CN110078737A - Perfluoroalkyl substituted benzimidazole and compound of isobioquin group and preparation method thereof - Google Patents
Perfluoroalkyl substituted benzimidazole and compound of isobioquin group and preparation method thereof Download PDFInfo
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- CN110078737A CN110078737A CN201910507221.0A CN201910507221A CN110078737A CN 110078737 A CN110078737 A CN 110078737A CN 201910507221 A CN201910507221 A CN 201910507221A CN 110078737 A CN110078737 A CN 110078737A
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses a kind of perfluoroalkyl substituted benzimidazole and compound of isobioquin group and preparation method thereof.The present invention is using N- methylacryloyl -2-Phenylbenzimidazole class compound and perfluoroalkyl iodide as raw material, synthesizing perfluoroalkyl substituted benzimidazole and compound of isobioquin group under the action of TMEDA (tetraethyl diamines).This method have the advantages that raw material is cheap and easy to get, reaction condition is mild, it is easy to operate, be easy to amplify, have industrialized production and application prospect.The analog derivative has potential application in research fields such as medicine/organic syntheses, and the present invention provides new method for the synthesis of benzimidazole and compound of isobioquin group.
Description
Technical field
The present invention relates to the field of chemical synthesis, and in particular to a kind of perfluoroalkyl substituted benzimidazole and isobioquin group
Close the preparation method of object.
Background technique
Benzimidazole and compound of isobioquin group are a kind of important skeletons, in biochemistry, pharmaceutical chemistry and material
Chemistry etc. has diversified application.Such as it has been applied to anti-inflammatory agent, antidiabetic even antineoplastic etc..Due to
Its structural consequences, researcher are to prepare benzimidazole and compound of isobioquin group has made a large amount of effort.Such as I
By decarboxylation coupling reaction realize such compound synthesis (Chem. Commun.,2019, 55(19), 2861-
2864.).But the method use the oxidants of silver and equivalent.
Meanwhile it being fluorinated functional group and being increasingly being applied to drug, agrochemical industry and materials science field.By fluorine
Change moieties to be introduced into bioactive molecule to its physical chemistry and biological property with profound influence, leads to the parent of enhancing
Lipid, bioavilability and metabolic stability.A kind of effective and convenient photocatalysis is disclosed without metal without photosensitive in we
The free radical cyclization of agent, perfluoroalkyl substituted benzimidazole and compound of isobioquin group are by being simply functionalized N- methyl
It is prepared by the one pot reaction of acryloyl group -2-Phenylbenzimidazole and the perfluoroalkyl iodide being easy to get under mild reaction conditions.This is
Realization for the first time prepares perfluoroalkyl substituted benzimidazole and compound of isobioquin group.
Summary of the invention
The invention proposes the preparation method of a kind of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, the conjunctions
Mild at method reaction condition, handy and safe, raw material is cheap and easy to get, is a kind of environmental-friendly green synthesis method.
It realizes the technical scheme is that a kind of benzimidazole and compound of isobioquin group, structural formula are as follows:
,
Wherein, R1For methyl, methoxyl group, ethyl, chlorine, bromine, trifluoromethyl etc.；RfFor C4F9、C5F11,C10F21。
The preparation method of the perfluoroalkyl substituted benzimidazole and compound of isobioquin group, steps are as follows: will be fragrant
Base benzimidazoles compound and perfluoroalkyl iodide are dissolved in acetonitrile solvent, and TMEDA (tetraethyl diamines) illumination is then added
Under reacted, after reaction, decompression boils off solvent, obtains perfluoroalkyl substituted benzimidazole and isoquinoline through column chromatography for separation
Quinoline ketone compounds.
The structural formula of the N- methylacryloyl -2-Phenylbenzimidazole is as follows:
,
Wherein R1For methyl, methoxyl group, ethyl, chlorine, trifluoromethyl etc..
The preparation method of the perfluoroalkyl substituted benzimidazole and compound of isobioquin group, steps are as follows: by N-
Methylacryloyl -2-Phenylbenzimidazole class compound and perfluoroalkyl iodide are dissolved in acetonitrile solvent, and TMEDA is then added
It is reacted, after reaction, decompression boils off solvent, obtains benzimidazole and compound of isobioquin group through column chromatography for separation.
The structural formula of the perfluoroalkyl substituted benzimidazole and compound of isobioquin group is as follows:
,
Wherein, R1For methyl, methoxyl group, ethyl, chlorine, trifluoromethyl etc..RfFor C4F9、C5F11,C10F21,CF2COOEt etc..
