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CAS No. : | 57709-62-3 | MDL No. : | MFCD00774291 |
Formula : | C14H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RHXOPVFYZBGQGA-UHFFFAOYSA-N |
M.W : | 236.23 | Pubchem ID : | 602123 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 14 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 67.82 |
TPSA : | 59.92 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.29 cm/s |
Log Po/w (iLOGP) : | 0.54 |
Log Po/w (XLOGP3) : | 2.05 |
Log Po/w (WLOGP) : | 2.41 |
Log Po/w (MLOGP) : | 0.52 |
Log Po/w (SILICOS-IT) : | 3.25 |
Consensus Log Po/w : | 1.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.04 |
Solubility : | 0.216 mg/ml ; 0.000913 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.94 |
Solubility : | 0.273 mg/ml ; 0.00116 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.91 |
Solubility : | 0.00292 mg/ml ; 0.0000124 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.53 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P422-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
95% | With selenium(IV) dioxide In 1,4-dioxane for 1h; Heating; | |
94% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux; | |
94% | With selenium(IV) dioxide In tetrahydrofuran; lithium hydroxide monohydrate for 5h; Reflux; | 1.1; 2.1; 3.1; 4.1; 5.1; 6.1 (1) Under stirring conditions, SeO2 (5.3g, 48mmol) was added to a composite solvent consisting of 120mL tetrahydrofuran and 10mL water, heated to reflux, and then added dropwise 2,9-dimethyl-1,10-o The tetrahydrofuran solution of phenanthroline [obtained from 2,9-dimethyl-1,10-phenanthroline (5.0g, 24mmol) dissolved in 150mL tetrahydrofuran], after the addition is complete, react for 5.0h, then take advantage of Hot filtration, the obtained filtrate is left to cool until a solid precipitates, and then the filtrate is filtered to obtain a reddish brown flocculent solid, namely 2,9-diformaldehyde-1,10-phenanthroline (5.0g, yield 94%) |
93% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux; | |
88% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux; | |
86% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 0.5h; Reflux; Inert atmosphere; Schlenk technique; | Synthesis of 2,9-dicarbaldehyde-1,10-phenanthroline The ligand was synthesized from a modified literature procedure [52]: To a solution of selenium oxide (2.26 g, 20.41 mmol) in deionized water (5 mL) and 1,4-dioxane (70 mL), 2,9-dimethyl-1,10-phenanthroline (2.00 g, 9.60 mmol) in 1,4-dioxane (20 mL) was added in a dropwise manner. The reaction mixture was refluxed for 0.5 h, during which the color of the reaction mixture changed from yellow to reddish brown with black deposits. Upon cooling to room temperature, the brown solids were collected by suction filtration and washed with Et2O (10 mL × 3). These solids were further purified by recrystallization with warm CHCl3and allowed to cool and stand overnight. Yellowish orange solids were collected by suction filtration and washed with Et2O (10 mL × 3) to give 2,9-dicarbaldehyde-1,10-phenanthroline.1H-NMR signals are consistent with that of the literature reported [50]. Yield: 1.95 g, 86%. |
85% | With selenium(IV) oxide In 1,4-dioxane for 0.166667h; Heating; microwave; | |
85% | With selenium(IV) dioxide In 1,4-dioxane for 2h; Reflux; | |
85% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 0.5h; Reflux; | |
85% | With selenium(IV) dioxide In 1,4-dioxane at 60 - 100℃; for 14.5h; | |
85% | With selenium(IV) dioxide In 1,4-dioxane at 85℃; for 6h; | |
85% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate at 20℃; for 0.333333h; | 2.2. Procedure for synthesis of compound 2 Neocuproine (14.4 mmol, 1 equiv., 3 g) was dissolved in dioxane(50 mL) and water (2 mL), and the resulting solution was stirred for20 min. at room temperature. A suspension of selenium dioxide(64.8 mmol, 4.5 equiv., 7.19 g) in a mixture of dioxane (130 mL)and water (5.2 mL) was then added, and the color changed frombrown to white. The resulting suspension was refluxed for 24 h,and then the black colored precipitate (selenium metal) was filteredwhile hot. The resulting solution was cooled and the resultingprecipitate was filtered to give the desired compound whichwas purified by crystallization from acetone. |
81% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux; | |
81.75% | With selenium(IV) dioxide In 1,4-dioxane for 12h; | 2.2.1. Synthesis of 1,10-phenanthroline-2,9-dicarbaldehyde 1,10-Phenanthroline-2,9-dicarboxaldehyde was synthesized accordingto a previously reported method [36-40]. To a double-mouthedround bottom flask, 30 mL of a dioxane solution dissolved in seleniumdioxide (4.5 g, 40.55 mmol) was added and placed in a water bath. Witha constant-pressure drop funnel, 100 mL of dioxane solution dissolved inneocopper reagent (3 g, 14.40 mmol) was added drop by drop to thedouble-bottomed flask. After 12 h in the water bath reaction, while hotfilter out the tar and selenium collection filtrate, the filtrate was yellow.When the filtrate was cooled, a large number of yellow precipitates weregenerated, namely 1,10-phenanthroline-2,9-dicarboxaldehyde crudeproduct. After filtering out the crude product, it was collected and dissolvedin benzene, to which n-hexane was added for recrystallization.Finally, the resulting product was filtered and dried to obtain a goldenyellow needle-like solid. Golden yellow needle-like solid 3.1313 g, yield:81.75%. M.p.: 238-240 C. Anal. Calcd. for C14H8N2O2 (%): C, 71.18; H,3.41; N, 11.86. Found: C, 71.29; H, 3.25; N, 11.62. 1H NMR (500 MHz,DMSO) δ 10.36 (d, J = 0.8 Hz, 1H), 8.80 (dd, J = 8.2, 0.8 Hz, 1H), 8.32(d, J = 8.2 Hz, 1H), 8.29 (s, 1H). |
