CN104910076A - Preparation for bis-benzimidazolium salts and applications in intramolecular coupling reaction - Google Patents
Preparation for bis-benzimidazolium salts and applications in intramolecular coupling reaction Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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Abstract
The invention discloses preparation for bis-benzimidazolium salts and applications in an intramolecular coupling reaction, and relates to a preparation method for bis-benzimidazolium salts through bridging of diphenol and a palladium catalysis C-C coupling reaction. Benzimidazole, 2,2'-diphenol, chloroethanol, thionyl chloride and the like are employed as raw materials and bis-benzimidazolium ligands are synthesized. The ligands are subjected to catalysis by utilization of metal salts of palladium and intramolecular C-C coupling compounds are obtained. Research of the intramolecular coupling reaction of the bis-benzimidazolium salts under catalysis of metal palladium is expected. The preparation has advantages of concise preparation and obvious catalysis effects, can be used for synthesis of benzimidazole-containg biaryl units, and is hopeful to be applied in the intramolecular coupling catalysis field.
Description
About the statement subsidizing research or exploitation
The present invention is state natural sciences fund (fund number is 21172172), Tianjin Natural Science Fund In The Light (fund number is 11JCZDJC22000), Tianjin innovation team of institution of higher education training plan (fund number is TD12-5038) and Tianjin Normal University's research for application and development fund (fund number: 52XK1202) carry out under subsidizing.
Technical field
The invention belongs to organic synthesis and Molecular modelling technical field, relate to the synthesis of the bis-benzimidazole salt of xenol bridging, and C-C linked reaction in its molecule occurred under the catalysis of palladium salt.As the research of C-C linked reaction in the preparation method of precursor and its molecule in particular containing the bisbenzimidazole of xenol bridging.
Background technology
Linked reaction is by the process of two molecules by a reaction formation recruit.And to form new C-C be extremely important in organic chemistry.When the organic substance such as synthetic drugs, plastics, needing to link together carbon atom with little organic molecule builds new complicated macromole, and the method thus connecting C-C in organic synthesis is efficiently the important tool in Synthetic Organic Chemistry.Because carbon atom chemical property torpescence, not easily be combined with each other between carbon atom, relate to the chemical reaction between two carbon atoms, conditional request just can be harsher.Along with further deep to the research of organic synthesis, 20 th century later, scientists finds a large amount of by the transition metal-catalyzed reaction creating new organic molecule, impels Synthetic Organic Chemistry fast-developing.
As everyone knows, transition metal-catalyzed C-C linked reaction is widely used in organic synthesis and industry.In numerous catalyzer, the catalyzer based on palladium metal is building C-C key, plays important role in C-N key and other C-heteroatomic bonds.The cross-coupling reaction of palladium chtalyst is one of the most efficient method, and is widely used in synthesis biaryl unit.Palladium catalysed cross coupling reaction is at the study on the synthesis of natural product, and the aspects such as pharmaceutical industry and type material synthesis are all widely used.Existing lot of documents reports and uses palladium catalysed cross coupling reaction synthesising macromolecule copolymer, functional complicated molecule etc. at present.Benzoglioxaline salt because it is at Organic Light Emitting Diode, ionic liquid, fluorescence identifying, the application in the field such as battery and cell and receiving much concern.
Summary of the invention
The object of the present invention is to provide by the bisbenzimidazole of the xenol bridging intramolecular coupling compound as precursor.
The present invention also relates to the method preparing this type of intramolecular coupling compound precursor.
The present invention relate to again the method for this type of intramolecular coupling compound of preparation simultaneously, and carries out crystallography sign to it.
What the present invention relates to the crystal of coupling compound in this quasi-molecule forms method, the research of take off data and data.
In molecule involved in the present invention, coupling compound is all that method by spreading or volatilize is cultivated and obtained.
In molecule in the present invention, coupling compound is all undertaken measuring and data characterization by x-ray diffractometer.
The bis-benzimidazole salt part that the present invention further discloses xenol bridging intramolecular coupling compound processed in application.
