CN105566198B - A kind of 3 dicarbapentaborane substituent indole compounds and preparation method thereof - Google Patents

A kind of 3 dicarbapentaborane substituent indole compounds and preparation method thereof Download PDF

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CN105566198B
CN105566198B CN201610093946.6A CN201610093946A CN105566198B CN 105566198 B CN105566198 B CN 105566198B CN 201610093946 A CN201610093946 A CN 201610093946A CN 105566198 B CN105566198 B CN 105566198B
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dicarbapentaborane
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substituent indole
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CN105566198A (en
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闫建伟
李昆
倪天军
闫福林
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Xinxiang Medical School
Xinxiang Medical University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • 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
    • 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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  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention discloses a kind of 3 dicarbapentaborane substituent indole compounds and preparation method thereof, belong to the synthesis technical field of indole derivatives.Technical scheme main points are：A kind of 3 dicarbapentaborane substituent indole compounds, have following general structure：

Description

A kind of 3 dicarbapentaborane substituent indole compounds and preparation method thereof
Technical field
The invention belongs to the synthesis technical field of indole derivatives, and in particular to a kind of 3 dicarbapentaborane substituent indoles Compound and preparation method thereof.
Background technology
Indoles heterocycle is widely present in bioactive natural product and drug molecular structure, its functionalization be organic compound and One of pharmaceutical chemical priority research areas.The Benzazole compounds of 3 dicarbapentaborane substitutions are a kind of natural productions of important activity Thing and drug molecule, have anti parasitic, antiatherosclerosis, the multiple biological activities such as anticancer, antiviral.Up to now, Its preparation method is mainly reacted by the friedel-craft of indoles and oxalyl chloride, indoles 3 and α-amido ketone, fragrant methyl ketone and α -one aldehyde Oxidative coupling reaction, reaction substrate limited to.β-carbonyl nitrile compounds prepare 3 two carbonyls with indoles by cascade reaction Base substituent indole compound has no report, and such compound is in the fully synthetic and drug molecule various of bioactive natural product Property synthesis in terms of have broad application prospects.
The content of the invention
The technical problem to be solved by the present invention is to provide a kind of 3 dicarbapentaborane substituent indole compounds.
Another technical problem that the present invention solves there is provided a kind of preparation of 3 dicarbapentaborane substituent indole compounds Method, this method are in 4- oxygen -2,2,6,6- tetramethyl piperidine oxygen by substituent indole compound and β-carbonyl nitrile compounds Compound（4-oxo-TEMPO）Under the action of pass through cascade reaction synthesize 3 dicarbapentaborane substituent indole compounds.
The present invention adopts the following technical scheme that to solve above-mentioned technical problem：A kind of 3 dicarbapentaborane substituent indole chemical combination Thing, it is characterised in that there is following general structure：
Wherein R1For alkyl, phenyl, substituted-phenyl, furyl or thienyl；
R2For hydrogen, alkyl or benzyl；
R3For hydrogen, alkyl or phenyl；
R4For hydrogen, alkyl, halogen, hydroxyl or alkoxy.
Further limit, described 3 dicarbapentaborane substituent indole compounds are one of following compounds：
。
The preparation method of 3 dicarbapentaborane substituent indole compounds of the present invention, it is characterised in that concretely comprise the following steps： By substituent indole compound 1, β-carbonyl nitrile compounds 2 and 4- oxo -2,2,6,6- tetramethyl piperidine oxides 4-oxo- 3 dicarbapentaborane substitutions are made by one kettle way multicomponent cascade reaction in acid flux material under the action of copper salt in TEMPO Benzazole compounds 3, the equation of reaction process are：
。
Further limit, the substituent indole compound, β-carbonyl nitrile compounds, 4- oxos -2,2,6,6- tetra- The molar ratio of methyl piperidine oxide and copper salt is 1:1-1.5:2-3:0.05-0.2.
Further limit, the copper salt is CuCl, CuCl2、CuBr、CuBr2Or Cu (OTf)2。
Further limit, the acid flux material is acetic acid, propionic acid or butyric acid.
Further limit, the reaction temperature in reaction process is 25-100 DEG C.
