CN106496091A - 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 PDF

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CN106496091A
CN106496091A CN201610876090.XA CN201610876090A CN106496091A CN 106496091 A CN106496091 A CN 106496091A CN 201610876090 A CN201610876090 A CN 201610876090A CN 106496091 A CN106496091 A CN 106496091A
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dicarbapentaborane
substituted azole
azole class
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substituted
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CN106496091B (en
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闫建伟
李昆
倪天军
闫福林
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Xinxiang Medical University
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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
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

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, with following general structure：.The invention also discloses the preparation method of 2 dicarbapentaborane substituted azole class compounds.The present invention realizes the double carbonylation of pyrroles 2 by a step cascade reaction, has synthesized a series of multiple functionalized 2 dicarbapentaborane substituted azole class compounds, is its further derivatization research, synthesizes the drug molecule containing pyrrole structure and lay a good foundation.

Description

A kind of 2 dicarbapentaborane substituted azole class compounds and preparation method thereof
Technical field
The invention belongs to the synthesis technical field of azole derivatives, and in particular to a kind of 2 dicarbapentaborane substituted azole classes Compound and preparation method thereof.
Background technology
Pyrrole heterocyclic is widely present in bioactive natural product and drug molecular structure, with blood fat reducing, antibacterial, antitumor With multiple biological activities such as antiviral.Wherein, the azoles of 2 dicarbapentaborane replacements are important active organic points of a class Son, up to now, its preparation method is mainly obtained by the odor type compound oxidation of resting in peace containing Friedel-Crafts reaction and pyrroles, is reacted Substrate is limited to.β-carbonyl nitrile compounds prepare the pyroles chemical combination that 2 dicarbapentaborane replace with pyrroles by cascade reaction Thing has no report, and such compound has broad application prospects in terms of the multiformity synthesis of drug molecule.
Content of the invention
Present invention solves the technical problem that there is provided a kind of 2 dicarbapentaborane substituted azole class compounds and its preparation side Method, the method are that 2,6,6- tetramethyl piperidines are aoxidized in 4- oxygen -2 by substituent indole compound with β-carbonyl nitrile compounds Thing（4-oxo-TEMPO）In the presence of by cascade reaction synthesize 2 dicarbapentaborane substituted azole class compounds.
The present invention is adopted the following technical scheme that for solving above-mentioned technical problem：A kind of 2 dicarbapentaborane substituted azole class chemical combination Thing, it is characterised in that with following general structure：
Wherein R1For hydrogen, alkyl or benzyl, R2For phenyl, substituted-phenyl, furyl or thienyl, taking on substituted-phenyl phenyl ring Dai Jiwei fluorine, chlorine, bromine, methyl or methoxy.
Further preferably, 2 described 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）In the presence of copper salt, 2 dicarbapentaborane are obtained by one kettle way multicomponent cascade reaction in acid flux material and are taken For azoles 3, the reaction equation of preparation process is：
.
Further preferably, described substituted azole class compound, β-carbonyl nitrile compounds, 4- oxygen -2,2,6,6- tetramethyls The mol ratio of phenylpiperidines oxide and copper salt is 1:1-1.5:2-3:0.05-0.2.
Further preferably, described copper salt is CuCl, CuCl2、CuBr、CuBr2Or Cu (OTf)2.
Further preferably, described acid flux material is acetic acid, propanoic acid or butanoic acid.
Further preferably, the reaction temperature in course of reaction is 25-120 DEG C.
The present invention has synthesized 2 two carbonyls by substituted azole class compound and β-carbonyl nitrile compounds 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
By the following examples the above of the present invention is described in further details, but this should not be interpreted as this The scope for inventing above-mentioned theme is only limitted to below example, and all technology that is realized based on the above of the present invention belong to this Bright scope.
Analytical tool and reagent：Proton nmr spectra is recorded with 400 type nuclear magnetic resonance analyser of Bruker ASCEND, chemical potential The unit for moving d is ppm.All reaction dissolvents conventionally carry out purification.Column chromatography silica gel（200-300 mesh）For green grass or young crops Island marine chemical industry subsidiary factory produces.Thin layer chromatography, using the efficient plates of GF254, is Yantai chemical institute production.Preparative thin layer Analysis plate is prepared by oneself, and fixing phase adopts GF254（HG/T2354-92）Silica gel and sodium carboxymethyl cellulose（800-1200）System Standby, respectively Qingdao Marine Chemical Co., Ltd. and Chinese Medicine（Group）Solution on Chemical Reagents in Shanghai company produces.All solvents are equal For analytical reagent, agents useful for same is purchased from Chemical Reagent Co., Ltd., Sinopharm Group.Aobvious using methods such as iodine, Ultraluminescences Color.Removing organic solvent under reduced pressure is carried out in Rotary Evaporators.
Embodiment 1
3-1
By 35 μ L of starting compound pyrroles（0.5mmol）, benzoyl acetonitrile 109mg（0.75mmol）, 4- oxos -2,2,6,6- four Methyl piperidine oxide 255mg（1.5 mmol）And CuCl 5mg（0.05mmol）3mL glacial acetic acid is dissolved in, reaction system is open React 5 hours in 80 DEG C, boil off acetic acid 50mL, plus ethyl acetate dissolving residue, washed twice with saturated sodium bicarbonate solution （10mL×2）, organic layer is separated, anhydrous sodium sulfate drying is filtered, and revolving removes solvent, and pillar layer separation obtains compound 3-1 Sterling 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 replacing benzoyl acetonitrile using 4- chlorobenzoylacetonitriles, to prepare with prepare compound 3-1 identical method 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
Except using 4- toluyls acetonitrile replace benzoyl acetonitrile in addition to, with prepare compound 3-1 identical method system Standby 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
Except using 4- methoxybenzoyl acetonitriles replace benzoyl acetonitrile in addition to, with prepare compound 3-1 identical 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
Except using 4- Fluorobenzoyls acetonitrile replace benzoyl acetonitrile in addition to, with prepare compound 3-1 identical method system Standby 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 replacing benzoyl acetonitrile using thiophene -2- formyls acetonitrile, to prepare with prepare compound 3-1 identical method 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 replacing benzoyl acetonitrile using furan -2- formyls acetonitrile, to prepare with prepare compound 3-1 identical method 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
Except using 2- chlorobenzoyls acetonitrile replace benzoyl acetonitrile in addition to, with prepare compound 3-1 identical method system Standby 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
Except using 3- chlorobenzoyls acetonitrile replace benzoyl acetonitrile in addition to, with prepare compound 3-1 identical method system Standby 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
Except using 3- bromobenzoyls acetonitrile replace benzoyl acetonitrile in addition to, with prepare compound 3-1 identical method system Standby 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
Except using 3- methoxybenzoyl acetonitriles replace benzoyl acetonitrile in addition to, with prepare compound 3-1 identical 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
Except using 2- methoxybenzoyl acetonitriles replace benzoyl acetonitrile in addition to, with prepare compound 3-1 identical 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
Except using N- methylpyrroles replace pyrroles in addition to, with prepare compound 3-1 identical method prepare compound 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
Except using N- N-ethyl pyrrole N -s replace pyrroles in addition to, with prepare compound 3-1 identical method prepare compound 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
Except using N- benzyl-pyrroles replace pyrroles in addition to, with prepare compound 3-1 identical method prepare compound 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).
Ultimate principle, principal character and the advantage of the present invention is embodiment above describes, the technical staff of the industry should Understand, the present invention is not restricted to the described embodiments, the original that the present invention is simply described described in above-described embodiment and description Reason, under the scope without departing from the principle of the invention, the present invention also has various changes and modifications, and these changes and improvements each fall within In the scope of protection of the invention.