For completing above-mentioned every goal of the invention, technical solution of the present invention is as follows:
The invention discloses a kind of bis-benzimidazole salt part with xenol bridging, it has following structure:
The present invention further discloses the preparation method of described intramolecular coupling compound, it is characterized in that:
(1) in organic solvent 2,2 '-xenol, salt of wormwood are stirred 0.5 h under nitrogen protection 50 C, then slowly drip chloroethanol; Mixing solutions to react 24 h at 110 C, and aftertreatment obtains 2, the white solid of 2 '-bis-(2-hydroxyethyl) biphenyl;
(2) in organic solvent 2,2 '-bis-(2-hydroxyethyl) biphenyl and pyridine are uniformly mixed, then slowly drip thionyl chloride; Mixing solutions to react 6 h at 70 C, and aftertreatment obtains 2, the light yellow solid of 2 '-bis-(2-chloroethoxy) biphenyl;
(3) by 2, the tetrahydrofuran solution of 2 '-bis-(2-chloroethoxy) biphenyl at room temperature stirs 10-20 min, add NaI and the tetrahydrofuran solution containing N-ethyl benzo imidazole, this mixing solutions stirs 5 days adularescent throw outs and generates under 60-70 C, 2 are obtained, the white solid of 2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl salt compounded of iodine after aftertreatment; To 2, the methanol solution of ammonium hexafluorophosphate is added in the methanol solution of 2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl salt compounded of iodine, adularescent Precipitation, 2 are obtained after aftertreatment, 2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl hexafluorophosphate (
1);
Wherein 2,2 ' xenol in step (1): salt of wormwood: the mol ratio of chloroethanol is 1:4:4.
2,2 '-bis-(2-hydroxyethyl) biphenyl in step (2): pyridine: the mol ratio of thionyl chloride is 1:5:5.
2,2 '-bis-(2-hydroxyethyl) biphenyl in step (3): N-ethyl benzo imidazole: NaI: the mol ratio of ammonium hexafluorophosphate is 1:1.3:1.6:1.6.
Described organic solvent is selected from the mixture of one or more in tetrahydrofuran (THF), methylene dichloride, trichloromethane, anhydrous diethyl ether, acetonitrile, anhydrous methanol, DMF.
The present invention further disclose have by the bis-benzimidazole salt part of xenol bridging intramolecular coupling compound processed in application.Experiment proves: by the bis-benzimidazole salt part of xenol bridging, C-C linked reaction in molecule can occur under the metal salt catalyst of palladium.
In the present invention, crystal data and structure refinement parameter are included in supportive information.Bruker SMART 1000 CCD diffractometer carries out, and experimental temperature is 113 (2) K, under 50kV and 20mA, with Mo-K α radiation (0.71073) operation, carries out data gathering and reduction with SMART and SAINT software,
θscope be 1.8 <
θ< 25o.Application SADABS program carries out empirical absorption rectification.Crystalline structure is solved by direct method, carries out complete matrix least-squares refinement with SHELXTL bag to whole non-hydrogen atom coordinate anisotropy thermal parameter.
The crystalline structure figure of the coupling compound that application example 1 obtains is shown in Figure of description 1.
Accompanying drawing illustrates:
The intramolecular coupling compound crystal structure iron of Fig. 1 obtained by application example 1.
Embodiment
In order to simple and clearly object, the hereafter appropriate description eliminating known technology, in order to avoid the description of those unnecessary details impact to the technical program.Below in conjunction with preferred embodiment, the present invention will be further described, and what be illustrated especially is, prepare the initial substance N-ethyl benzo imidazole of the compounds of this invention, 2,2 ' xenol, chloroethanol, sulfur oxychloride etc. all can commercially or easily be obtained by known method.
The reagent prepared used by the compounds of this invention all derives from Tianjin unit and stands and Ke Wei Chemical Co., Ltd., and rank is analytical pure.
Need in addition to be illustrated: all experimental implementation solvent used is through normal process purifying.All for the synthesis of being all analytical pure with the reagent analyzed, not through further process.Fusing point is measured by Boetius block apparatus.
1h NMR composes by mercury variable V x400 spectrophotometer record, and surveying range is 400 MHz and 100 MHz respectively.Chemical shift, δ, the TMS with reference to international standard measures.Ultimate analysis is measured by Perkin-Elmer 2400C elemental analyser.
Embodiment 1 (
1)
By 2; 2 '-xenol (1.000 g; 5.4 mmol) join N; salt of wormwood (2.980 g of dinethylformamide (150ml); 21.6 mmol) in suspension liquid; under nitrogen protection, 50 C drip chloroethanol (1.740 g, 21.6 mmol) after stirring 0.5 h, and after dropwising, 110 C stir 24 h.Deep yellow solution is obtained after filtration.400 ml water are added, with dichloromethane extraction (30 mL × 3) in filtrate.Extraction liquid anhydrous magnesium sulfate drying.2 are obtained, the white solid of 2 '-bis-(2-hydroxyethyl) biphenyl after removing methylene dichloride.Productive rate: 1.296 g (87%).Fusing point: 42-44 C.
