CN106496091B - A kind of 2 dicarbapentaborane substituted azole class compounds and preparation method thereof - Google Patents
A kind of 2 dicarbapentaborane substituted azole class compounds and preparation method thereof Download PDFInfo
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- CN106496091B CN106496091B CN201610876090.XA CN201610876090A CN106496091B CN 106496091 B CN106496091 B CN 106496091B CN 201610876090 A CN201610876090 A CN 201610876090A CN 106496091 B CN106496091 B CN 106496091B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Abstract
The invention discloses a kind of 2 dicarbapentaborane substituted azole class compounds and preparation method thereof, belong to the synthesis technical field of azole derivatives.Technical scheme main points are：A kind of 2 dicarbapentaborane substituted azole class compounds, have following general structure：
Description
Technical field
The invention belongs to the synthesis technical fields of azole derivatives, and in particular to a kind of 2 dicarbapentaborane substituted azole classes
Close object and preparation method thereof.
Background technology
Pyrrole heterocyclic is widely present in bioactive natural product and drug molecular structure, has reducing blood lipid, antibacterial, antitumor
With the multiple biological activities such as antiviral.Wherein, the azoles of 2 dicarbapentaborane substitutions are a kind of organic point important of activity
Son, up to now, its preparation method are mainly obtained by the odor type compound oxidation of resting in peace containing Friedel-Crafts reaction and pyrroles, reaction
Substrate is limited to.β-carbonyl nitrile compounds prepare the pyroles chemical combination of 2 dicarbapentaborane substitutions with pyrroles by cascade reaction
Object has not been reported, and such compound has broad application prospects in terms of the diversity synthesis of drug molecule.
The content of the invention
The technical problem to be solved by the present invention is to provide a kind of 2 dicarbapentaborane substituted azole class compounds and its preparation sides
Method, this method are in 4- oxygen -2,2, the oxidation of 6,6- tetramethyl piperidines by substituent indole compound and β-carbonyl nitrile compounds
Object（4-oxo-TEMPO）Under the action of pass through cascade reaction synthesize 2 dicarbapentaborane substituted azole class compounds.
The present invention adopts the following technical scheme that solve above-mentioned technical problem：A kind of 2 dicarbapentaborane substituted azole class chemical combination
Object, it is characterised in that there is following general structure：
Wherein R1For hydrogen, alkyl or benzyl, R2For phenyl, substituted-phenyl, furyl or thienyl, on substituted-phenyl phenyl ring
Substituent group for fluorine, chlorine, bromine, methyl or methoxy.
Further preferably, 2 dicarbapentaborane substituted azole class compounds are one of following compounds：
。
The preparation method of 2 dicarbapentaborane substituted azole class compound of the present invention, it is characterised in that concretely comprise the following steps：
By substituted azole class compound 1, β-carbonyl nitrile compounds 2 and 4- oxo -2,2,6,6- tetramethyl piperidine oxides（4-oxo-
TEMPO）Under the action of copper salt, in acid flux material 2 dicarbapentaborane are made by one kettle way multicomponent cascade reaction takes
For azoles 3, the reaction equation of preparation process is：
。
Further preferably, the substituted azole class compound, β-carbonyl nitrile compounds, 4- oxygen -2,2,6,6- tetramethyls
The molar ratio of phenylpiperidines oxide and copper salt is 1:1-1.5:2-3:0.05-0.2.
Further preferably, the copper salt is CuCl, CuCl2、CuBr、CuBr2Or Cu (OTf)2。
Further preferably, the acid flux material is acetic acid, propionic acid or butyric acid.
Further preferably, the reaction temperature in reaction process is 25-120 DEG C.
The present invention has synthesized 2 two carbonyls with β-carbonyl nitrile compounds by substituted azole class compound by cascade reaction
Base substituted azole class compound is its further derivatization research, synthesizes the drug molecule containing pyrrole structure and lay a good foundation.
Specific embodiment
The above of the present invention is described in further details by the following examples, but this should not be interpreted as to this
The scope for inventing above-mentioned theme is only limitted to following embodiment, and all technologies realized based on the above of the present invention belong to this hair
Bright scope.
