CN107739342A - A kind of method of the diarylamino benzimidazolone derivatives of one-step synthesis 5 - Google Patents
A kind of method of the diarylamino benzimidazolone derivatives of one-step synthesis 5 Download PDFInfo
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- CN107739342A CN107739342A CN201711225340.4A CN201711225340A CN107739342A CN 107739342 A CN107739342 A CN 107739342A CN 201711225340 A CN201711225340 A CN 201711225340A CN 107739342 A CN107739342 A CN 107739342A
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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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
Abstract
The invention belongs to technical field of organic synthesis, discloses a kind of method of the diarylamino benzimidazolone derivatives of one-step synthesis 5.In the reactor, add compound 1, compound 2, metallic catalyst, part, oxidant and solvent, 1~24h of stirring reaction at 25~130 DEG C, reaction is cooled to room temperature after terminating, vacuum rotary steam removes solvent and can obtain crude product, and crude by column chromatography purifies to obtain the 5 diarylamino benzimidazolone derivatives；Described compound 1 refers to the compound with formula (1) structure；Described compound 2 refers to the secondary amine or tertiary amine with formula (2) structure, or its corresponding acid salt.The method of the present invention has synthesis step simple, safe operation, advantages of nontoxic raw materials and cheap and easy to get, synthetic method to the advantages of functional group compatibility is good, Atom economy is high.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of one-step synthesis 5- diarylamino benzimidazolones spread out
The method of biology.
Background technology
Benzimidazolone is the derivative of benzimidazole C-2 positions oxidation, is mainly used in dye industry.In recent years, it is related
Research finds that a series of benzimidazole ketone compounds also show extensive Medical bioactive, as antibacterial, it is antiviral, disappear
Inflammation, anti-hypertension, desinsection and (J.B.Wright, Chem.Rev., the 1951,48,397-541 such as antitumor；A.M.Monforte,
A.Rao,P.Logoteta,S.Ferro,L.D.Luca,M.L.Barreca,N.Iraci,G.Maga,E.D.Clercq,
C.Pannecouque,A.Chimirri,Bioorgan Med Chem.,2008,16,7429-7435.)。
The method that tradition prepares benzimidazolone is former for starting by o-dichlorohenzene, o-phenylenediamine or ortho-nitraniline etc.
Material synthesis obtains.(1) using o-dichlorohenzene as raw material：Under the catalysis of copper powder or stannous chloride, o-dichlorohenzene, ammoniacal liquor and carbonic acid
Sodium (or sodium acid carbonate, urea, ethylene carbonate) reaction under conditions of 210-215 DEG C, 6.2-7.8MPa prepares benzimidazole
Ketone.The advantage of this synthetic method is that raw material is easy to get and cheap, but needs to carry out under high temperature, condition of high voltage, pair is set
It is standby to require higher.(2) using o-phenylenediamine as raw material：The carbonylation agent such as o-phenylenediamine and urea, phosgene, carbon monoxide is contracted
Close synthesizing benzimidazole ketone.This method is low for equipment requirements, easy to operate, is adapted to industrialized production.But due to phosgene, one
The raw materials such as carbonoxide are toxic gases, unfriendly to environment, and technical requirements are higher, are restricted in actual applications.(3) with
Ortho-nitraniline is raw material：Main research ortho-nitraniline is from reducing carbonyl reagent carbon monoxide under different catalyst system and catalyzings
Reaction.Although these traditional synthetic methods have raw material to be easy to get and cheap advantage, but need in high temperature, high pressure
Under the conditions of carry out, it is higher to equipment requirement, while also have that product quality is high, a large amount of waste water are produced in production process, be useless
The obvious deficiencies such as slag, environmental pollution be serious.(the synthesis of the big .5- aminobenzimidazoles ketone of Shao Guang and benzimidazoles compound
[D] Dalian University of Technology, 2008).