Claims (7)

1. a kind of 2 dicarbapentaborane substituted azole class compounds, it is characterised in that with following general structure：
Wherein R1For hydrogen, alkyl or benzyl, R2For phenyl, substituted-phenyl, furyl or thienyl, taking on substituted-phenyl phenyl ring Dai Jiwei fluorine, chlorine, bromine, methyl or methoxy.
2. 2 dicarbapentaborane substituted azole class compound according to claim 1, it is characterised in that 2 described dicarbapentaborane Substituted azole class compound is one of following compounds：
.
3. the preparation method of 2 dicarbapentaborane substituted azole class compounds described in a kind of claim 1, it is characterised in that concrete walk Suddenly it is：By substituted azole class compound 1, β-carbonyl nitrile compounds 2 and 4- oxo -2,2,6,6- tetramethyl piperidine oxides 4- Oxo-TEMPO is obtained 2 dicarbapentaborane by one kettle way multicomponent cascade reaction in the presence of copper salt in acid flux material Substituted azole class compound 3, the reaction equation of preparation process is：
.
4. the preparation method of 2 dicarbapentaborane substituted azole class compound according to claim 3, it is characterised in that：Described Substituted azole class compound, β-carbonyl nitrile compounds, 4- oxygen -2,2,6,6- tetramethyl piperidine oxides and copper salt Mol ratio is 1:1-1.5:2-3:0.05-0.2.
5. the preparation method of 2 dicarbapentaborane substituted azole class compound according to claim 3, it is characterised in that：Described Copper salt be CuCl, CuCl2、CuBr、CuBr2Or Cu (OTf)2.
6. the preparation method of 2 dicarbapentaborane substituted azole class compound according to claim 3, it is characterised in that：Described Acid flux material be acetic acid, propanoic acid or butanoic acid.
7. the preparation method of 2 dicarbapentaborane substituted azole class compound according to claim 3, it is characterised in that：Reaction During reaction temperature be 25-120 DEG C.
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