Analytical instrument and reagent：Nuclear magnetic resonance spectroscopy is recorded with 400 type Nuclear Magnetic Resonance of Bruker ASCEND, chemical potential
The unit for moving d is ppm.All reaction dissolvents are conventionally purified.Column chromatography silica gel（200-300 mesh）For green grass or young crops
Island marine chemical industry subsidiary factory produces.Thin-layer chromatography uses the efficient plates of GF254, is produced for Yantai chemical institute.Preparative thin layer
It analyses plate to be prepared by oneself, stationary phase uses GF254（HG/T2354-92）Silica gel and sodium carboxymethylcellulose（800-1200）System
It is standby, it is respectively Qingdao Marine Chemical Co., Ltd. and Chinese Medicine（Group）Solution on Chemical Reagents in Shanghai company produces.All solvents are equal
For analytical reagents, agents useful for same is purchased from Sinopharm Chemical Reagent Co., Ltd..It is shown using the methods of iodine, Ultraluminescence
Color.Organic solvent is removed under reduced pressure to carry out in Rotary Evaporators.
Embodiment 1
3-1
By 35 μ L of raw material compound pyrroles（0.5mmol）, benzoyl acetonitrile 109mg（0.75mmol）, 4- oxo -2,2,6,
6- tetramethyl piperidine oxides 255mg（1.5 mmol）And CuCl 5mg（0.05mmol）3mL glacial acetic acid is dissolved in, by reaction system
Be open to 80 DEG C reaction 5 it is small when, boil off acetic acid 50mL, add ethyl acetate dissolve residue, washed with saturated sodium bicarbonate solution
Twice（10mL×2）, organic layer, anhydrous sodium sulfate drying are separated, filtering rotates and removes solvent, and pillar layer separation obtains chemical combination
Object 3-1 sterlings 88mg（Yield 93%）.
1H NMR (400 MHz, DMSO-D6) δ 12.51 (brs, 1H), 7.92 (d, J = 7.1 Hz, 2H),
7.76 (t, J = 7.4 Hz, 1H), 7.61 (t, J = 7.7 Hz, 2H), 7.43-7.38 (m, 1H), 6.91-
6.80 (m, 1H), 6.33-6.29 (m, 1H)。
Embodiment 2
3-2
In addition to 4- chlorobenzoylacetonitriles is used to replace benzoyl acetonitrile, in the method identical with prepare compound 3-1
Prepare compound 3-2.
1H NMR (400 MHz, CDCl3) δ 9.99 (brs, 1H), 8.03 (d, J = 8.6 Hz, 2H),
7.50 (d, J = 8.6 Hz, 2H), 7.28-7.24 (m, 1H), 7.13-7.02 (m, 1H), 6.42-6.36 (m,
1H)。
Embodiment 3
3-3
In addition to 4- toluyls acetonitrile is used to replace benzoyl acetonitrile, with the side identical with prepare compound 3-1
Method prepare compound 3-3.
1H NMR (400 MHz, CDCl3) δ 9.88 (brs, 1H), 7.94 (d, J = 8.2 Hz, 2H),
7.30 (d, J = 8.1 Hz, 2H), 7.23-7.19 (m, 1H), 7.05-6.96 (m, 1H), 6.38-6.32 (m,
1H), 2.43 (s, 3H)。
Embodiment 4
3-4
In addition to 4- methoxybenzoyl acetonitriles is used to replace benzoyl acetonitrile, with identical with prepare compound 3-1
Method prepare compound 3-4.
1H NMR (400 MHz, CDCl3) δ 9.71 (brs, 1H), 8.04 (d, J = 8.8 Hz, 2H),
7.23-7.17 (s, 1H), 7.07-7.01 (m, 1H), 6.98 (t, J = 8.9 Hz, 2H), 6.37 (dd, J =
3.7, 2.3 Hz, 1H), 3.90 (s, 3H)。
Embodiment 5
3-5
In addition to 4- Fluorobenzoyls acetonitrile is used to replace benzoyl acetonitrile, with the side identical with prepare compound 3-1
Method prepare compound 3-5.