Wherein, 5-Amino-2-benzimidazolinone is the main intermediate of synthesizing benzimidazole ketone structured pigment, with plastics, oil
The industries such as ink, coating are developed rapidly, and the demand of benzimidazolone is continuously increased both at home and abroad.Therefore, more excellent benzo is studied
Imidazolone synthesis technique is very necessary.(Shen Yongjia benzimidazolone pigments and its application [J] chemical science and technologies market .2001,24
(04):7-11)。
The content of the invention
In place of shortcoming and defect existing for above prior art, it is an object of the invention to provide a kind of one-step synthesis
The method of 5- diarylamino benzimidazolone derivatives.
The object of the invention is achieved through the following technical solutions：
A kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives, comprises the following steps：
In the reactor, compound 1, compound 2, metallic catalyst, part, oxidant and solvent are added, 25~130
1~24h of stirring reaction at DEG C, reaction are cooled to room temperature after terminating, vacuum rotary steam removes solvent and can obtain crude product, crude product
Purify to obtain the 5- diarylaminos benzimidazolone derivatives through column chromatography；
Described compound 1 refers to the compound with formula (1) structure；Described compound 2 refers to formula (2) structure
Secondary amine or tertiary amine, or its corresponding acid salt；
Wherein, R1Represent the methyl of one or more substitutions on aromatic ring, phenyl, methoxyl group, nitro, itrile group, trifluoromethyl,
Ester group, halogenic substituent or hydrogen；R2、R3、R4For alkyl that is identical or differing, substitute alkyl or hydrogen, but R2And R3It is asynchronously
Hydrogen.
Reaction equation involved by above-mentioned synthetic method is shown below：
The preferred schlenk pipes (history Ranque tube) of described reactor.
The mol ratio of the compound 1 and compound 2 is (1~20):1；It is preferred that 2:1.
Described metallic catalyst is copper acetate, copper sulphate, stannous chloride, copper chloride, copper fluoride, copper fluoride, iodate
Mixing more than one or both of cuprous, cuprous bromide, copper bromide, trifluoromethayl sulfonic acid copper.
Described part is containing n-donor ligand, preferably pyridine or pyridine derivate.
Described oxidant is metal oxide, peroxide, have the acid of oxidisability, silver salt and one kind in oxygen or
Two or more mixing, wherein the pressure of oxygen used is 1~30 atmospheric pressure.
Described solvent be acetonitrile, tetrahydrofuran, ethanol, tert-pentyl alcohol, isopropanol, isobutanol, N,N-dimethylformamide,
Mixing more than one or both of dimethyl sulfoxide (DMSO), toluene, paraxylene, first alcohol and water.
Described column chromatography purification eluent used is petroleum ether:Dichloromethane:The volume ratio of ethyl acetate is (0.5
~50):(0~20):1 mixed solvent.
The synthetic method of the present invention has the following advantages that and beneficial effect：
The present invention is using diphenylamine compound and two level or tertiary amine as raw material one-step synthesis 5- diarylamino benzimidazoles
Ketone derivatives, have simple synthesis step, safe operation, advantages of nontoxic raw materials and cheap and easy to get, synthetic method compatible to functional group
Well, the advantages of Atom economy is high.
Brief description of the drawings
Fig. 1 and Fig. 2 is respectively the hydrogen spectrogram and carbon spectrogram of the products therefrom of embodiment 1；
Fig. 3 and Fig. 4 is respectively the hydrogen spectrogram and carbon spectrogram of the products therefrom of embodiment 2；
Fig. 5 and Fig. 6 is respectively the hydrogen spectrogram and carbon spectrogram of the products therefrom of embodiment 3；
Fig. 7 and Fig. 8 is respectively the hydrogen spectrogram and carbon spectrogram of the products therefrom of embodiment 4；
Fig. 9 and Figure 10 is respectively the hydrogen spectrogram and carbon spectrogram of the products therefrom of embodiment 5；
Figure 11 and Figure 12 is respectively the hydrogen spectrogram and carbon spectrogram of the products therefrom of embodiment 6.
Embodiment
With reference to embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are unlimited
In this.
Embodiment 1
0.5 mM of diphenylamines, 0.25 mM of diethylamine, 0.05 mM of copper chloride are added in schlenk pipes,
0.5 mM of pyridine, 1.5 milliliters of isobutanols, at 100 DEG C, O2Under the conditions of (oxygen pressure used is an atmospheric pressure) stirring it is anti-
After answering 12 hours, stop heating and stirring, be cooled to room temperature, vacuum rotary steam removes solvent, then by column chromatographic isolation and purification, obtains
To target product, the volume ratio of column chromatography eluent used is 20:5:1 petroleum ether:Dichloromethane:Ethyl acetate mixing is molten
Agent, yield 78%.