1H NMR (400 MHz, CDCl
3): δ 7.36 (t, J = 7.8 Hz, 2H, PhH), 7.26 (q, J = 2.9 Hz, 2H, PhH), 7.10 (t, J = 7.4 Hz, 2H, PhH), 7.02 (d, J = 8.0 Hz, 2H, PhH), 4.05 (t, J = 4.2 Hz, 4H, CH
2), 3.72 (t, J = 4.4 Hz, 4H, CH
2), 2.80 (s, 2H, OH).
13C NMR (100 MHz, CDCl
3): δ 155.8, 131.3, 129.0, 122.1 and 114.1 (PhC), 71.5 (OCH
2CH
2), 61.1 (OCH
2CH
2).
Thionyl chloride (2.170 g, 18.2 mmol) is dripped in the chloroform soln of 2,2 '-bis-(2-hydroxyethyl) biphenyl (1.000 g, 3.65 mmol) and pyridine (1.440 g, 18.2 mmol).Mixing solutions stirs 6 h at 70 C.Add 300 ml water after completion of the reaction wherein, separatory obtains trichloromethane layer, uses anhydrous magnesium sulfate drying.Removing trichloromethane obtains 2, the light yellow solid of 2 '-bis-(2-chloroethoxy) biphenyl.Productive rate: 0.738 g (65%).Fusing point: 52-54 C.
1H NMR (400 MHz, CDCl
3): δ 7.31 (m, 2H, PhH), 7.28 (m, 2H, PhH), 7.06 (t, J = 7.4 Hz, 2H, PhH), 6.96 (d, J = 8.0 Hz, 2H, PhH), 4.18 (t, J = 6.2 Hz, 4H, CH
2), 3.65 (t, J = 6.2 Hz, 4H, CH
2).
13C NMR (100 MHz, CDCl
3): δ 155.6, 131.8, 128.2, 121.2 and 112.7(PhC), 68.7 (OCH
2CH
2), 41.8 (OCH
2CH
2).
N-ethyl benzo imidazole (1.690 g are added in 100 ml tetrahydrofuran (THF)s, 11.6 mmol), 2,2 '-bis-(2-chloroethoxy) biphenyl (1.500 g, 8.9 mmol) and sodium iodide (2.170 g, 14.5 mmol) return stirring 5 days.Adularescent Precipitation.Bis-benzimidazole salt 2 is obtained with a small amount of tetrahydrofuran (THF) drip washing, the white solid of 2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl salt compounded of iodine after suction filtration.Ammonium hexafluorophosphate (2.360 g, 14.5 mmol) is added, adularescent Precipitation immediately in the methanol solution of 100 ml 2,2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl salt compounded of iodine.2 are obtained with a small amount of methyl alcohol drip washing, 2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl hexafluorophosphate after suction filtration.Productive rate: 2.417 g (61%).Fusing point: 104-106 C.
Anal. Calc. For C
34H
36N
4O
2P
2F
12: C, 49.64; H, 4.41; N, 6.81. Found: C, 49.53; H, 4.25; N, 6.62.
1H NMR (400 MHz, DMSO-d
6): δ 9.33 (s, 2H, 2-bimiH), δ 8.02 (d, J = 7.6 Hz, 2H, PhH), 7.64 (t, J = 6.8 Hz, 2H, PhH), 7.55 (d, J = 8.0 Hz, 2H, PhH), 7.45 (d, J = 6.8 Hz, 2H, PhH), 7.32 (d, J = 1.6 Hz, 2H, PhH), 6.98 (d, J = 8.0 Hz, 2H, PhH), 6.86 (s, 4H, PhH), 4.68 (s, 4H, CH
2), 4.41 (d, J = 6.4 Hz, 4H, CH
2). 4.26 (s, 4H, CH
2), 1.45 (s, 6H, CH
3).
13C NMR (100 MHz, DMSO-d
6): δ 154.6 (PhC), 141.7 (bimi-NCN), 131.1, 130.7, 130.5, 128.7, 126.4, 126.2, 120.9, 113.5, 113.4 and 112.5 (PhC), 65.7 (OCH
2CH
2), 48.5 (OCH
2CH
2), 42.1 (CH
2CH
3), 13.9 (CH
3) (bimi = benzimidazole).