80.56% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 3h; Reflux; | 2.1.1 2,9-Dicarboxylic acid-1,10-phenanthroline Selenium oxide (13.5 g, 0.12 mol) and 2,9-dimethyl-1,10-phenanthroline (5 g, 0.02 mol) were added into a mixture of1,4-dioxane (320 mL) and ultra-pure water (50 mL) in a500 mL of round-bottom flask. The reaction remained underreflux for 3 h and filtered while hot, then the filtrate was leftto cool. Golden product, 2,9-dicarbaldehyde-1,10-phenanthroline(4.62 g, 80.56%), was obtained after another filtration.Then, 2,9-dicarbaldehyde-1,10-phenanthroline (3 g,0.013 mol) was added into concentrated nitric acid (65%, 60 mL). After refluxing for 3 h, the solution was cooled bypoured onto the solid ice and the crude product was separatedout gradually. The crude product was filtered to get the solidproduct and dried before the next step |
80% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux; | |
74% | With selenium(IV) dioxide In 1,4-dioxane Inert atmosphere; | |
73% | With selenium(IV) dioxide In 1,4-dioxane at 20℃; for 2h; Reflux; | |
72% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 0.666667h; Reflux; | |
72% | With selenium(IV) dioxide In 1,4-dioxane for 0.666667h; Reflux; | |
72% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux; | |
70% | With selenium(IV) oxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Heating; | |
70% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux; | |
70% | With selenium(IV) dioxide In 1,4-dioxane for 2h; Reflux; | |
70% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux; | |
69% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux; | 2,9-dicarbaldehyde-1,10-phenanthroline. To a solution of 5.65 g (50.9 mmol) of selenium dioxide in 150 mL dioxane and 10 mL water was addeddropwise a solution of 5.0 g (24.0 mmol) 2,9-dimethyl-1,10-phenanthroline in 100 mL dioxane. Themixture was heated to reflux under magnetic stirring.The disappearance of 2,9-dimethyl-1,10-phenanthrolinewas followed by TLC with dichloromethane/methanol (8/2 v/v) as eluent. Thereaction was stopped when complete disappearance of the reactant was achieved (ca. 4 h).The mixture was filtrated on Celite while hot, the filtrate was allowed to cool and a brownsolid precipitated. It was collected by filtration, washed with dioxane and dried over vacuumto yield a brown solid (3.90 g, 69% yield). The product was engaged in the next step without further purification. |
67.1% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 1h; Reflux; | |
67.6% | With selenium(IV) dioxide In 1,4-dioxane at 110℃; for 2h; | |
63% | With selenium(IV) dioxide In dimethyl sulfoxide for 3h; Inert atmosphere; Reflux; | |
50% | With selenium(IV) oxide; lithium hydroxide monohydrate In 1,4-dioxane for 0.25h; Heating; | |
48% | With iodine; tert-Butyl iodide; trifluoroacetic acid In dimethyl sulfoxide at 148℃; for 2h; | |
47% | With selenium(IV) oxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Heating; | |
46.93% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux; | 2.2.1. 2,9-dicarbaldehyde-1,10-Phenanthroline This compound was prepared according to a literature method [34]with a slight modification. Selenium oxide (1.87 g, 0.05 mol) was addedinto a mixture of 1,4-dioxane (150 mL) and deionized water (10 mL) in a500 mL three necked-flask. After heating to refllux, a solution of 2,9-dimethly-1,10-phenanthroline (1.67 g, 0.024 mol) in 1,4-dioxane(100 mL) was added drop wise into the flask for over 10 min. The reactionwas allowed to run under reflluxf or 2 h then reaction was stoppedand the mixture was filtered while hot, the filtrate was allowed to cool atroom temperature. A yellow needle solid was obtained from filtrate afterfiltration. The solid was used directly for following reaction without anyfurther purification. Yield: 0.890 g, 46.93%. The structure wasconfirmed by 1H NMR. |
45% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux; | |
43% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 3h; Reflux; | |
34% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux; | |
With selenium(IV) oxide In 1,4-dioxane | ||
With selenium(IV) oxide In 1,4-dioxane for 3h; Heating; | ||
With selenium(IV) oxide In 1,4-dioxane for 2h; Heating; | ||
With selenium(IV) dioxide In 1,4-dioxane | ||
With selenium(IV) dioxide | ||
With selenium(IV) dioxide In 1,4-dioxane | ||
With selenium(IV) dioxide | ||
With selenium(IV) dioxide | ||
With selenium(IV) dioxide | ||
With selenium(IV) dioxide In 1,4-dioxane | ||
With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2.16667h; Reflux; | ||
With selenium(IV) dioxide In 1,4-dioxane | Synthesis of 1,10-phenanthroline-2,9-dicarboxylic acid bis-[(2-methoxyphenyl)amide] (1) General procedure: The oxidation of 2,9-dimethyl-1,10-phenanthroline with SeO2 in dioxane yielded 1,10-phenanthroline-2,9-dicarboxaldehyde which was further oxidized to 1,10-phenanthroline-2,9-dicarboxylic acid using concentrated HNO3.29 1,10-Phenanthroline-2,9-dicarboxylic acid (0.500 g, 1.86 mmol) was refluxed for two hours in excess SOCl2 (12 ml, 0.168 mol) and a drop of DMF was added in catalytic amount. SOCl2 was then removed at a reduced pressure resulting in diacyl chloride as pale yellow residue to which was added K2CO3 (0.567 g, 4.11 mmol), 2-methoxy aniline (0.506 g,4.11 mmol) and TBAHSO4 in catalytic amount and 25 ml of freshly dry distilled acetonitrile. The contents were refluxed until TLC monitoring indicated completion of the reaction. The contents were filtered and the solvent was vacuum evaporated to yield crude yellow solid. Recrystallization of crude product from mixture of methanol and chloroform resulted in the formation of pure amide. | |
With selenium(IV) dioxide In 1,4-dioxane for 4h; Reflux; | ||
With selenium(IV) oxide | ||
With selenium(IV) oxide In 1,4-dioxane; lithium hydroxide monohydrate | ||
0.6% | With selenium(IV) dioxide In 1,4-dioxane Heating; | |
With selenium(IV) dioxide In 1,4-dioxane for 1h; Heating; | ||
With selenium(IV) oxide In 1,4-dioxane for 0.5h; Reflux; | ||
With selenium(IV) dioxide In 1,4-dioxane Reflux; | ||