The present invention has synthesized 3 double carbonyls with β-carbonyl nitrile compounds by substituent indole compound by cascade reaction Base Benzazole compounds, are its further derivatization research, synthesize the drug molecule containing indole structure and lay a good foundation.
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 Analyse 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..Shown using the methods of iodine, Ultraluminescence Color.Organic solvent is removed under reduced pressure to carry out in Rotary Evaporators.
Embodiment 1
By 58.5 mg of raw material compound indoles（0.5 mmol）, 109 mg of benzoyl acetonitrile（0.75 mmol）, 4- oxos- 255 mg of 2,2,6,6- tetramethyl piperidine oxides（1.5 mmol）With 5 mg of CuCl（0.05 mmol）3 mL glacial acetic acid are dissolved in, By the open 25 DEG C of reactions 3 of reaction system it is small when, boil off 50 mL of acetic acid, add ethyl acetate to dissolve residue, use saturated sodium bicarbonate Solution washes twice (10 mL × 2), separates organic layer, anhydrous sodium sulfate drying, filtering, revolving removing solvent, pillar layer separation Obtain 108 mg of compound 3-1 sterlings（Yield 87%）.
1H NMR (400 MHz, Acetone-D6) δ 11.38 (s, 1H), 8.41 – 8.34 (m, 1H), 8.13 (d, J = 3.2 Hz, 1H), 8.06 (dt, J = 8.5, 1.5 Hz, 2H), 7.75 – 7.68 (m, 1H), 7.64 – 7.54 (m, 3H), 7.37 – 7.30 (m, 2H)。
Embodiment 2
In addition to replacing benzoyl acetonitrile using 2- chlorobenzoylacetonitriles, in the method identical with prepare compound 3-1 Prepare compound 3-2.
1H NMR (400 MHz, DMSO-D6) δ 12.45 (s, 1H), 8.36 (d, J = 3.2 Hz, 1H), 8.21 – 8.13 (m, 1H), 7.81 (dd, J = 7.6, 1.5 Hz, 1H), 7.67 (td, J = 7.8, 1.6 Hz, 1H), 7.62 – 7.49 (m, 3H), 7.35 – 7.25 (m, 2H)。
Embodiment 3
Except replacing benzoyl acetonitrile using 3- chlorobenzoylacetonitriles, CuBr instead of beyond CuCl, with prepare compound Method prepare compound 3-3 identical 3-1.
1H NMR (400 MHz, DMSO-D6) δ 12.48 (s, 1H), 8.24 (s, 2H), 7.95 (s, 1H), 7.92 (d, J = 7.6 Hz, 1H), 7.82 (d, J = 7.6 Hz, 1H), 7.63 (t, J = 7.8 Hz, 1H), 7.56 (d, J = 4.7 Hz, 1H), 7.37 – 7.27 (m, 2H)。
Embodiment 4
Except replacing benzoyl acetonitrile, CuBr using 4- chlorobenzoylacetonitriles2Beyond CuCl, with prepare compound Method prepare compound 3-4 identical 3-1.
1H NMR (400 MHz, DMSO-D6) δ 12.45 (s, 1H), 8.22 (t, J = 4.9 Hz, 2H), 7.98 (d, J = 8.5 Hz, 2H), 7.67 (d, J = 8.4 Hz, 2H), 7.59 – 7.52 (m, 1H), 7.36 – 7.27 (m, 2H)。
Embodiment 5
Except replacing benzoyl acetonitrile, Cu (OTf) using 4- toluyls acetonitrile2Beyond CuCl, with preparation Method prepare compound 3-5 identical compound 3-1.
1H NMR (400 MHz, DMSO-D6) δ 12.40 (s, 1H), 8.26 – 8.18 (m, 1H), 8.15 (s, 1H), 7.86 (d, J = 8.1 Hz, 2H), 7.59 – 7.51 (m, 1H), 7.40 (d, J = 8.0 Hz, 2H), 7.31 (p, J = 6.5 Hz, 2H), 2.40 (s, 3H)。
Embodiment 6
Except 4- methoxybenzoyl acetonitriles replace benzoyl acetonitrile, propionic acid is replaced beyond acetic acid, with prepare compound Method prepare compound 3-6 identical 3-1.
