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | YC-2 (0.5000 g, 1.236 mmol) and HATU (0.5091 g, 1.339 mmol) were dissolved in 7.5 mL of DMF.TEA (0.1355 g, 1.339 mmol) was added, and the mixture was stirred under nitrogen for 1-2 hours at room temperature.<strong>[54258-41-2]5-Amino-1,10-phenanthroline</strong> (0.2010 g, 1.030 mmol) was added, and the mixture was warmed to 60 C and allowed to react overnight.After the reaction has cooled to room temperature, spin dry to remove DMF.The mixture was mixed with silica gel and separated by column chromatography (eluent: DCM: MeOH = 40:1).0.3235 g of a yellow solid was obtained in a yield of 54%. | |
54% | YC-2 (0.5000 g, 1.236 mmol) and HATU (0.5091 g, 1.339 mmol) were dissolved in 7.5 mL of DMF, and TEA (0.1355 g, 1.339 mmol).Under a nitrogen atmosphere, after stirring at room temperature for 1-2 hours, 5-amino-1,10-phenanthroline was added.(0.2010 g, 1.030 mmol), warmed to 60 C, and allowed to react overnight.After the reaction was cooled to room temperature, the DMF was removed by spin-drying, the mixture was applied to silica gel, and the column was separated by chromatography (DCM:MeOH = 40:1).0.3235 g of a pale yellow solid was obtained with a yield of 54%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 24h; | Compound 3 was synthesized through a modification of a procedure reported in the literature [32].<strong>[54258-41-2]5-Amino-1,10-phenanthroline</strong> (488 mg, 2.50 mmol, 1 eq.) was dissolved in DCM (20 mL) atroom temperature. 6-Heptynoic acid (315 mg, 2.50 mmol, 1 eq.) was added, followed by1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 959 mg, 5.00 mmol, 2.0 eq.)and finally 4-dimethylaminopyridine (DMAP, 305 mg, 2.50 mmol, 1 eq.). The mixture was allowed tostir for 24 h. The solvent was removed under reduced pressure before H2O (50 mL) was added causingprecipitation of a white solid which was isolated by filtration. The resulting solid was redispersed inMeCN (10 mL) and again filtered before being collected by filtration under vacuum and dried underhigh vacuum to give a beige/white solid (637 mg, 2.10 mmol, 84.0%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In toluene;Schlenk technique; Inert atmosphere; Reflux; | General procedure: In a 100ml Schlenk flask provided with magnetic stirrer and a condenser under nitrogen, <strong>[32993-05-8]CpRuCl(PPh3)2</strong> (0.1g, 0.138mmol) and anhydrous 1,10-phenanathroline (0.027g, 0.151mmol) were dissolved in anhydrous toluene (6mL) and was stirred for 3hat room temperature to get a thick red solution. An orange solid was obtained on cooling at -20C, which was filtered and vacuum dried. Yield 45mg, 45%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 24h; | 1,10-Phenanthrolin-5-amine (0.5g, 2.56mmol) was dissolved in distilled dichloromethane (100mL) before the solution was cooled to 0C. Nonanoic acid (0.4g, 2.56mmol), EDCI (1.23g, 6.4mmol) and DMAP (0.31g, 2.56mmol) were added sequentially before the reaction mixture was stirred at 0C for another hour. The mixture was allowed to react at room temperature and stirred for 24h. The solvent was removed under reduced pressure and then purified by silica gel column chromatography using gradient elution of CH2Cl2/51 CH3OH (0 to 10%). Yield: 0.38g (47%). 1H NMR (400MHz, CDCl3) delta: 9.08 (dd, 2H), 8.29 (s, 1H), 8.11 (dd, 2H), 7.57 (dd, 2H), 2.55 (m, 2H), 1.82 (m, 3H), 1.29 (m, 10H), 0.89 (m, 3H). 13C NMR (100MHz, CDCl3), 172.59, 150.00, 149.54, 146.08, 143.98, 136.15, 128.36, 124.21, 123.51, 122.79, 119.89, 37.57, 29.37, 29.17, 25.75, 22.65, 14.11. HRMS found (calcd) for C21H24N3O (m/z): [M-H]-, 334.1903 (334.1919). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In N,N-dimethyl-formamide; at 20℃; for 24h; | <strong>[54258-41-2]5-Amino-1,10-phenanthroline</strong> (1.000 g, 5.128 mol, 1.0 equiv.)and ESF (847.0 mg, 7.7 mol, 1.5 equiv.) were dissolved in DMF(10 mL) and stirred at room temperature (24 h). The resultingorange solution was then poured into water (300 mL), causing ayellow solid to precipitate. The precipitate was isolated viavacuum filtration and washed with water to remove residualDMF. Further purification was achieved by dissolving the crudematerial in a minimum of DMSO and eluting through a 40-g C18 column using a gradient mobile phase of 0.1%TFA in water andacetonitrile (5 to 100% over 8 column volumes). The eluentscontaining the product were then combined, evaporated underreduced pressure, and dried by lyophilization to obtain a yellowpowder (1.125 g, 63 %); mp 200-2058C (dec.). dH (400 MHz,CDCl3) 9.21 (dd, Jd 4.32, 1.56, 1HAr), 8.96 (dd, Jd 4.32, 1.64,1HAr), 8.26 (dd, Jd 8.44, 1.52, 1HAr), 8.04 (dd, Jd 8.12, 1.64,1 HAr), 7.65 (dd, Jd 8.40, 4.32, 1HAr), 7.53 (dd, Jd 8.08, 4.32,1HAr), 7.53 (dd, Jd 8.08, 4.32, 1HAr), 6.71 (s, 1HAr), 5.03 (t, Jt6.08, 1HNH), 4.08 (app. q, Jq 12.16, 6.08, 2HCH2-SO2F), 3.89 (td,Jq 6.16, 4.48, 2HCH2). dC (100 MHz, CDCl3) 150.43, 147.44,146.91, 142.31, 138.96, 129.59, 128.51, 123.27. 122.58, 122.02,101.11, 49.66 (J 15.08 Hz), 38.08. dF (376 MHz, CDCl3) 70.67(t, Jt 4.63). nmax/cm1 3402.28 (w, br, N-H str), 2933.34 (m, sp2C-H str), 2872.24 (m, sp3 C-H str), 1595.69 (s, sh, asym S=Ostr), 1384.34 (s, sh, sym S=O str), 818.10 (m, S-F str). m/z(LRMS ESI) 306.23 [MH]; calc. 306.07. m/z (HRMSESI) 306.07093 [MH]; calc. 306.07070 (D 0.74 ppm).lmax/nm (e/M1 cm1) (CH3CN) 331 (9098.68), 279(28578.41), 259 (21861.26), 221 (41646.31), 194 (22288.72).Anal. Calc. for C14H12O2N3SF: C 55.07, N 13.76, H 3.96; foundC 54.54, N 13.64, H 3.63 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | General procedure: Complexes were synthesized using the following general procedure: to an ethanolic (or methanolic) solution of glycine (1mmol) and NaOH (1mmol) salicylaldehyde (1mmol) was added. The resulting yellow solution was stirred for 30min at room temperature and a solution of Zn(CH3COO)2.2H2O (1mmol in 5mL of water) was added dropwise. The pH was adjusted to 7 with 1M NaOH and the mixture was stirred at room temperature for 1h. The polypyridyl (1mmol) in ethanol (10mL) was then added and the resulting solution stirred at room temperature for 1h, subsequently concentrated and left overnight at 4C. The precipitate obtained was filtered, washed with cold ethanol and diethyl ether and dried in vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In N,N-dimethyl-formamide; at 135℃; for 24h;Inert atmosphere; | In the N2 environment, weigh 429mg PN (2.20mmol),396 mg of 1,8-naphthalic anhydride (2.00 mmol) and 106 mg of Na2CO3 (1.00 mmol) were dissolved in 10 mLIn DMF (N,N-dimethylformamide), the mixture was heated to 135 C and stirred for 24 h.When cooling to 80 C, add 25mL of ethanol and stir for 1h, suction filtration,Further washing with ethanol until the precipitate became milky white gave the product PNN (1,8-naphthalic anhydride-N-1,10-phenanthroline). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With acetic acid; In ethanol; at 80℃; for 24h; | Amixture of 5-amino-1,10-phenanthroline (585mg, 3.0mmol) and 1,8-naphthyridine-2,7-dicarbaldehyde(186mg, 1.0mmol) in anhydrous EtOH (80mL) was heated at 80 C, then 10 drops of HOAc were added.The mixture was refluxed for 24 h. A suspension was obtained. The yellow precipitate was collectedby filtration, washed with hot EtOH, and dried in vacuo. Yield: 463 mg (88%) of a yellow solid.1H-NMR (400 MHz, DMSO-d6) = 7.79-7.91 (m, 6H), 8.55-8.57 (m, 2H), 8.76-8.79 (m, 6H), 8.96-8.99(m, 2H), 9.13-9.17 (m, 4H), 9.24-9.26 (m, 2H). ESI-MS m/z = 540.65 [M + H]+, 562.21 [M + Na]+.Theoretical exact mass: m/z = 540.18 [M + H]+, 563.17 [M + Na]+. Found: C, 74.4; H, 3.8; N, 20.8.Calculated for C34H20N8: C, 74.5; H, 3.7; N, 20.