With selenium(IV) dioxide In 1,4-dioxane Reflux; Inert atmosphere; | ||
With selenium(IV) dioxide In 1,4-dioxane | ||
With selenium(IV) dioxide In 1,4-dioxane for 5h; Reflux; | First step A reaction mixture of 2,9-dimethyl-1,10-phenanthroline hemihydrate (10 mM)and selenium dioxide (10 mM) was placed in 100 mL of dioxane in a 250-mL round bottom(RB) flask. The mixture was manually stirred and allowed to reflux in a wax bath for 5 h. Thehot solution was filtered and a yellow-orange product separated from the filtrate. | |
With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate | ||
With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 2h; | ||
With selenium(IV) dioxide; lithium hydroxide monohydrate In 1,4-dioxane at 80℃; | 2.1. Synthesis General procedure: The V-shaped phenanthroline-based hexacatenars in which 1,10-phenanthroline was substituted on 2,9- positions with two cyanovinyl units were prepared according to Scheme 1. 1,10-phenanthroline-2,9-dicarbaldehyde 2[27] was synthesized by oxidationof 2,9-dimethyl-1,10-phenanthroline in the presence of SeO2 in 1,4-dioxane. 4-Hydroxybenzyl cyanide was etherified with benzylchlorides in the presence of K2CO3 in DMF to yield the key intermediate compounds 5/n.[22d,28] Compound 2 was reacted with 5/n under Knoevenagel reaction condition to yield the target compounds Phe/n. All the intermediate compounds and target compounds were purified by column chromatography, the chemical structures were determined by NMR spectra and element alanalysis. The detailed synthetic procedure and corresponding data were described in the ESI. Although some 3,8-disubstituted 1,10-phenanthroline-based polycatenar mesogens had been synthesized using Suzuki and Sonogashira coupling,[12] these Phe/n were the first examples of V-shaped hexacatenars which were synthesized by Knoevenagel reaction in high yields. | |
With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux; | ||
With selenium(IV) dioxide In 1,4-dioxane at 101.84℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With sodium periodate In dichloromethane; water at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium tetrahydroborate for 4h; Heating; | |
75% | With sodium tetrahydroborate In ethanol for 4h; Reflux; | |
74% | With sodium tetrahydroborate In ethanol for 1.5h; Inert atmosphere; Schlenk technique; Reflux; | Synthesis of 2,9-bis(hydroxymethyl)-1,10-phenanthroline The ligand was synthesized from a modified literature procedure [51]: To a solution of 2,9-dicarbaldehyde-1,10-phenanthroline (1.60 g, 6.77 mmol) in absolute EtOH (120 mL), anhydrous NaBH4(1.02 g, 27.09 mmol) was added. The reaction mixture was refluxed under argon for 1.5 h, during which the color of the reaction mixture changed from yellow to brown. Upon cooling to room temperature, the reaction mixture was removed by reduced pressure. The aqueous layer was extracted with EtOAc (50 mL × 2). The organic phases were combined, washed with brine (50 mL × 2), dried over anhydrous MgSO4, and concentrated to give 2,9-bis(hydroxymethyl)-1,10-phenanthroline as pale pink solids.1H-NMR signals are consistent with that of literature reported. Yield: 1.20 g, 74%. |
68% | With sodium tetrahydroborate In ethanol for 2h; Heating; | |
65.2% | With sodium tetrahydroborate In ethanol for 0.5h; Reflux; | |
With sodium tetrahydroborate In ethanol Heating; | ||
With sodium tetrahydroborate | ||
With sodium tetrahydroborate In ethanol for 2h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With pyridine; hydroxylamine hydrochloride In ethanol for 2h; Reflux; | |
78% | With pyridine; hydroxylamine hydrochloride In ethanol at 95℃; for 2h; | |
78% | Stage #1: 1,10-phenanthroline-2,9-dicarboxaldehyde With hydroxylamine hydrochloride In ethanol at 60 - 80℃; for 0.416667h; Stage #2: With pyridine In ethanol for 2h; Reflux; |
With hydroxylamine hydrochloride In pyridine; ethanol for 2h; Heating; | ||
With hydroxylamine hydrochloride; triethylamine In acetonitrile for 4h; Reflux; | ||
With hydroxylamine hydrochloride; triethylamine In acetonitrile | ||
With hydroxylamine hydrochloride; triethylamine In acetonitrile for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid; | General procedure: The oxidation of 2,9-dimethyl-1,10-phenanthroline with SeO2 in dioxane yielded 1,10-phenanthroline-2,9-dicarboxaldehyde which was further oxidized to 1,10-phenanthroline-2,9-dicarboxylic acid using concentrated HNO3.29 1,10-Phenanthroline-2,9-dicarboxylic acid (0.500 g, 1.86 mmol) was refluxed for two hours in excess SOCl2 (12 ml, 0.168 mol) and a drop of DMF was added in catalytic amount. SOCl2 was then removed at a reduced pressure resulting in diacyl chloride as pale yellow residue to which was added K2CO3 (0.567 g, 4.11 mmol), 2-methoxy aniline (0.506 g,4.11 mmol) and TBAHSO4 in catalytic amount and 25 ml of freshly dry distilled acetonitrile. The contents were refluxed until TLC monitoring indicated completion of the reaction. The contents were filtered and the solvent was vacuum evaporated to yield crude yellow solid. Recrystallization of crude product from mixture of methanol and chloroform resulted in the formation of pure amide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With water; acetic acid for 2h; Heating; | |
56% | With hydrogenchloride In ethanol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With 3 A molecular sieve In dichloromethane for 20h; Ambient temperature; | |
In methanol at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In methanol for 16h; Ambient temperature; | |
39% | In methanol at 50℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In methanol for 16h; Ambient temperature; | |