1H NMR (400 MHz, DMSO-D6) δ 12.36 (s, 1H), 8.25 – 8.16 (m, 1H), 8.12 (s, 1H), 7.97 – 7.88 (m, 2H), 7.59 – 7.50 (m, 1H), 7.30 (dt, J = 6.7, 3.6 Hz, 2H), 7.16 – 7.06 (m, 2H), 3.86 (s, 3H)。
Embodiment 7
Except replacing benzoyl acetonitrile using 4- fluorobenzoyls acetonitrile, butyric acid instead of beyond acetic acid, with prepare compound Method prepare compound 3-7 identical 3-1.
1H NMR (500 MHz, DMSO-D6) δ: 12.44 (s, 1H), 8.24 (s, 1H), 8.20 (d, J = 3.5 Hz, 1H), 8.08-8.05 (m, 2H), 7.58-7.56 (m, 1H), 7.41 (t, J = 9.0 Hz, 2H), 7.34-7.29 (m, 2H)。
Embodiment 8
In addition to replacing benzoyl acetonitrile using 3- Bromophenacyls acetonitrile, in the method identical with prepare compound 3-1 Prepare compound 3-8.
1H NMR (400 MHz, DMSO-D6) δ 12.48 (s, 1H), 8.23 (dd, J = 8.6, 3.7 Hz, 2H), 8.09 (t, J = 1.7 Hz, 1H), 7.96 (dd, J = 7.9, 1.8 Hz, 2H), 7.59 – 7.54 (m, 2H), 7.35 – 7.30 (m, 2H)。
Embodiment 9
In addition to replacing benzoyl acetonitrile using 2- furoyls acetonitrile, in the method identical with prepare compound 3-1 Prepare compound 3-9.
1H NMR (400 MHz, DMSO-D6) δ 12.42 (s, 1H), 8.29 (d, J = 3.2 Hz, 1H), 8.25 – 8.16 (m, 2H), 7.56 (ddd, J = 7.7, 6.1, 3.4 Hz, 2H), 7.36 – 7.25 (m, 2H), 6.81 (dd, J = 3.6, 1.6 Hz, 1H)。
Embodiment 10
In addition to replacing benzoyl acetonitrile using 2- thenoyls acetonitrile, in the method identical with prepare compound 3-1 Prepare compound 3-10.
1H NMR (400 MHz, DMSO-D6) δ 12.44 (s, 1H), 8.33 (s, 1H), 8.23 (dd, J = 10.6, 5.1 Hz, 2H), 7.96 (d, J = 3.3 Hz, 1H), 7.59 – 7.51 (m, 1H), 7.36 – 7.25 (m, 3H)。
Embodiment 11
By raw material 5- methoxy-Indoles（0.5 mmol）, 109 mg of benzoyl acetonitrile（0.75 mmol）, 4- oxo -2,2, 255 mg of 6,6- tetramethyl piperidine oxides（1.5 mmol）And 5 mg of CuCl（0.05 mmol）3 mL glacial acetic acid are dissolved in, will be anti- The system opening of answering be heated to 100 DEG C reaction 2 it is small when, boil off 50 mL of acetic acid, add ethyl acetate dissolve residue, use unsaturated carbonate Hydrogen sodium solution washes twice (10 mL × 2), separates organic layer, anhydrous sodium sulfate drying, filtering, revolving removing solvent, column chromatography Isolated 124 mg of compound 3-11 sterlings（Yield 89%）.
1H NMR (400 MHz, DMSO-D6) δ 12.31 (s, 1H), 8.09 (d, J = 2.6 Hz, 1H), 7.97 (d, J = 7.4 Hz, 2H), 7.78 – 7.70 (m, 2H), 7.60 (t, J = 7.7 Hz, 2H), 7.46 (d, J = 8.8 Hz, 1H), 6.95 (dd, J = 8.8, 2.5 Hz, 1H), 3.83 (s, 3H)。
Embodiment 12
In addition to replacing 5- methoxy-Indoles using 5- methyl indols, with the method system identical with prepare compound 3-11 Standby compound 3-12.