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Acridine-9-carboxylic acid (50 mg, 0.2 mmol), DCC (51 mg, 0.22 mmol), and HOBt (33.2 mg, 0.22 mmol) were dissolved in DMF under N2 atmosphere and stirred at RT for about 2 h. To this solution, <strong>[54258-41-2]1,10-phenanthroline-5-amine</strong> (48 mg, 0.22 mmol) in DMF was added and stirring was continued for 2 days under N2. The solution was filtered and poured into crushed ice when a beige coloured precipitate appeared, which was then filtered, washed with ice water, and dried. (Scheme 2). Yield: 70 mg (71%); IR (KBr): 3330 cm-1( N-H), 1717 cm-1( C = O), 1618 cm-1 ( C = N), 1575 cm-1 (C = C); UV (DMF, lambdamax) 260 nm (pi-pi*), 331 nm (n-pi*), 345 nm (n-pi*), 363 nm (n-pi*), 390 nm (n-pi*); ESI-MS(Q-Tof): m/z 401.1403. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Cyclometallated iridium(III) chloride-bridge dimer 6 (0.2084 g,0.0761 mmol) and 5-amino-1,10-phenanthroline (0.0297 g, 0.1522mmol) was dissolved in dichloromethane and methanol solution (50 mL,v: v 1:1), the mixture solution were refluxed at 80 C for 6 h. Aftercooling to room temperature, the NH4PF6 (0.062 g) was added, uponstirring for another 2 h and concentrated under vacuum to yield thecrude product, which was purified by neutral alumina column chromatographyusing CH2Cl2 and acetone (v: v 20:1) as eluent to obtaincomplex 2oo (0.2017 g, yield 80%). 1H NMR (400 MHz, (CD3)2SO,ppm): 1.88 (s, 3H, CH3), 1.91 (s, 6H, CH3), 2.30 (s, 3H, CH3), 6.28(d, 1H, J 12.0 Hz), 6.39 (t, 1H, J 10.0 Hz), 6.60 (s, 1H), 6.68 (s, 1H),7.00(s, 2H), 7.16 (m, 4H), 7.28 (t, 2H, J 8 Hz), 7.34-7.43 (m, 3H),7.48 (t, 3H, J 11.4 Hz), 7.53-7.59 (m, 2H), 7.67-7.76 (m, 2H), 7.84 (s,1H), 7.95-8.09 (m, 6H), 8.26 (s, 1H), 8.34 (s, 1H), 8.42 (t, 2H, J 10Hz), 9.04 (d, 1H, J 8 Hz). 13C NMR (100 MHz, (CD3)2SO, ppm):166.14, 166.05, 165.36, 161.22, 153.35, 150.66, 149.62, 149.23,147.85, 146.9, 145.66, 145.53, 144.29, 144.10, 143.08, 143.03, 141.79,141.39, 141.37, 140.68, 140.37, 139.78, 139.69, 138.87, 138.63,137.60, 137.30, 135.21, 134.46, 134.26, 133.87, 133.42, 133.22,132.65, 132.39, 129.40, 129.30, 127.13, 126.98, 126.70, 126.23,125.68, 125.25, 124.80, 124.34, 124.01, 122.58, 121.34, 121.12,120.32, 119.68, 119.48, 119.14, 118.85, 113.26, 101.80, 65.05, 64.55,32.00, 31.23, 30.30, 29.90, 29.04, 28.96, 28.64, 28.54, 26.59, 25.05,23.80, 22.33, 22.03, 14.56 ( CH3), 14.10 ( CH3). IR (KBr, cm 1): 3440( NH2), 3395 ( NH2). Malditof-HRMS (m/z): [M-PF6] calcd forC72H45F12IrN5S4, 1528.2; found, 1528.199988. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With dmap; In N,N-dimethyl-formamide; for 9h;Inert atmosphere; | The compound was prepared by the slight modification of theappropriate literature method [23]. 1.93 g (10.0 mol) of 5-amino-1,10-phenanthroline and 122 mg (100 mmol) of DMAP were dissolvedin 70 mL dry DMF under nitrogen atmosphere at roomtemperature. The mixture of 1.52 mL (10.0 mol) of methyl-4-(chloroformyl)butyrate, and 30 mL dry DMF was added dropwiseto the reaction in 1 h. The mixture was stirred for 8 h and thenevaporated to 10 mL.100mL dry Et2Owas added to the mixture andcooling at 4 C overnight afforded a beige precipitate. The solid wasfiltered and dried in vacuo. Yield: 3.233 g, 99%. 