40% | In methanol | General procedure for synthesisof 1,10-phenanthroline-2,9-dicarbaldehyde and diaminemacrocycles General procedure: This procedure was performed using a modified literaturemethod [15]. A solution of 1,10-phenanthroline-2,9-dicarbaldehyde(1 equivalent) in methanol (1.5 mL/mol) wasadded dropwise to a solution of diamine (1 equivalent),in methanol (4.0 mL/mol) at ~ 0.40 mL/minute. The reactionmixture was stirred overnight, and a precipitate isformed. The precipitate was collected on a glass frit andwas washed with additional cold methanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol for 6h; Reflux; | |
60.1% | In ethanol for 6h; Reflux; | |
57% | In ethanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In methanol at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; magnesium chloride In methanol for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In chloroform for 2h; Heating; | |
With magnesium chloride In methanol at 25℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Stage #1: L-valine; 1,10-phenanthroline-2,9-dicarboxaldehyde With sodium hydroxide at 20℃; for 15h; Stage #2: With sodium tetrahydroborate In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | Stage #1: L-isoleucine; 1,10-phenanthroline-2,9-dicarboxaldehyde With sodium hydroxide at 20℃; for 15h; Stage #2: With sodium tetrahydroborate In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: L-methionine; 1,10-phenanthroline-2,9-dicarboxaldehyde With sodium hydroxide at 20℃; for 15h; Stage #2: With sodium tetrahydroborate In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: L-Aspartic acid; 1,10-phenanthroline-2,9-dicarboxaldehyde With sodium hydroxide at 20℃; for 15h; Stage #2: With sodium tetrahydroborate In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: L-glutamic acid; 1,10-phenanthroline-2,9-dicarboxaldehyde With sodium hydroxide at 20℃; for 15h; Stage #2: With sodium tetrahydroborate In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | Stage #1: L-phenylalanine; 1,10-phenanthroline-2,9-dicarboxaldehyde With sodium hydroxide at 20℃; for 15h; Stage #2: With sodium tetrahydroborate In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Stage #1: 1,10-phenanthroline-2,9-dicarboxaldehyde; rac-Ala-OH With sodium hydroxide at 20℃; for 15h; Stage #2: With sodium tetrahydroborate In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 1,10-phenanthroline-2,9-dicarboxaldehyde; L-histidine With sodium hydroxide at 20℃; for 15h; Stage #2: With sodium tetrahydroborate In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 20℃; for 12h; | ||
In ethanol for 4h; Reflux; | 2.3 Synthesis of 2,9-di(ethylaminomethyl)-1,10-phenanthroline trihydrochloride (H3LCl3) 2,9-Diformyl-1,10-phenanthroline (2 mmol, 0.54 g) was suspended in 50 ml of dry 12 EtOH, and 4 mmol of 13 ethylamine (0.120 ml) was added, the formed solution was kept under reflux and stirred for 4 h. Solid 14 NaBH4 (8 mmol, 0.30 g) was added to the reaction mixture in small portions. The above solution had been stirred for 12 h, and it was concentrated until a pale yellow solid appeared. The residue was dissolved in 25 ml 15 water and extracted three times with 15 ml CHCl3. The organic extract was concentrated to yield a yellow oil. The oil was dissolved in 5 ml EtOH and 16 conc. hydrochloric acid was added (2 mmol, 0.165 ml). The resulting yellow solid was filtered and washed with a small portion of EtOH. Final recrystallization of the product was carried out from 17 MeOH and filtered through an activated charcoal bed resulting in a white 18 powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With acetic acid In ethanol for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With TEA In methanol; dichloromethane at 20℃; for 96h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 430 mg / aq. HNO3 / 2 h / Heating 2: 89 percent / EDCI / HOAt / dimethylformamide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 430 mg / aq. HNO3 / 2 h / Heating 2: 89 percent / EDCI / HOAt / dimethylformamide / 1 h / 20 °C 3: 50 percent / 1,2-dichloro-ethane / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 430 mg / aq. HNO3 / 2 h / Heating 2: EDCI / HOAt / dimethylformamide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 430 mg / aq. HNO3 / 2 h / Heating 2: EDCI / HOAt / dimethylformamide / 1 h / 20 °C 3: 1,2-dichloro-ethane / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: CHCl3; methanol 2: NaBH4 / CHCl3; methanol / 24 h / 20 °C | ||
Multi-step reaction with 2 steps 1: CHCl3; methanol 2: sodium borohydride / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: CHCl3; methanol 2: NaBH4 / CHCl3; methanol / 24 h / 20 °C 3: 1.2 g / HBr; PhOH / acetic acid / 18 h / 90 °C | ||
Multi-step reaction with 3 steps 1: CHCl3; methanol 2: sodium borohydride / 24 h / 20 °C 3: 1.2 g / HBr; acetic acid; phenol / 18 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N, MgCl2 / methanol / 18 h 2: NaBH4 / methanol / 15 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / 60percent nitric acid / 4 h / Heating 2: SOCl2 / toluene | ||
Multi-step reaction with 2 steps 1: nitric acid / 3 h / Reflux 2: thionyl chloride / 3 h / Reflux; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: nitric acid 2: thionyl chloride / N,N-dimethyl-formamide / 2 h / Reflux |
Multi-step reaction with 2 steps 1: nitric acid / 3 h / Reflux 2: thionyl chloride / 3 h / 85 °C | ||
Multi-step reaction with 2 steps 1: nitric acid / 24 h / Reflux 2: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 24 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 2 steps 1: nitric acid / Reflux 2: thionyl chloride / 4 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | Stage #1: 1,10-phenanthroline-2,9-dicarboxaldehyde With hydroxylamine hydrochloride; triethylamine In acetonitrile for 3h; Reflux; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride In acetonitrile for 24h; Reflux; | |
Multi-step reaction with 2 steps 1: NH2OH*HCl / pyridine; ethanol / 2 h / Heating 2: 75 percent / acetic anhydride / 2 h / Heating | ||