1H NMR (400 MHz, CDCl3) δ 10.32 (brs, 1H), 8.11 (dd, J = 8.7, 5.4 Hz,
2H), 7.25-7.22 (m, 1H), 7.18 (t, J = 8.6 Hz, 2H), 7.09-7.02 (m, 1H), 6.38
(dd, J = 3.6, 2.3 Hz, 1H)。
Embodiment 6
3-6
In addition to thiophene -2- formyls acetonitrile is used to replace benzoyl acetonitrile, in the method identical with prepare compound 3-1
Prepare compound 3-6.
1H NMR (400 MHz, CDCl3) δ 10.09 (brs, 1H), 8.09 (s, 1H), 7.82 (dd, J =
4.9, 1.0 Hz, 1H), 7.35-7.28 (m, 1H), 7.25-7.21 (m, 1H), 7.19 (dd, J = 4.9,
3.9 Hz, 1H), 6.41-6.35 (m, 1H)。
Embodiment 7
3-7
In addition to furans -2- formyls acetonitrile is used to replace benzoyl acetonitrile, in the method identical with prepare compound 3-1
Prepare compound 3-7.
1H NMR (400 MHz, CDCl3) δ 10.32 (brs, 1H), 7.85-7.77 (m, 1H), 7.76-
7.58 (m, 1H), 7.38 (d, J = 3.4 Hz, 1H), 7.29 (d, J = 3.2 Hz, 1H), 6.68 (d, J
= 2.5 Hz, 1H), 6.45 (d, J = 2.9 Hz, 1H).
Embodiment 8
3-8
In addition to 2- chlorobenzoyls acetonitrile is used to replace benzoyl acetonitrile, with the side identical with prepare compound 3-1
Method prepare compound 3-8.
1H NMR (400 MHz, CDCl3) δ 9.96 (brs, 1H), 7.76 (dd, J = 7.6, 1.6 Hz,
1H), 7.50 (ddd, J = 8.1, 7.3, 1.7 Hz, 1H), 7.47-7.37 (m, 2H), 7.23-7.15 (m,
2H), 6.44-6.36 (m, 1H)。
Embodiment 9
3-9
In addition to 3- chlorobenzoyls acetonitrile is used to replace benzoyl acetonitrile, with the side identical with prepare compound 3-1
Method prepare compound 3-9.
1H NMR (400 MHz, CDCl3) δ 10.15 (brs, 1H), 8.07 (t, J = 1.8 Hz, 1H),
8.02-7.92 (m, 1H), 7.63 (ddd, J = 8.0, 2.1, 1.0 Hz, 1H), 7.47 (t, J = 7.9 Hz,
1H), 7.31-7.25 (m, 1H), 7.13-7.04 (m, 1H), 6.42 – 6.38 (m, 1H); 13C NMR (101
MHz, CDCl3) δ 191.2, 135.2, 134.9, 134.6, 130.3, 130.1, 129.1, 128.5, 122.4,
112.6。
Embodiment 10
3-10
In addition to 3- bromobenzoyls acetonitrile is used to replace benzoyl acetonitrile, with the side identical with prepare compound 3-1
Method prepare compound 3-10.
1H NMR (400 MHz, CDCl3) δ 10.06 (brs, 1H), 8.20 (t, J = 1.7 Hz, 1H),
7.99 (d, J = 7.8 Hz, 1H), 7.77 (ddd, J = 8.0, 1.9, 1.0 Hz, 1H), 7.39 (t, J =
7.9 Hz, 1H), 7.29-7.23 (m, 1H), 7.09-7.02 (m, 1H), 6.42-6.35 (m, 1H)。
Embodiment 11
3-11
In addition to 3- methoxybenzoyl acetonitriles is used to replace benzoyl acetonitrile, with identical with prepare compound 3-1
Method prepare compound 3-11.