1H NMR: (400 MHz,D2O): delta/ppm 9.20 (d, 1H, Ar-H); 9.13 (d, 1H, Ar-H); 8.92 (d, 1H, Ar-H); 8.75 (d, 1H, Ar-H); 8.19 (s, 1H, Ar-H); 8.16 (m, 1H, Ar-H); 8.09 (m,1H, Ar-H); 3.74 (s, 3H, CH3); 2.75 (t, 2H, CH2); 2.61 (t, 2H, CH2); 2.14(m, 2H, CH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.3% | With acetic acid; In methanol; at 60 - 65℃; for 4h; | To a solution of 5-bromo-2-hydroxybenzaldehyde (75 mg, 0.37 mM) in 20 mL of dry methanol,about 100 L of acetic acid was added drop wise to act as a catalyst during the reaction. To this above solution, 20 mg (0.10 mM) of 1,10-phenanthrolin-5-amine was combined with the help of aglass syringe. During this addition, color change was observed from colorless to pale brown solution.The above reaction mixture was then refluxed under continuous stirring at 60-65 C for 4 h. After thecompletion of the reaction, the formed colored precipitate was filtered and washed several times withmethanol to get desired product.Yield: 186 mg (75.3%). m.p.: 234 C. 1H NMR (CDCl3, 400 MHz, ppm): delta 8.94 (s, 1H), 8.03 (dd, 2H,J = 14 Hz), 7.46 (dd, 2H, J = 8 Hz), 7.25-6.58 (m, 7H, Ar-H). 13C NMR (100 MHz): delta 167.75, 139.36,135.29, 133.46, 133.05, 132.81, 130.37, 128.88, 128.11, 128.08, 127.73, 127.68, 126.20 and 126.01. ESI-MScalculated for C19H12N3BrO [M]+: 377.02 and found is 377.10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.7% | With acetic acid; In methanol; at 60 - 65℃; for 4h; | To a solution of thiophene-3-carbaldehyde (83 mg, 0.42 mM) in 20 mL of dry methanol, about100 L of acetic acid was added drop wise to act as a catalyst during the reaction. To this abovesolution, 20 mg (0.10 mM) of 1,10-phenanthrolin-5-amine was combined with the help of a glasssyringe. During this addition, color change was observed from colorless to yellow colored solution.The above reaction mixture was then refluxed under continuous stirring at 60-65 C for 4 h. After thecompletion of the reaction, the formed colored precipitate was filtered and washed several times withmethanol to get desired product.Yield: 177 mg (72.7%). m.p.: 243 C. 1H NMR (CDCl3, 400 MHz, ppm): delta 8.99 (s, 1H), 7.84 (dd, 2H,J = 4 Hz), 7.71 (dd, 2H, J = 6 Hz), 7.69-6.08 (m, 6H, Ar-H). 13C NMR (100 MHz): delta 167.51, 137.73, 136.91,133.82, 132.35, 131.41, 130.09, 129.76, 129.00, 126.71 and 126.28. ESI-MS calculated for C17H11N3S [M]+:289.07 and found is 289.80. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane; at 20℃;Darkness; | A mixture of 0.100 g (0.364 mmol, 1 eq) of [Mn(CO)5Br] and0.071 g (0.364 mmol, 1 eq) of 1,10-phenanthroline-5-amine (1-L) in10 mL of dry degassed dichloromethane was allowed to stir overnightat room temperature in the dark. Partial removal of the solventunder reduced pressure followed by addition of diethyl etherresulted in the precipitation of a yellow solid, which was filtered,washed with diethyl ether and dried in vacuo.Yield: 127 mg (85%). 1H NMR (400 MHz, DMSO-d6) d 9.53 (d, J 3.9 Hz, 1H), 9.10 (d, J 3.6 Hz, 1H), 9.01 (d, J 7.2 Hz, 1H), 8.38 (d,J 7.7 Hz, 1H), 8.03 (t, J unresolved, 1H), 7.79 (t, J unresolved, 1H),7.02 (broad s, 1H), 6.77 (broad s, 2H, NH2) ppm. 13C NMR (100 MHz,DMSO-d6) d 169.0, 168.3, 154.0, 148.9, 147.1, 144.9, 140.4, 134.8,133.6, 132.4, 126.1, 124.8, 123.4, 101.2 ppm. IR (neat) 3493, 3328,3232, 2016 (vs, nCO), 1916 (vs br, nCO), 1639, 849, 725, 679,635 cm1. HRMS (ESI) m/z calcd. for C19H9MnN3O3 [M-Br]334.0019; found 334.0009. |
Tags: 54258-41-2 synthesis path| 54258-41-2 SDS| 54258-41-2 COA| 54258-41-2 purity| 54258-41-2 application| 54258-41-2 NMR| 54258-41-2 COA| 54258-41-2 structure
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