The solvent is acetonitrile；
The aryl benzimidazole, perfluoroalkyl iodide, TMEDA molar ratio be 1:2:2.
The reaction temperature is 35 DEG C, and the reaction time is 12 h.
Reaction light source is 25 W LED light, and reaction carries out under nitrogen protection.
The reaction formula of preparation method of the present invention is as follows:
,
The beneficial effects of the present invention are: the present invention provides a kind of photocatalysis perfluoroalkyl substituted benzimidazole and isobioquin groups
The preparation method of compound, the method mild condition, no metal are easy to operate, regioselectivity is high, yield without photosensitizer
Height is conducive to industrialized production, and the synthesis for benzimidazole and compound of isobioquin group provides new method.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical solution of the present invention is clearly and completely described, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
Those of ordinary skill in the art's every other embodiment obtained under that premise of not paying creative labor, belongs to this hair
The range of bright protection.
Embodiment 1
The preparation method of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, steps are as follows:
N- methylacryloyl -2-Phenylbenzimidazole (0.2 mmol) is added in 25 mL reaction tubes, perfluor butyl iodide
(0.4 mmol), TMEDA (tetraethyl diamines) (0.4 mmol), 2mL acetonitrile, nitrogen protection, the 25 W blue at 35 DEG C
LEDs irradiation is lower to stir 12 h.After reaction, decompression boils off solvent, silica gel column chromatography separation, and the yield for obtaining final product is
76%。
Concrete outcome is as follows:
,
1H NMR (400 MHz, Chloroform-d) δ 8.53 (dd, J = 7.7, 1.5 Hz, 1H), 8.36 (m,
3.1 Hz, 1H), 7.84 (dd, J = 6.4, 2.6 Hz, 1H), 7.65 – 7.40 (m, 5H), 3.66 – 3.46
(m, 1H), 2.91 (m, 1H), 1.79 (s, 3H). 13C NMR (101 MHz, Chloroform-d) δ 170.99,
149.26, 144.07, 138.67, 131.54, 131.43, 128.41, 126.52 (d, J = 2.7 Hz),
126.32, 126.14, 125.79, 122.25, 119.96, 115.76, 124.399 – 105.689 (m), 44.93
(d, J = 3.0 Hz), 40.14, 31.63. 19F NMR (376 MHz, Chloroform-d) δ -81.11 (d, J
= 10.4 Hz, 3F), -107.84 (dd, J = 273.8, 14.7 Hz, 1F), -111.43 – -112.67 (m,
1F), -124.70 (s, 2F), -125.53 – -126.19 (m, 4F)。
Embodiment 2
The preparation method of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, steps are as follows:
N- methylacryloyl -2-Phenylbenzimidazole (0.2 mmol) is added in 25 mL reaction tubes, perfluor iodo-pentane
(0.4 mmol), TMEDA (0.4 mmol), 2mL acetonitrile, nitrogen protection stir under 25 W blue led s irradiation at 35 DEG C
12 h.After reaction, decompression boils off solvent, and silica gel column chromatography separation, the yield for obtaining final product is 80%.
The following concrete outcome of concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.54 (d, J = 7.9 Hz, 1H), 8.37 (d, J =
6.6 Hz, 1H), 7.85 (m, 1H), 7.66 – 7.40 (m, 5H), 3.55 (dd, J = 32.9, 15.2 Hz,
1H), 2.91 (m, 1H), 1.78 (s, 1H). 13C NMR (101 MHz, Chloroform-d) δ 170.98,
149.25, 144.09, 138.68, 131.52, 131.44, 128.38, 126.50 (d, J = 2.6 Hz),
126.32, 126.11, 125.77, 122.28, 119.96, 115.75, 121.83 – 104.99 (m), 44.95
(d, J = 3.0 Hz), 40.26 (t, J = 19.6 Hz), 31.58. 19F NMR (376 MHz, Chloroform-d) δ -80.88 (d, J = 10.2 Hz, 3F), -107.69 (m, 1F), -111.94 (m, 1F), -122.57
(m, 2F), -124.03 (t, J = 13.7 Hz, 2F), -125.90 – -126.95 (m, 2F)。
Embodiment 3
The preparation method of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, steps are as follows:
N- methylacryloyl -2-Phenylbenzimidazole (0.2 mmol) is added in 25 mL reaction tubes, perfluor iodo certain herbaceous plants with big flowers alkane
(0.4 mmol), TMEDA (0.4 mmol), 2mL acetonitrile, nitrogen protection stir under 25 W blue led s irradiation at 35 DEG C
12 h.After reaction, decompression boils off solvent, and silica gel column chromatography separation, the yield for obtaining final product is 64%.