1H NMR (400 MHz, CDCl3) δ 10.02 (brs, 1H), 7.64 – 7.53 (m, 2H), 7.40
(t, J = 7.9 Hz, 1H), 7.27-7.15 (m, 2H), 7.03 (d, J = 2.7 Hz, 1H), 6.36 (d, J
= 2.1 Hz, 1H), 3.87 (s, 3H)。
Embodiment 12
3-12
In addition to 2- methoxybenzoyl acetonitriles is used to replace benzoyl acetonitrile, with identical with prepare compound 3-1
Method prepare compound 3-12.
1H NMR (400 MHz, CDCl3) δ 10.07 (br s, 1H), 7.91 (dd, J = 7.7, 1.7 Hz,
1H), 7.62-7.51 (m, 1H), 7.18-7.03 (m, 1H), 7.13-7.06 (m, 1H), 6.95 (d, J =
8.4 Hz, 1H), 6.90 (d, J = 3.5 Hz, 1H), 6.35 – 6.29 (m, 1H), 3.65 (s, 3H)。
Embodiment 13
3-13
In addition to N- methylpyrroles is used to replace pyrroles, with the method prepare compound identical with prepare compound 3-1
3-13。
1H NMR (400 MHz, CDCl3) δ 8.04-7.94 (m, 2H), 7.61 (t, J = 7.4 Hz, 1H),
7.48 (t, J = 7.7 Hz, 2H), 6.99 (s, 1H), 6.86 (dd, J = 4.2, 1.5 Hz, 1H), 6.17
(dd, J = 4.2, 2.4 Hz, 1H), 4.08 (s, 3H)。
Embodiment 14
3-14
In addition to N- N-ethyl pyrrole Ns is used to replace pyrroles, with the method prepare compound identical with prepare compound 3-1
3-14。
1H NMR (400 MHz, CDCl3) δ 7.99 (d, J = 7.5 Hz, 2H), 7.61 (t, J = 7.4
Hz, 1H), 7.48 (t, J = 7.7 Hz, 2H), 7.09-7.06 (m, 1H), 6.87 (d, J = 3.8 Hz,
1H), 6.18 (dd, J = 3.9, 2.5 Hz, 1H), 4.48 (q, J = 7.1 Hz, 2H), 1.48 (t, J =
7.2 Hz, 3H)。
Embodiment 15
3-15
In addition to N- benzyl-pyrroles is used to replace pyrroles, with the method prepare compound identical with prepare compound 3-1
3-15。
1H NMR (400 MHz, CDCl3) δ 7.82-7.77 (m, 2H), 7.61-7.54 (m, 1H), 7.41
(t, J = 7.8 Hz, 2H), 7.38-7.28 (m, 3H), 7.22-7.16 (m, 2H), 7.14-7.10 (m, 1H),
6.96 (dd, J = 4.2, 1.6 Hz, 1H), 6.25 (dd, J = 4.2, 2.5 Hz, 1H), 5.69 (s, 2H)。
Basic principle, main features and advantages embodiment above describes the present invention, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe the originals of the present invention
Reason, under the scope for not departing from the principle of the invention, various changes and modifications of the present invention are possible, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (2)
- A kind of 1. preparation method of 2 dicarbapentaborane substituted azole class compound, it is characterised in that 2 dicarbapentaborane substituted azoles Class compound has following general structure：, it is specially one of following compounds：It concretely comprises the following steps：By substituted azole class compound 1, β-carbonyl nitrile compounds 2 and 4- oxo -2,2,6,6- tetramethyl piperazines Pyridine oxide 4-oxo-TEMPO passes through one kettle way multicomponent in acid flux material under the action of copper salt in 25-120 DEG C 2 dicarbapentaborane substituted azole class compounds 3 are made in cascade reaction, and the reaction equation of preparation process is：The copper salt is CuCl, CuCl2、CuBr、CuBr2Or Cu (OTf)2, the acid flux material is acetic acid, propionic acid or fourth Acid.
- 2. the preparation method of 2 dicarbapentaborane substituted azole class compound according to claim 1, it is characterised in that：It is described Substituted azole class compound, β-carbonyl nitrile compounds, 4- oxygen -2,2,6,6- tetramethyl piperidine oxides and copper salt Molar ratio is 1:1-1.5:2-3:0.05-0.2.
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