Multi-step reaction with 2 steps 1: pyridine; hydroxylamine hydrochloride / ethanol / 2 h / Reflux 2: acetic anhydride / 2 h / Reflux |
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; triethylamine / acetonitrile / 4 h / Reflux 2: p-toluenesulfonyl chloride; pyridine / acetonitrile / 24 h / Reflux | ||
Multi-step reaction with 2 steps 1: triethylamine; hydroxylamine hydrochloride / acetonitrile 2: p-toluenesulfonyl chloride; pyridine / acetonitrile | ||
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; triethylamine / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride / Heating; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; triethylamine / acetonitrile / 4 h / Heating 2: p-toluenesulfonyl chloride; pyridine / acetonitrile / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In acetonitrile at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With p-toluolesulfonic acid In benzene p-toluenesulfonic acid in catalytic amount, refluxing benzene; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NaHCO3 In not given (N2 or Ar); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With NaHCO3 In water (Ar or N2); a flask charged with 1,10-phenanthroline-2,9-dicarboxaldehyde, sulfanilic acid, Cu2O, NaHCO3, sealed, purified of O2, H2O added, sealed, stirred at room temp.; evapd. (vac.); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NaHCO3 In water-d2 (Ar); for hours; not isolated, detected by NMR; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With NaHCO3 In water (Ar or N2); a flask charged with 1,10-phenanthroline-2,9-dicarboxaldehyde, sulfanilic acid, Cu2O, NaHCO3, sealed, purified of O2, H2O added, sealed, stirred overnight at room temp.; evapd. (vac.); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfanilamide In dimethylsulfoxide-d6 into an NMR tube were loaded amino-compounds followed by DMSO-d6, the tube's atm. was purged of O2 with three evacuation/argon purge cycles, Cu-complex was added, again purged with O2, left for 6 h at 50°C, (CH3)2NC6H4NH2 was added; detected by spectra; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.7% | In water under Ar atm. (+-)-1-amino-2,3-propanediol, 2,9-diformyl-1,10-phenanthroline and Cu complex in water were heated at 50°C overnight and kept at room temp. for 2 weeks; supernatant was removed, kept for 5 days; powder was dried under vac.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 20℃; | ||
In methanol | General procedure for synthesisof 1,10-phenanthroline-2,9-dicarbaldehyde and diaminemacrocycles General procedure: This procedure was performed using a modified literaturemethod [15]. A solution of 1,10-phenanthroline-2,9-dicarbaldehyde(1 equivalent) in methanol (1.5 mL/mol) wasadded dropwise to a solution of diamine (1 equivalent),in methanol (4.0 mL/mol) at ~ 0.40 mL/minute. The reactionmixture was stirred overnight, and a precipitate isformed. The precipitate was collected on a glass frit andwas washed with additional cold methanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With piperidine In ethanol at 20 - 40℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With trifluoroacetic acid at 20℃; for 0.333333h; Inert atmosphere; | |
65% | With trifluoroacetic acid at 20℃; for 0.333333h; Inert atmosphere; | 4.2 Bis(dipyrromethane) (5) To a solution of dialdehyde 1 (0.48g, 2.0mmol) in TFA (20mL), benzyl pyrrole ester 3 (2.1g, 8.2mmol) was added and the mixture stirred at 20°C for 20min under N2. The reaction mixture was poured onto ice and water (100mL), neutralized with 2.5M NaOH, and extracted with CHCl3 (3×20mL). The combined organics were dried (Na2SO4), rotary evaporated and the crude residue redissolved in the minimum amount of CHCl3. Precipitation upon the addition of EtOAc followed by filtration and drying under vacuum gave bis(dipyrromethane) 5 (1.6g, 65%) as a pale yellow solid: Rf 0.15 (hexanes/Et2O 1:1); mp 193°C; IR (film) νmax 3303, 1677, 1436, 1249cm-1; 1H NMR (CDCl3, 300MHz) δ 0.98 (t, J=7.4Hz, 12H), 1.06 (t, J=7.3Hz, 12H), 2.51 (q, J=7.4Hz, 8H), 2.66 (q, J=7.3Hz, 8H), 4.93 (s, 8H), 6.13 (s, 2H), 7.08 (m, 20H), 7.63 (d, J=8.3Hz, 2H), 7.72 (s, 2H), 8.19 (d, J=8.3Hz, 2H), 10.69 (s, 4H); 13C NMR (CDCl3, 75MHz) δ 16.4, 17.9, 18.9, 42.6, 65.7, 118.0, 123.5, 124.0, 126.6, 127.9, 128.1, 128.2, 128.5, 131.6, 134.0, 137.0, 138.3, 144.9, 160.2, 161.3; MS (FAB) m/z 1228 [M-H]+; HRMS (FAB) calcd for C78H81N6O8: [M+H]+ 1229.6116, found [M+H]+ 1229.6148. Anal. Calcd for C78H80N6O8: C, 76.20; H, 6.56; N, 6.84. Found: C, 76.42; H, 6.31; N, 6.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In methanol at 110℃; for 0.283333h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol at 110℃; for 0.283333h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 6-(2′-aminoethyl)-3,6,9-triaza-1(2,6)-pyridinacyclodecaphane; 1,10-phenanthroline-2,9-dicarboxaldehyde In ethanol at 20℃; for 2h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 2h; | ||
With sodium tetrahydroborate In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With piperidine In ethanol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine; hydroxylamine hydrochloride / ethanol / 2 h / Reflux 2: acetic anhydride / 2 h / Reflux 3: hydrazine hydrate / ethanol / 336 h / 20 °C | ||
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; triethylamine / acetonitrile / 4 h / Reflux 2: p-toluenesulfonyl chloride; pyridine / acetonitrile / 24 h / Reflux 3: hydrazine hydrate / ethanol / 144 h / 20 °C | ||
Multi-step reaction with 3 steps 1: triethylamine; hydroxylamine hydrochloride / acetonitrile 2: p-toluenesulfonyl chloride; pyridine / acetonitrile 3: hydrazine hydrate / ethanol |
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; triethylamine / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride / Heating; Inert atmosphere 3: hydrazine hydrate / ethanol / 16 h / 0 - 40 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: triethylamine; hydroxylamine hydrochloride / 4 h / Reflux 1.2: 32 h / Reflux 2.1: hydrazine hydrate / ethanol / 240 h / Reflux | ||