Concrete outcome is as follows:
,
1H NMR (400 MHz, Chloroform-d) δ 8.54 (dd, J = 7.8, 1.5 Hz, 1H), 8.37
(dd, J = 6.7, 2.4 Hz, 1H), 7.85 (dd, J = 6.4, 2.3 Hz, 1H), 7.62 – 7.41 (m,
5H), 3.55 (dd, J = 32.9, 15.4 Hz, 1H), 2.91 (m, 1H), 1.78 (s, 3H). 13C NMR
(101 MHz, Chloroform-d) δ 170.98, 149.25, 144.07, 138.68, 131.54 (d, J = 5.9
Hz), 131.43, 128.42 (d, J = 5.8 Hz), 126.50 (d, J = 2.5 Hz), 126.35 (d, J =
5.7 Hz), 126.15 (d, J = 6.0 Hz), 125.81 (d, J = 5.9 Hz), 122.29 (d, J = 5.7
Hz), 119.98 (d, J = 5.7 Hz), 115.78 (d, J = 5.8 Hz), 118.50 – 107.74 (m),
44.95 (d, J = 3.0 Hz), 40.26 (t, J = 19.5 Hz), 31.65. 19F NMR (376 MHz,
Chloroform-d) δ -80.90 (t, J = 10.1 Hz, 3F), -107.67 (m, 1F), -111.89 (m,
1F), -121.59 (s, 2F), -121.95 (d, J = 39.7 Hz, 8F), -122.83 (d, J = 17.3 Hz,
2F), -123.84 (d, J = 17.0 Hz, 2F), -126.22 (d, J = 14.7 Hz, 2F)。
Embodiment 4
The preparation method of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, steps are as follows:
N- methylacryloyl -2- p-methylphenyl benzimidazole (0.2 mmol) is added in 25 mL reaction tubes, perfluor iodo fourth
Alkane (0.4 mmol), TMEDA (0.4 mmol), 2 mL acetonitriles, nitrogen protection are stirred under 25 W blue led s irradiation at 35 DEG C
Mix 12 h.After reaction, decompression boils off solvent, and silica gel column chromatography separation, the yield for obtaining final product is 73%.
Concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.41 (m, 1H), 8.36 (dd, J = 7.0, 2.7 Hz,
1H), 7.86 – 7.78 (m, 1H), 7.43 (m, 2H), 7.37 – 7.30 (m, 1H), 7.27 (d, J = 3.1
Hz, 1H), 3.54 (dd, J = 33.0, 15.5 Hz, 1H), 2.90 (m, 1H), 2.46 (t, J = 2.4 Hz,
3H), 1.77 (t, J = 2.4 Hz, 3H). 13C NMR (101 MHz, Chloroform-d) δ 171.14,
149.52, 144.14, 142.22, 138.72, 131.41, 129.49, 126.89 (d, J = 2.3 Hz),
126.22, 126.00, 125.49, 119.76, 119.60, 115.67, 121.84 – 105.34 (m), 44.87
(d, J = 2.9 Hz), 40.10 (t, J = 19.6 Hz), 31.57, 21.73. 19F NMR (376 MHz,
Chloroform-d) δ -81.27 (t, J = 9.9 Hz, 3F), -108.00 (m. 1F), -112.32 (m, 1F),
-124.83 (d, J = 13.1 Hz, 1F), -125.96 (dd, J = 17.9, 9.4 Hz, 2F), -126.07 (m,
2F)。
Embodiment 5
The preparation method of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, steps are as follows:
N- methylacryloyl -2- p-methoxyphenyl benzimidazole (0.2 mmol) is added in 25 mL reaction tubes, perfluor iodine
For butane (0.4 mmol), TMEDA (0.4 mmol), 2 mL acetonitriles, nitrogen protection, 25 W blue led s irradiate at 35 DEG C
12 h of lower stirring.After reaction, decompression boils off solvent, and silica gel column chromatography separation, the yield for obtaining final product is 72%.
Concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.47 (d, J = 8.8 Hz, 1H), 8.33 (dd, J =
7.5, 1.6 Hz, 1H), 7.84 – 7.74 (m, 1H), 7.42 (m, 2H), 7.08 (dd, J = 8.8, 2.4
Hz, 1H), 6.95 (d, J = 2.2 Hz, 1H), 3.92 (s, 3H), 3.63 – 3.44 (m, 1H), 2.95 –
2.76 (m, 1H), 1.77 (s, 3H). 13C NMR (101 MHz, Chloroform-d) δ 170.95, 162.33,
149.42, 144.22, 140.75, 131.36, 128.29, 126.00, 125.27, 119.55, 115.60,
115.15, 113.93, 112.48 (d, J = 2.7 Hz), 121.51 – 108.41 (m), 55.61, 45.09 (d,J = 3.0 Hz), 40.22 (t, J = 19.8 Hz), 31.81. 19F NMR (376 MHz, Chloroform-d) δ
-81.08 (t, J = 10.4 Hz, 3F), -107.79 (d, J = 274.3 Hz, 1F), -112.15 (d, J =
274.5 Hz, 1F), -124.67 (s, 2F), -125.89 (m, 2F)。
Embodiment 6
The preparation method of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, steps are as follows:
N- methylacryloyl -2- is added in 25 mL reaction tubes to ethylphenyl benzimidazole (0.2 mmol), perfluor iodo
Butane (0.4 mmol), TMEDA (0.4 mmol), 2 mL acetonitriles, nitrogen protection, at 35 DEG C under 25 W blue led s irradiation
Stir 12 h.After reaction, decompression boils off solvent, and silica gel column chromatography separation, the yield for obtaining final product is 72%.
Concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.44 (d, J = 8.1 Hz, 1H), 8.39 – 8.31
(m, 1H), 7.86 – 7.78 (m, 1H), 7.48 – 7.34 (m, 3H), 7.28 (s, 1H), 3.64 – 3.44
(m, 1H), 2.92 (m, 1H), 2.76 (q, J = 7.6 Hz, 2H), 1.77 (s, 3H), 1.29 (t, J =
7.6 Hz, 3H). 13C NMR (101 MHz, Chloroform-d) δ 171.19, 149.52, 148.45, 144.15,
138.74, 131.40, 128.31, 126.38, 126.04, 125.82 (d, J = 2.4 Hz), 125.52,
119.78, 115.69, 121.51 – 108.41 (m), 44.99 (d, J = 3.1 Hz), 40.07 (t, J =
19.6 Hz), 31.74, 29.18, 15.27. 19F NMR (376 MHz, Chloroform-d) δ -81.13 (t, J
= 9.7 Hz, 3F), -107.83 (m,1F), -112.15 (m,1F), -124.77 (q, J = 11.0, 10.1 Hz,
2F), -125.73 – -126.14 (m, 2F)。
Embodiment 7
The preparation method of benzimidazole and compound of isobioquin group, steps are as follows:
N- methylacryloyl -2- rubigan benzimidazole (0.2 mmol) is added in 25 mL reaction tubes, other test sides
With embodiment 1, concrete outcome is as follows for method and condition:
1H NMR (400 MHz, Chloroform-d) δ 8.47 (d, J = 8.5 Hz, 1H), 8.38 – 8.31
(m, 1H), 7.86 – 7.80 (m, 1H), 7.54 – 7.42 (m, 4H), 3.65 – 3.46 (m, 1H), 2.86
(m, 1H), 1.79 (s, 3H). 13C NMR (101 MHz, Chloroform-d) δ 170.26, 148.31,
143.98, 140.30, 137.84, 131.35, 129.08, 127.71, 126.75 (d, J = 2.3 Hz),
126.30, 126.04, 120.91, 120.04, 115.74, 121.79 – 105.66 (m), 44.93 (d, J =
3.0 Hz), 40.22 (t, J = 19.7 Hz), 31.41. 19F NMR (376 MHz, Chloroform-d) δ -
81.19 (d, J = 10.6 Hz, 3F), -107.69 (m,1F), -112.19 (m, 1F), -124.70 (d, J =
11.5 Hz, 2F), -125.99 (m, 2F)。
Embodiment 8
The preparation method of benzimidazole and compound of isobioquin group, steps are as follows:
N- methylacryloyl -2- p-trifluoromethyl phenyl benzimidazole (0.2 mmol) is added in 25 mL reaction tubes, other
With embodiment 1, concrete outcome is as follows for test method and condition:
1H NMR (400 MHz, Chloroform-d) δ 8.67 (d, J = 8.2 Hz, 1H), 8.44 – 8.32
(m, 1H), 7.95 – 7.83 (m, 1H), 7.79 (dd, J = 8.3, 1.6 Hz, 1H), 7.73 (s, 1H),
7.55 – 7.44 (m, 2H), 3.70 – 3.52 (m, 1H), 3.03 – 2.85 (m, 1H), 1.83 (s, 3H).13C NMR (101 MHz, Chloroform-d) δ 170.11, 147.69, 143.96, 139.24, 133.19 (q, J
= 32.9 Hz), 131.40, 127.02, 126.50 (d, J = 4.4 Hz), 125.54, 125.27 (q, J =
3.6 Hz), 124.82, 123.67 (q, J = 3.9 Hz), 122.12, 120.37, 115.86, 121.44 –
109.76 (m), 45.12 (d, J = 3.3 Hz), 40.22 (t, J = 19.8 Hz), 31.41. 19F NMR (376
MHz, Chloroform-d) δ -59.59 – -70.61 (m, 3F), -81.22 (d, J = 10.5 Hz, 3F), -
107.51 (d, J = 274.4 Hz, 1F), -111.93 (d, J = 273.7 Hz, 1F), -124.34 – -
126.62 (m, 4F)。
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (6)