Respectively as depicted in figs. 1 and 2, structural characterization data are as follows for the hydrogen spectrogram and carbon spectrogram of products therefrom：
1H NMR(400MHz,CDCl3) δ 7.58-7.48 (m, 4H), 7.37 (t, J=7.1Hz, 1H), 7.20-7.26 (m,
4H), 7.08 (d, J=7.9Hz, 4H), 6.97 (t, J=7.6Hz, 3H), 6.87 (s, 1H), 6.81 (d, J=8.3Hz, 1H),
3.90 (q, J=7.2Hz, 2H), 1.30 (t, J=7.2Hz, 3H).
13C NMR(101MHz,CDCl3)δ153.34,148.28,142.88,134.94,130.24,129.57,
129.29,127.55,126.01,125.91,123.29,122.32,119.51,109.53,106.03,36.14,13.64。
IR(KBr):3058,3033,2974,2929,2855,1712,1592,1491,1400,1276,1234,1192,
1082,1022,754,695,656cm-1。
MS(EI,m/z):405[M]+。
HRMS(ESI):Calcd.for C27H23N3ONa[M+Na]+:428.1733；found:428.1727.
The structure for inferring products therefrom according to data above is shown below：
Embodiment 2
0.5 mM of diphenylamines, 0.25 mM of N- ethyl isopropylamine, 0.05 mM of chlorine are added in schlenk pipes
Change cuprous, 0.5 mM of pyridine, 1.5 milliliters of isobutanols, at 80 DEG C, O2Under the conditions of (oxygen pressure used is an atmospheric pressure)
After stirring reaction 16 hours, stop heating and stirring, be cooled to room temperature, vacuum rotary steam removes solvent, then passes through column chromatography for separation
Purifying, target product is obtained, the volume ratio of column chromatography eluent used is 20:5:1 petroleum ether:Dichloromethane:Acetic acid second
Ester mixed solvent, yield 34%.
Respectively as shown in Figure 3 and Figure 4, structural characterization data are as follows for the hydrogen spectrogram and carbon spectrogram of products therefrom：
1H NMR(400MHz,CDCl3):δ 7.48-7.55 (m, 4H), 7.37 (t, J=6.7Hz, 1H), 7.23 (d, J=
7.4Hz, 3H), 7.09 (d, J=7.8Hz, 4H), 6.97 (d, J=7.5Hz, 4H), 6.79 (d, J=7.9Hz, 1H), 4.66
(dt, J=13.8,6.9Hz, 1H), 1.49 (d, J=6.9Hz, 6H).
13C NMR(101MHz,CDCl3):δ153.06,148.28,142.54,134.89,129.56,129.43,
129.29,127.59,126.11,123.29,122.32,119.12,109.43,107.38,45.42,20.23。
IR(KBr):3063,3042,2968,2929,2869,1712,1629,1593,1491,1388,1273,1236,
1176,752,695,660cm-1。
MS(EI,m/z):419[M]+。
HRMS(ESI):Calcd.for C28H25N3ONa[M+Na]+:442.1890；found:442.1888.
Infer that products therefrom obtains structure and is shown below according to data above：
Embodiment 3
0.5 mM of diphenylamines, 0.25 mM of triallylamine, 0.05 mM of trifluoro are added in schlenk pipes
Loprazolam copper, 0.5 mM of pyridine, 1.5 milliliters of isobutanols, at 100 DEG C, O2Under the conditions of (oxygen pressure used is one big
Air pressure) stirring reaction is after 12 hours, stopping heating and stirring, room temperature, vacuum rotary steam removing solvent are cooled to, then pass through column chromatography
Isolate and purify, obtain target product, the volume ratio of column chromatography eluent used is 20:5:1 petroleum ether:Dichloromethane:Second
Acetoacetic ester mixed solvent, yield 37%.