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; triethylamine / acetonitrile / 4 h / Heating 2: p-toluenesulfonyl chloride; pyridine / acetonitrile / 24 h / Heating 3: hydrazine hydrate / ethanol / 144 h / 20 °C | ||
Multi-step reaction with 2 steps 1.1: triethylamine; hydroxylamine hydrochloride / acetonitrile / 3 h / Reflux 1.2: 24 h / Reflux 2.1: hydrazine hydrate / ethanol / 336 - 360 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In ethanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In ethanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In acetonitrile at 65℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride; triethylamine / acetonitrile / 4 h / Reflux 2: p-toluenesulfonyl chloride; pyridine / acetonitrile / 24 h / Reflux 3: hydrazine hydrate / ethanol / 144 h / 20 °C 4: triethylamine / 1,4-dioxane / 72 h / Reflux | ||
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride; triethylamine / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride / Heating; Inert atmosphere 3: hydrazine hydrate / ethanol / 16 h / 0 - 40 °C / Inert atmosphere 4: 1-methyl-pyrrolidin-2-one / 16 h / 78 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: triethylamine; hydroxylamine hydrochloride / acetonitrile / 3 h / Reflux 1.2: 24 h / Reflux 2.1: hydrazine hydrate / ethanol / 336 - 360 h / 20 °C 3.1: triethylamine / 1,4-dioxane / 72 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With hydrazine hydrate In ethanol for 8h; Reflux; | 2,9-Dimethylenehydrazine-1,10-phenanthroline. 1,10-Phenanthroline-2,9-dicarbaldehyde (1 mmol,236 mg) in dry ethanol (15 mL) was added to the ethanol (30 mL) solution containing hydrazine hydrate(80%, 0.5 mL) under stirring. Then the mixture was heated under refluxing for 8 h and the yellow precipitate was separated by filtration. The solid was washed with diethyl ether and dried under vacuum. Yield: 81%. |
81% | With hydrazine In ethanol for 8h; Reflux; | 2,9-Dimethylenehydrazine-1,10-phenanthroline 1, 10-Phenanthroline-2,9- dicarbaldehyde (1 mmol, 236 mg) in dry ethanol (15 mL) was added to the dry ethanol (30 mL)containing hydrazine hydrate (80%, 0.5 mL) under stirring.Then the mixture was heated under refuxing for 8 hand the yellow precipitate was separated by fltration. Thesolid was washed with diethyl ether and dried under vacuum.Yield: 81%. mp: 279.0-281.0 °C. 1H NMR (400MHz, DMSO-d6, 298 K) δ 9.52 (s, 4H, NH2), 8.49 (d, 2H,phen-H), 8.02 (d, 2H, phen-H), 7.67(d, 2H, phen-H), 7.53(s, 2H, CH). Elemental analysis: Calc. for C14H12N6: C,63.62; H, 4.58; N, 31.80; Found: C, 63.93; H, 4.36; N,31.57. ESI-MS (m/z): 263.31 (M-H)-. |
75% | With hydrazine hydrate In methanol at 20℃; for 20h; | To a solution of 1,10-phenanthroline-2,9-dicarbaldehyde1(2.1 g, 9 mmol) in 150 ml of methanol, 6 equivalents of NH2NH2·H2O (54.1 mmol, 2.66 ml) were added whilst maintaining stirring at room temperature for 20 hours. Reaction mixture was filtrated and the filtrate was evaporated giving the hydrazone intermediate (1.8 g, 6.75 mmol). The hydrazone intermediate was dissolved in 100 ml of CHCl3 and 8 equivalents of MnO2 (5.5g, 54 mmol) were added. Reaction mixture was heated at reflux during 24 hours. The mixture was then filtrated with celite, washing with dichloromethane, andthe combined filtrates were evaporated. Finally precipitation of the crude with diethylether afforded compound 1 (1.4g, 5.4 mmol).1H NMR (300 MHz, DMSO) δ = 8.46 (s, 2H), 8.35 (s, 2 H), 8.21 (d, J = 9.2 Hz, 2 H), 8.04 (d, J = 9.2 Hz, 2 H). 13C NMR (75MHz, DMSO) δ = 138.01, 133.15, 127.56, 126.58, 126.25, 120.33, 117.58. IR (neat,cm-1) 3126, 3061, 1585, 1435, 1379, 1243, 1102, 960, 849, 833, 774, 677. HRMS foundfor [M+H]+ 261.0881; C14H9N6 requires 261.0883. MS (E.I.): m/z (%) 205.0763 (41),176.0625 (100), 151.0542 (38). UV λmax (nm) (log ε) (DMSO) 260 (4.31), 265 (4.31),276 (4.31), 318 (3.9), 333 (3.9), 351 (4.0), 370 (3.9), 401 (3.0). Fluorescence emissionλmax (nm) (DMSO) λexc= 286, λem= 331 and 390. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In isopropyl alcohol at 65℃; for 20h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In methanol at 20℃; for 7h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In dichloromethane at 20℃; for 27h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In methanol; ethanol; chloroform at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol Reflux; | Macrocyclic Schiff base complexes 2,2’-Bipyridine-6,6’-dicarboxaldehyde or 1,10-phenanthroline-2,9-dicarboxaldehyde(1.0 mmol) was dissolved in MeOH (25 mL)containing Pb(ClO4)2·H2O or Pb(NO3)2 (1.0 mmol). The solution was stirred vigorously and heated while a methanolic solution of 6,6’-bis(2-aminophenoxymethyl)-2,2’-bipyridine(0.40 g, 1.0 mmol) was added slowly. The resultant solution was refluxed for 4-5 h and filtered hot. The solvent of the reaction mixture was reduced to half its original volume andthen the mixture was placed in a refrigerator to induce precipitation.The yellow powder products were filtered and dried.Yields 70 and 50 % respectively |
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 |
---|---|---|