1. a kind of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, it is characterised in that structural formula is as follows:
,
Wherein, R1For methyl, methoxyl group, ethyl, chlorine, bromine, trifluoromethyl etc.；RfFor C4F9、C5F11, C10F21。
2. the preparation method of perfluoroalkyl substituted benzimidazole and compound of isobioquin group, it is characterised in that steps are as follows: will
N- methylacryloyl -2-Phenylbenzimidazole class compound and perfluoroalkyl iodide are dissolved in acetonitrile solvent, are then added
It is reacted under TMEDA (tetraethyl diamines) illumination, after reaction, decompression boils off solvent, obtains perfluor through column chromatography for separation
Alkyl substituted benzene and imidazo compound of isobioquin group.
3. the preparation method of perfluoroalkyl substituted benzimidazole according to claim 2 and compound of isobioquin group,
It is characterized in that the N- methylacryloyl -2-Phenylbenzimidazole class compound structural formula is as follows:
,
Wherein R1For R1For methyl, methoxyl group, ethyl, chlorine, bromine, trifluoromethyl etc..
4. the preparation method of perfluoroalkyl substituted benzimidazole according to claim 2 and compound of isobioquin group,
Be characterized in that: the solvent is acetonitrile.
5. the preparation method of perfluoroalkyl substituted benzimidazole according to claim 2 and compound of isobioquin group,
It is characterized in that: the N- methylacryloyl -2-Phenylbenzimidazole class compound, perfluoroalkyl iodide, TMEDA (tetraethyl two
Amine) molar ratio be 1:2:2.
6. the preparation method of perfluoroalkyl substituted benzimidazole according to claim 2 and compound of isobioquin group,
Be characterized in that: the reaction temperature is 35 DEG C, and the reaction time is 12 h, nitrogen protection, the irradiation of 25 w blue LED lamps.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112851670A (en) * | 2021-01-19 | 2021-05-28 | 深圳大学 | Simple synthesis method of 3-polyfluoroalkyl substituted imidazo [1,2-a ] pyridine |
| CN113373465A (en) * | 2021-05-13 | 2021-09-10 | 北京工业大学 | Method for synthesizing silicon-based substituted benzimidazolo isoquinolinone compounds through photoelectric concerted catalysis |
| CN114105981A (en) * | 2021-12-14 | 2022-03-01 | 怀化学院 | Method for preparing benzimidazole [2,1-a ] isoquinoline-6 (5H) -ketone compound |
| CN116157402A (en) * | 2020-08-06 | 2023-05-23 | 默克专利有限公司 | Material for organic electroluminescent device |
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| KR20150037712A (en) * | 2013-09-30 | 2015-04-08 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
| CN109824666A (en) * | 2019-03-19 | 2019-05-31 | 青岛农业大学 | The synthetic method and products therefrom of isoquinoline compound |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20150037712A (en) * | 2013-09-30 | 2015-04-08 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
| CN109824666A (en) * | 2019-03-19 | 2019-05-31 | 青岛农业大学 | The synthetic method and products therefrom of isoquinoline compound |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116157402A (en) * | 2020-08-06 | 2023-05-23 | 默克专利有限公司 | Material for organic electroluminescent device |
| CN112851670A (en) * | 2021-01-19 | 2021-05-28 | 深圳大学 | Simple synthesis method of 3-polyfluoroalkyl substituted imidazo [1,2-a ] pyridine |
| CN113373465A (en) * | 2021-05-13 | 2021-09-10 | 北京工业大学 | Method for synthesizing silicon-based substituted benzimidazolo isoquinolinone compounds through photoelectric concerted catalysis |
| CN114105981A (en) * | 2021-12-14 | 2022-03-01 | 怀化学院 | Method for preparing benzimidazole [2,1-a ] isoquinoline-6 (5H) -ketone compound |
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Application publication date: 20190802 |