Respectively as shown in Figure 5 and Figure 6, structural characterization data are as follows for the hydrogen spectrogram and carbon spectrogram of products therefrom：
1H NMR(400MHz,CDCl3):δ7.61–7.47(m,4H),7.35–7.41(m,1H),7.19–7.27(m,4H),
7.02–7.11(m,4H),7.02–6.94(m,3H),6.85–6.80(m,2H),5.81–5.93(m,1H),5.12–5.22(m,
2H),4.52–4.41(m,2H)。
13C NMR(101MHz,CDCl3):δ153.42,148.21,142.92,134.93,131.73,130.39,
129.60,129.28,127.62,125.92,123.39,122.39,119.46,118.07,109.51,106.61,43.66。
IR(KBr):3066,3024,2959,2929,2852,1716,1635,1599,1489,1395,1273,1220,
1177,752,696,655cm-1。
MS(EI,m/z):417[M]+。
HRMS(ESI):Calcd.for C28H23N3ONa[M+Na]+:440.1733；found:440.1729.
Infer that products therefrom obtains structure and is shown below according to data above：
Embodiment 4
0.5 mM of 4- bromines diphenylamines, 0.25 mM of triethylamine, 0.05 mM of chlorination are added in schlenk pipes
Copper, 0.5 mM of pyridine, 0.5 mM of di-tert-butyl peroxide (DTBP), 1.5 milliliters of isobutanols, at 100 DEG C, O2Condition
Under (oxygen pressure used is an atmospheric pressure) stirring reaction after 12 hours, stop heating and stirring, be cooled to room temperature, decompression rotation
Solvent is evaporated off, then by column chromatographic isolation and purification, obtains target product, the volume ratio of column chromatography eluent used is 20:
5:1 petroleum ether:Dichloromethane:Ethyl acetate mixed solvent, yield 75%.
Respectively as shown in Figure 7 and Figure 8, structural characterization data are as follows for the hydrogen spectrogram and carbon spectrogram of products therefrom：
1H NMR(400MHz,CDCl3):δ 7.64 (d, J=7.2Hz, 2H), 7.44 (d, J=7.3Hz, 2H), 7.31 (d, J
=7.4Hz, 2H), 7.24 (d, J=7.4Hz, 2H), 7.07 (d, J=7.9Hz, 2H), 7.04-6.96 (m, 2H), 6.93 (d, J
=7.4Hz, 2H), 6.84 (s, 1H), 6.80 (d, J=8.4Hz, 1H), 3.89 (q, J=6.9Hz, 2H), 1.30 (t, J=
6.9Hz,3H)。
13C NMR(101MHz,CDCl3):δ153.02,147.67,147.37,142.64,133.93,132.76,
132.23,130.35,129.48,127.33,125.72,124.36,123.71,123.05,121.05,119.51,114.45,
109.52,106.05,36.22,13.62。
IR(KBr):3039,2959,2925,2852,1708,1638,1490,1403,1307,1232,1072,810,
748,700cm-1。
MS(EI,m/z):561[M]+。
HRMS(ESI):Calcd.for C27H21Br2N3ONa[M+Na]+:583.9944；found:583.9925.
Infer that products therefrom obtains structure and is shown below according to data above：
Embodiment 5
0.5 mM of diphenylamines, 0.25 mM of two n-hexylamine, 0.05 mM of copper chloride are added in schlenk pipes,
0.5 mM of pyridine, 1.5 milliliters of tert-pentyl alcohols, at 100 DEG C, O2Under the conditions of (oxygen pressure used is an atmospheric pressure) stirring it is anti-
After answering 12 hours, stop heating and stirring, be cooled to room temperature, vacuum rotary steam removes solvent, then by column chromatographic isolation and purification, obtains
To target product, the volume ratio of column chromatography eluent used is 20:5:1 petroleum ether:Dichloromethane:Ethyl acetate mixing is molten
Agent, yield 68%.