1H NMR (400 MHz, DMSO-D6) δ 12.31 (s, 1H), 8.10 (d, J = 3.3 Hz, 1H), 8.05 (s, 1H), 7.96 (d, J = 7.3 Hz, 2H), 7.74 (t, J = 7.4 Hz, 1H), 7.59 (t, J = 7.7 Hz, 2H), 7.43 (d, J = 8.3 Hz, 1H), 7.14 (d, J = 8.3 Hz, 1H), 2.45 (s, 3H)。
Embodiment 13
In addition to replacing 5- methoxy-Indoles using 5- fluoro indoles, prepared in the method identical with prepare compound 3-11 Compound 3-13.
1H NMR (400 MHz, Acetone-D6) δ 11.46 (s, 1H), 8.20 (s, 1H), 8.07 – 8.01 (m, 3H), 7.75 – 7.70 (m, 1H), 7.65 – 7.56 (m, 3H), 7.14 (td, J = 9.1, 2.6 Hz, 1H)。
Embodiment 14
In addition to replacing 5- methoxy-Indoles using 5- chloro-indoles, prepared in the method identical with prepare compound 3-11 Compound 3-14.
1H NMR (400 MHz, Acetone-D6) δ 11.51 (s, 1H), 8.37 (d, J = 2.0 Hz, 1H), 8.20 (s, 1H), 8.09 – 8.03 (m, 2H), 7.73 (t, J = 7.4 Hz, 1H), 7.65 – 7.57 (m, 3H), 7.34 (dd, J = 8.7, 2.1 Hz, 1H)。
Embodiment 15
In addition to replacing 5- methoxy-Indoles using 5- bromo indoles, prepared in the method identical with prepare compound 3-1 Compound 3-15.
1H NMR (400 MHz, DMSO-D6) δ 12.59 (s, 1H), 8.36 (d, J = 1.6 Hz, 1H), 8.25 (s, 1H), 7.97 (d, J = 7.3 Hz, 2H), 7.75 (t, J = 7.4 Hz, 1H), 7.60 (t, J = 7.7 Hz, 2H), 7.54 (d, J = 8.6 Hz, 1H), 7.46 (dd, J = 8.6, 1.9 Hz, 1H)。
Embodiment 16
In addition to replacing 5- methoxy-Indoles using 5-OHi, with the method system identical with prepare compound 3-1 Standby compound 3-16.
1H NMR (400 MHz, DMSO-D6) δ 12.18 (s, 1H), 9.22 (s, 1H), 8.01 (d, J = 3.3 Hz, 1H), 7.98 – 7.91 (m, 2H), 7.77 – 7.70 (m, 1H), 7.59 (dd, J = 10.7, 4.8 Hz, 3H), 7.34 (d, J = 8.7 Hz, 1H), 6.79 (dd, J = 8.7, 2.4 Hz, 1H)。
Embodiment 17
In addition to replacing 5- methoxy-Indoles using 6- fluoro indoles, prepared in the method identical with prepare compound 3-11 Compound 3-17.
1H NMR (400 MHz, DMSO-D6) δ 12.46 (s, 1H), 8.25 – 8.17 (m, 2H), 7.97 (d, J = 7.5 Hz, 2H), 7.75 (t, J = 7.4 Hz, 1H), 7.60 (t, J = 7.7 Hz, 2H), 7.36 (dd, J = 9.5, 2.1 Hz, 1H), 7.23 – 7.14 (m, 1H)。
Embodiment 18
In addition to replacing 5- methoxy-Indoles using 6- chloro-indoles, prepared in the method identical with prepare compound 3-11 Compound 3-18.
1H NMR (400 MHz, DMSO-D6) δ 12.50 (s, 1H), 8.28 – 8.16 (m, 2H), 7.97 (d, J = 7.4 Hz, 2H), 7.75 (t, J = 7.1 Hz, 1H), 7.65 – 7.55 (m, 3H), 7.34 (d,J = 8.2 Hz, 1H)。
Embodiment 19
In addition to replacing 5- methoxy-Indoles using 6- bromo indoles, prepared in the method identical with prepare compound 3-11 Compound 3-19.