Its experiment flow is shown below:
Application example 1
Sodium-acetate (0.199 g, 2.4 mmol) is added in 10 ml acetonitriles and 10 ml methylene dichloride, palladium (0.080 g, 0.36 mmol) and part (
1) (0.200 g, 0.2 mmol), under nitrogen protection, 50 C stir 24 h.Filtration obtains filtrate, and filtrate is placed in ether slowly to be spread, after two weeks test tube wall grow applicable X-ray single crystal diffraction test yellow transparent bulk crystals (
2).Productive rate: 0.083 g (38%), fusing point: 192-194 C.Anal. Calc. for C
38H
38F
12N
6O
2P
2: C, 50.67; H, 4.25; N, 9.33. Found: C, 49.95; H, 3.87; N, 6.96.
1H NMR (400 MHz, DMSO-d
6): δ 8.26 (m, 4H, PhH), 8.02 (t, J = 7.6 Hz, 4H, PhH), 7.80 (m, 4H, PhH), 7.75 (t, J = 7.8 Hz, 2H, PhH), 4.80 (t, J = 5.4 Hz, 4H, CH
2) 4.72 (q, J = 7.2 Hz, 4H, CH
2), 4.64 (t, J = 5.6 Hz, 4H, CH
2), 1.60 (t, J = 7.2 Hz, 6H, CH
3).
13C NMR (100 MHz, DMSO-d
6): δ 151.0 (bimi-NCN), 146.0, 135.3, 130.8, 129.6, 128.9, 125.2, 123.5, 116.4, 115.1, 112.2 and 111.4 (PhC), 74.6 (OCH
2CH
2), 41.0 (OCH
2CH
2), 40.0 (CH
2CH
3), 12.8 (CH
3).
Its experiment flow is as follows:
Crystalline structure is shown in Figure of description 1.
Intramolecular coupling compound crystal structural parameter prepared by application example 1
In sum, content of the present invention is not limited in instances, and the knowledgeable people in same area can propose other example easily within technical director's thought of the present invention, but this example all comprises within the scope of the present invention.
Claims (4)
1. have the bis-benzimidazole salt part by xenol bridging, its structure is as follows:
。
2. the preparation method of the bis-benzimidazole salt part of xenol bridging described in claim 1, is characterized in that:
(1) in organic solvent 2,2 '-xenol, salt of wormwood are stirred 0.5 h under nitrogen protection 50 C, then slowly drip chloroethanol; Mixing solutions to react 24 h at 110 C, and aftertreatment obtains 2, the white solid of 2 '-bis-(2-hydroxyethyl) biphenyl;
(2) in organic solvent 2,2 '-bis-(2-hydroxyethyl) biphenyl and pyridine are uniformly mixed, then slowly drip thionyl chloride; Mixing solutions to react 6 h at 70 C, and aftertreatment obtains 2, the light yellow solid of 2 '-bis-(2-chloroethoxy) biphenyl;
(3) by 2, the tetrahydrofuran solution of 2 '-bis-(2-chloroethoxy) biphenyl at room temperature stirs 10-20 min, add NaI and the tetrahydrofuran solution containing N-ethyl benzo imidazole, this mixing solutions stirs 5 days adularescent throw outs and generates under 60-70 C, 2 are obtained, the white solid of 2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl salt compounded of iodine after aftertreatment; To 2, the methanol solution of ammonium hexafluorophosphate is added in the methanol solution of 2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl salt compounded of iodine, adularescent Precipitation, 2 are obtained after aftertreatment, 2 '-bis-[2-(N-ethyl benzo imidazole base) oxyethyl group] biphenyl hexafluorophosphate (
1);
Wherein 2,2 ' xenol in step (1): salt of wormwood: the mol ratio of chloroethanol is 1:4:4;
2,2 '-bis-(2-hydroxyethyl) biphenyl in step (2): pyridine: the mol ratio of thionyl chloride is 1:5:5;
2,2 '-bis-(2-hydroxyethyl) biphenyl in step (3): N-ethyl benzo imidazole: NaI: the mol ratio of ammonium hexafluorophosphate is 1:1.3:1.6:1.6.
3. preparation method as claimed in claim 2, wherein said organic solvent is selected from the mixture of one or more in tetrahydrofuran (THF), methylene dichloride, trichloromethane, anhydrous diethyl ether, acetonitrile, anhydrous methanol, DMF.
4. the bis-benzimidazole salt part of xenol bridging described in claim 1 is in the application of intramolecular coupling compound in preparation in coupling compound, and the single crystal data of the intramolecular coupling compound prepared by it is:
。
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