30% | With iodine In acetonitrile at 20℃; for 8h; | General method for synthesis of Tetraindoles General procedure: A round-bottomed flask (10 mL) was charged with dialdehyde (1.0 mmol),5-hydroxyindole (0.53 g, 4 mmol), and iodine (0.05 g, 0.2 mmol) in MeCN (5 mL).This mixture was then stirred at room temperature for 0.5 to 8 h. The reactionmixture was treated with aqueous Na2S2O3, andthe solution was extracted with ethyl acetate (3 × 20 mL). The combined organiclayers were dried over MgSO4 and filtered. The solvent wasremoved under reduced pressure, and the residue was subjected to columnchromatography (ethyl acetate/hexane, 1/1), followed by recrystallization |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol; at 50℃; for 48h; | 1,9-Diformyl-1,10-phenanthroline (0.001 mmol, 0.200 g) was dissolved in50 mL of CH3OH. To this methanolic solution,<strong>[22990-77-8]2-(aminomethyl)piperidine</strong> (0.002 mmol, 0.184 g) was addeddrop by drop. This reaction mixture was stirred continuouslyfor 48 h at 50 C. During this, the colour of the reactionmixture has changed to red-brown, indicating the formationof Schiff base. The solvent was removed under vacuum andthe resultant orange-red powder was isolated. Yield. 70 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In ethanol; dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: bromopentene With iodine; magnesium In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux; Stage #2: 1,10-phenanthroline-2,9-dicarboxaldehyde Inert atmosphere; Reflux; | bis-Alkene dione 3 Mg turnings (139 mg, 5.79 mmol) and iodine in THF (5 mL) were heated to reflux until the brown colordisappeared. Then, 5-bromo-1-pentene (273 mg, 1.92 mmol) was added and mixture was stirred for 30min. Next, 1,10-phenanthroline-2,9-dicarbaldehyde (2; 100 mg, 0.42 mmol) was added and the resultingmixture was stirred and heated to reflux for 3 h. At the conclusion of reaction (TLC monitoring), 2 N HClwas added and reaction mixture was stirred for 30 min. The reaction mixture was diluted with EtOAc (10mL) and H2O (10 mL) and the reaction mixture was stirred well and extracted with EtOAc. The organiclayer was washed with brine and dried with Na2SO4. EtOAc was removed under reduced pressure and thecrude product obtained was purified by column chromatography to obtain the bis-alkene dione 3 (135 mg,86% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In acetonitrile Reflux; | General procedure for the synthesis of Schiff bases and hemiaminals: (Schemes 1-4) General procedure: General procedure for the synthesis of Schiff bases and hemiaminals: (Schemes 1-4) Each dicarboxaldehydes (1, 4, 7 & 10) were dissolved in refluxing solvent (EtOH, MeOH or CH3CN). 4-Amino-3,5-dimethyl-1,2,4-triazole was then added to the hot solutions of dicarboxaldehydes and refluxing was continued. After 2-4 h the reaction mixtures were cooled to room temperature to isolate the products as solid precipitate. The products were collected by vacuum filtration and washed with cold methanol followed by hot acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol Reflux; | General procedure for the synthesis of Schiff bases and hemiaminals: (Schemes 1-4) General procedure: General procedure for the synthesis of Schiff bases and hemiaminals: (Schemes 1-4) Each dicarboxaldehydes (1, 4, 7 & 10) were dissolved in refluxing solvent (EtOH, MeOH or CH3CN). 4-Amino-3,5-dimethyl-1,2,4-triazole was then added to the hot solutions of dicarboxaldehydes and refluxing was continued. After 2-4 h the reaction mixtures were cooled to room temperature to isolate the products as solid precipitate. The products were collected by vacuum filtration and washed with cold methanol followed by hot acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In methanol; chloroform for 10h; Reflux; | 4.4. Synthesis of chemosensor L Compound 2 (0.30g, 1.27mmol) was dissolved in 5ml drychloroform with continuous stirring and then 0.880g of uorescein hydrazide (2.54mmol) in 15ml dry methanolwas added to the solution and heated to reflux for 10h. A white precipitate was appeared. After that, the reactionmixture was cooled to room temperature and then theprecipitate was collected through filtration. The collected residue was washed several times with ethanol and dried in air to give white-coloured pure compound L in 90%(1.02g) yield; M.P.>250°C. 1H NMR (300MHz, DMSO-d6, J(Hz), δ (ppm)): 9.97 (4H, s, -OH), 9.07 (2H, s, -CH=N), 8.44(2H, d, J=8.4Hz), 7.99 (6H, m), 7.71-7.62 (4H, m), 7.17 (2H,d, J=7.6Hz), 6.84 (4H, d, J=2.0Hz), 6.61 (4H, d, J=8.4Hz),6.50 (4H, dd, J = 2.4 and 2.0 Hz). 13C NMR (75 MHz,DMSO-d6,) δ (ppm): 65.28, 79.17, 102.95, 109.65, 112.52,118.79, 123.79, 127.83, 128.91, 134.84, 137.49, 144.70,147.08, 151.14, 152.09, 153.41, 158.80, 164.32. IR (KBr pellet,cm-1): 1672, 1610, 1505, 1349, 1253. ESI-MS (positivemode, m/z) calculated for C54H32N6O8=892.2282. Found892.9075, 915.8401 [L+Na]+. Anal. Calcd for C54H32N6O8: C,72.64; H, 3.61; N, 9.41%. Found: C,72.53; H, 3.58; N, 9.44%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With potassium carbonate In methanol at 20℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | Stage #1: 4-<(diethylphosphono)methyl>pyridine With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 1,10-phenanthroline-2,9-dicarboxaldehyde for 24h; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With trifluoroacetic acid at 20℃; for 0.333333h; Inert atmosphere; | 4.3 Bis(dipyrromethane) (6) The same reaction as above with ethyl pyrrole ester 4 (1.6g, 8.2mmol), gave bis(dipyrromethane) 6 (1.3g, 66%) as a white solid: Rf 0.25 (hexanes/Et2O 1:1); mp 243°C; IR (film) νmax 3300, 1681, 1438, 1254cm-1; 1H NMR (CDCl3, 300MHz) δ 1.02 (t, J=7.4Hz, 12H), 1.09 (t, J=7.1Hz, 12H), 1.15 (t, J=7.4Hz, 12H), 2.56 (q, J=7.4Hz, 8H), 2.73 (q, J=7.4Hz, 8H), 4.04 (m, 8H), 6.16 (s, 2H), 7.65 (d, J=8.3Hz, 2H), 7.70 (s, 2H), 8.19 (d, J=8.3Hz, 2H), 10.75 (s, 4H); 13C NMR (CDCl3, 75MHz) δ 14.5, 16.2, 16.3, 17.9, 18.8, 42.4, 59.8, 118.0, 123.1, 124.0, 126.4, 127.9, 131.6, 133.6, 137.9, 144.9, 160.3, 161.6; MS (FAB) m/z 980 [M-H]+; HRMS (FAB) calcd for C58H72N6O8: [M+.] 980.5412, found [M+.] 980.5374. Anal. Calcd for C58H72N6O8: C, 70.99; H, 7.40; N, 8.56. Found: C, 70.62; H, 7.59; N, 8.61. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethanol Reflux; | Synthesis of probe L To a solution of 1,10-phenanthroline-2,9-dicarbaldehyde (0.10g, 0.42mmol) in ethanol (2mL) was added 1H-indole-2-carbohydrazide (0.16g, 1.83mmol). After the mixture was stirred under reflux for overnight, the products were cooled to room temperature. The precipitates were collected by filtration, followed by washing with ethanol (3×10mL), and then recrystallized from EtOH to give the desired product as a yellow powder (90%). M.p: 225°C; 1H NMR (300MHz, DMSO-d6) δ: 12.26 (s, 2H), 11.95 (s, 2H), 8.86 (s, 2H), 8.62 (d, J=8.4Hz, 2H), 8.42 (d, J=8.1Hz, 2H), 8.09 (s, 2H), 7.76 (d, J=7.2Hz, 2H), 7.52 (d, J=8.4Hz, 2H), 7.43 (s, 1H), 7.29 (t, J=7.5Hz, 2H), 7.13 (t, J=7.5Hz, 2H); 13C NMR (75.4MHz, DMSO-d6) δ: 153.50, 147.54, 144.97, 137.22, 137.04, 129.72, 128.97, 127.25, 126.97, 124.21, 121.95, 121.38, 120.12, 119.53, 112.49, 104.33; HRMS (EI): Calcd for C32H22N8O2 (M+), m/z 550.1866; found m/z 550.1867 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: [((2a1S,4a1R)-2a1,4a1-dimethyldecahydro-1H-2a,4a,7a,9a-tetraazacyclopenta-[cd]phenalen-1-yl)methyl]amine; 1,10-phenanthroline-2,9-dicarboxaldehyde In ethanol for 2h; Stage #2: With sodium tetrahydroborate; ethanol at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With acetic acid In ethanol for 2h; Reflux; | Synthesis of receptor 1 (1, 10-phenanthroline-2,9-dialdehyde bis-(-p-nitrophenylureasemi carbohydrazone)) Receptor 1 was synthesized according to the procedurereported (Scheme 1) (11). To the solution of 1, 10-phenanthroline-2, 9-dicarbaldehyde (236 mg, 1 mmol) in ethanol,p-nitro-phenylureasemi-carbazine (392 mg, 2 mmol)was added. After a catalytic amount of acetic acid wasadded, the resulting solution was refluxed for 2 h. Thenthe precipitate was filtered while it was still hot andwashed with hot ethanol for several times. Yellow solidwas obtained in 80% yield. 1H NMR (400 MHz, DMSO-d6),11.52 (s, J1 = 11.52 Hz, 2H, N-H), 9.72 (s, J1 = 9.72 Hz, 2H,N-H), 8.71 (dd, J1 = 8.69 Hz, J2 = 8.72 Hz, 2H, phenyl-H),8.53 (d, J1 = 8.51 Hz, 2H, phenyl-H), 8.35 (s, J1 = 8.35 Hz,2H, C-H), 8.20 (d, J1 = 8.19 Hz, 4H, phenyl-H), 7.99 (dd,J1 = 7.98 Hz, J2 = 8.01 Hz, 6H, phenyl-H) (Figure S1). 13CNMR (100 MHz, DMSO-d6), 165.96, 152.98, 152.27, 145.37,144.50, 142.56, 141.48, 136.17, 130.25, 128.54, 126.85,124.56, 119.11, 109.14 (Figure S2). IR (KBr): 3367 cm-1: vN-H,3300-3000 cm-1: vC-H, 1707 cm-1: vC=O, 1542 cm-1: vC=C,1505 cm-1: vC=N, 1330 cm-1: δC-H, 853 cm-1: δAr-H (Figure S3).M. P.: 284-286 °C. ESI-MS (m/z): calculated for C28H20N10O6[M]-: 591, found: 591. (Figure S4 (a)). Elemental analysiscalculated for C28H20N10O6: C, 56.76; H, 3.40; N, 23.64; found:C, 56.69; H, 3.36; N, 23.92. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.45 g | In methanol for 4h; Inert atmosphere; | 4.2. Synthesis of L1/D1 The synthesis of compoundsL1 and D1were showed inScheme 1. 1,10-Phenanthroline-2,9-dicarbaldehyde(0.27 g, 1.14 mmol) was dissolved in absolute CH3OH(10 mL) and excess mandelohydrazide (0.57 g,3.43 mmol) dissolved in absolute CH3OH was addedslowly under stirring conditions. The mixture was stirredon the oil-bath for 4h under N2 atmosphere until a whitesolid appeared. After cooled to room temperature, thewhite solid was separated and filtered. The crude productwas washed with absolute CH3OH several times and driedin air to give the products L1 and D1 as white solids. 1HNMR δ 12.11 (s, 2H), 8.86 (s, 2H), 8.51 (d, J = 8.0 Hz, 2H),8.30 (d, J = 8.0 Hz, 2H), 8.01 (s, 2H), 7.57(d, J = 4.0 Hz,4H),7.34-7.26 (m, 6H),6.63 (s, 2H),5.23 (s, 2H); 13C NMRδ169.86, 154.12, 153.61,148.60, 145.36, 140.97, 137.56,129.41, 128.68, 128.27, 127.71, 127.11, 119.99, 74.15;HRMS: Calcd for: [M + H]+: 533.1932; Found: 533.1935;IR:3404, 3232,1640,1525,1491,1450, 1409,1104,858,698 cm-1; L1, 0.42, yield 68.85%, m.p. 201.3-202.2 °C,Specific rotation, α20D = + 128.56 (c = 0.01, DMSO); D1,0.45g, yield: 73.77%, m.p. 200.9-201.4°C. Specific rotationα20D = -130.07(c = 0.01, DMSO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol for 3h; Reflux; | 2.1. Synthesis of 1,10-Phenanthroline derivative The ethanolic solutions of 1,10-Phenanthroline-2,9-dicarbaldehyde,3-amino-7-nitronaphthalen-2-ol (20 mM) (10 mM) were thoroughlymixed in RB flask. Then, it was refluxed for 3 hrs. TLC plate has utilizeto monitor the progress of the reaction. The solid residue was separatedand dried in vacuum desiccator (Scheme 1).Ligand (H2L): Mol. Formula: C36H20N6O6, Mass: 600. Productivity:70%; Elemental composition: Calcd for; Nitrogen 13.81, Carbon 67.10,Hydrogen 3.31; Found: Nitrogen 13.68, Carbon 67.02, Hydrogen 3.20,UV (nm): 330, 248 nm. FT-IR (cm-1): 3320 (Aromatic OeH);3080-3078 (AreH); 2960, 2886 (CeH); 1650 (azomethine, C]N);1232 (Aromatic CeOH). 1H NMR (ppm): 8.8 (HC]N, 2H, s), 11.2(eOH, 2H, s), 6.8-7.9 (16H, m). FAB-MS: 601. 13C NMR (ppm)(DMSOWd6) = 108.36, 125.5, 128.6, 130.06, 135.58, 152.18,160.40 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.25% | In ethanol at 55℃; for 6h; | 2.2.3. Synthesis of Lpov Lpov was synthesized using the one-pot method. 2-[O-(1-Ethyloxyamide)]oxime-6-methoxyphenol (453 mg, 2.0 mmol) and 1,10-phenanthroline-2,9-dicarboxaldehyde (236 mg, 1.0 mmol) were dissolvedin the ethanol (20 mL), respectively. The reaction was stirred at 55 for6 h. At the end of the reaction, a large amount of yellowish precipitate isgenerated at the bottom of the round bottom flask. The product is filterdried.Light yellow solid: 517.23 mg. M.p.: 145-148 C. Yield: 79.25%.Anal. calcd. for C34H32N6O8 (%): C, 62.57; H, 4.94; N, 12.88. Found: C,62.82; H, 4.75; N, 12.67. 1H NMR (500 MHz, DMSO) δ 9.41 (s , 2H), 8.52(dd, J = 18.5, 15.5 Hz, 6H), 8.19 (d, J = 8.4 Hz, 2H), 8.06 (s, 2H), 7.17(d, J = 7.9 Hz, 2H), 7.00 (d, J = 9.1 Hz, 2H), 6.81 (t, J = 8.0 Hz, 2H),4.55 (dd , J = 5.7, 2.9 Hz, 4H), 4.48 (dd, J = 5.6, 3.0 Hz, 4H), 3.80 (s,6H). |
Tags: 57709-62-3 synthesis path| 57709-62-3 SDS| 57709-62-3 COA| 57709-62-3 purity| 57709-62-3 application| 57709-62-3 NMR| 57709-62-3 COA| 57709-62-3 structure
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