1H NMR (400 MHz, DMSO-D6) δ 12.52 (s, 1H), 8.23 (s, 1H), 8.15 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.5 Hz, 2H), 7.74 (d, J = 7.2 Hz, 2H), 7.60 (t, J = 7.6 Hz, 2H), 7.46 (dd, J = 8.4, 1.2 Hz, 1H)。
Embodiment 20
In addition to replacing 5- methoxy-Indoles using 7- methyl indols, with the method system identical with prepare compound 3-11 Standby compound 3-20.
1H NMR (400 MHz, DMSO-D6) δ 12.47 (s, 1H), 8.17 (d, J = 3.3 Hz, 1H), 8.06 (d, J = 7.8 Hz, 1H), 8.01 – 7.93 (m, 2H), 7.74 (t, J = 7.2 Hz, 1H), 7.60 (t, J = 7.6 Hz, 2H), 7.22 (t, J = 7.5 Hz, 1H), 7.12 (d, J = 7.1 Hz, 1H), 2.53 (s, 3H)。
Embodiment 21
In addition to replacing 5- methoxy-Indoles using 2 methyl indole, with the method system identical with prepare compound 3-11 Standby compound 3-21.
1H NMR (400 MHz, Acetone-D6) δ 11.22 (s, 1H), 8.03 (d, J = 7.4 Hz, 2H), 7.98 (d, J = 7.4 Hz, 1H), 7.72 (d, J = 7.5 Hz, 1H), 7.60 (t, J = 7.7 Hz, 2H), 7.45 (d, J = 7.1 Hz, 1H), 7.22 – 7.15 (m, 2H), 2.58 (s, 3H)。
Embodiment 22
In addition to replacing 5- methoxy-Indoles using 1- methyl indols, with the method system identical with prepare compound 3-11 Standby compound 3-22.
1H NMR (400 MHz, CDCl3) δ 8.58 (d, J = 4.1 Hz, 1H), 8.20 (d, J = 7.4 Hz, 2H), 7.88 (s, 1H), 7.59 (t, J = 7.2 Hz, 2H), 7.48 (s, 3H), 3.90 (s, 3H)。
Embodiment 23
In addition to replacing 5- methoxy-Indoles using 1- benzylindoles, with the method system identical with prepare compound 3-11 Standby compound 3-23.
1H NMR (400 MHz, CDCl3) δ 8.50 (d, J = 7.8 Hz, 1H), 8.14 – 8.06 (m, 2H), 7.91 (s, 1H), 7.63 (t, J = 7.4 Hz, 1H), 7.50 (t, J = 7.7 Hz, 2H), 7.38 (ddd, J = 8.0, 5.8, 2.5 Hz, 1H), 7.35 – 7.28 (m, 5H), 7.19 – 7.11 (m, 2H)。
Embodiment 24
Except replacing 5- methoxy-Indoles using 1- methyl indols, beyond pivaloyl acetonitrile substituted benzene formyl acetonitrile, with Method prepare compound 3-24 identical prepare compound 3-11.
1H NMR (400 MHz, DMSO-D6) δ 8.16 (d, J = 7.2 Hz, 1H), 8.08 (s, 1H), 7.59 (d, J = 8.0 Hz, 1H), 7.38 – 7.28 (m, 2H), 3.89 (s, 3H), 1.27 (s, 9H)。
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 original 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)

  1. A kind of 1. preparation method of 3 dicarbapentaborane substituent indole compounds, it is characterised in that 3 dicarbapentaborane substituted indoles The general structure of class compound is：Specially one of following compounds：
    Specifically synthesis step is：By substituent indole compound 1, β-carbonyl nitrile compounds 2 and 4- oxo -2,2,6,6- tetramethyls Phenylpiperidines oxide 4-oxo-TEMPO is more by one kettle way in 25-100 DEG C in acid flux material under the action of copper salt 3 dicarbapentaborane substituent indole compounds 3 are made in component cascade reaction, and the equation of reaction 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. 2. the preparation method of 3 dicarbapentaborane substituent indole compounds according to claim 1, it is characterised in that：It is described Substituent indole compound, β-carbonyl nitrile compounds, 4- oxo -2,2,6,6- tetramethyl piperidine oxides and copper salt Molar ratio be 1:1-1.5:2-3:0.05-0.2.
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