Respectively as shown in Figure 9 and Figure 10, structural characterization data are as follows for the hydrogen spectrogram and carbon spectrogram of products therefrom：
1H NMR(400MHz,CDCl3):δ 7.46-7.60 (m, 4H), 7.32-7.39 (m, 1H), 7.23 (t, J=7.9Hz,
4H), 7.08 (d, J=7.7Hz, 4H), 6.98 (dd, J=11.6,5.4Hz, 3H), 6.86 (d, J=1.8Hz, 1H), 6.80
(dd, J=8.4,2.0Hz, 1H), 3.82 (t, J=7.2Hz, 2H), 1.741.66 (m, 2H), 1.36-1.24 (m, 6H), 0.85
(t, J=6.9Hz, 3H).
13C NMR(101MHz,CDCl3):δ153.58,148.24,142.80,134.96,130.67,129.52,
129.26,127.47,125.90,125.85,123.25,122.29,119.39,109.45,106.20,41.37,31.51,
28.31,26.54,22.55,14.12。
IR(KBr):3066,3033,2953,2928,2857,1715,1626,1594,1490,1398,1370,1274,
1176,1092,753,695,657cm-1。
MS(EI,m/z):461[M]+。
HRMS(ESI):Calcd.for C31H31N3ONa[M+Na]+:484.2359；found:484.2363.
Infer that products therefrom obtains structure and is shown below according to data above：
Embodiment 6
0.5 mM of 4- methyldiphenylamine, 0.25 mM of diethylamine, 0.05 mM of chlorine are added in schlenk pipes
Change copper, 0.5 mM of pyridine, 1.5 milliliters of isobutanols, at 80 DEG C, O2Under the conditions of (oxygen pressure used is an atmospheric pressure) stir
After mixing reaction 24 hours, stop heating and stirring, be cooled to room temperature, vacuum rotary steam removes solvent, then pure by column chromatography for separation
Change, obtain target product, the volume ratio of column chromatography eluent used is 20:5:1 petroleum ether:Dichloromethane:Ethyl acetate
Mixed solvent, yield 59%.
Respectively as is illustrated by figs. 11 and 12, structural characterization data are as follows for the hydrogen spectrogram and carbon spectrogram of products therefrom：
1H NMR(400MHz,CDCl3):δ 7.43-7.39 (m, 2H), 7.30 (d, J=8.1Hz, 2H), 7.23-7.18 (m,
2H), 7.07-6.99 (m, 6H), 6.95-6.91 (m, 2H), 6.85 (d, J=1.8Hz, 1H), 6.78 (dd, J=8.4,1.9Hz,
1H), 3.89 (q, J=7.2Hz, 2H), 2.40 (s, 3H), 2.31 (s, 3H), 1.30 (t, J=7.2Hz, 3H).
13C NMR(101MHz,CDCl3):δ153.45,148.60,145.71,142.96,137.46,132.32,
132.28,130.17,130.15,129.97,129.18,126.04,125.83,124.07,122.55,121.70,119.14,
109.41,105.68,36.10,21.28,20.90,13.68。
IR(KBr):3030,2968,2926,2855,1714,1627,1594,1508,1492,1401,1294,1234,
811,750,696cm-1。
MS(EI,m/z):433[M]+。
HRMS(ESI):Calcd.for C29H27N3ONa[M+Na]+:456.2046；found:456.2047.
Infer that products therefrom obtains structure and is shown below according to data above：
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any Spirit Essences without departing from the present invention with made under principle change, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (9)
- A kind of 1. method of one-step synthesis 5- diarylamino benzimidazolone derivatives, it is characterised in that comprise the following steps：In the reactor, compound 1, compound 2, metallic catalyst, part, oxidant and solvent are added, at 25~130 DEG C 1~24h of stirring reaction, reaction are cooled to room temperature after terminating, vacuum rotary steam removes solvent and can obtain crude product, and crude product is through post Chromatographic purification obtains the 5- diarylaminos benzimidazolone derivatives；Described compound 1 refers to the compound with formula (1) structure；Described compound 2 refers to there is the two of formula (2) structure Level amine or tertiary amine, or its corresponding acid salt；Wherein, R1Represent the methyl of one or more substitutions on aromatic ring, phenyl, methoxyl group, nitro, itrile group, trifluoromethyl, ester group, Halogenic substituent or hydrogen；R2、R3、R4For alkyl that is identical or differing, substitute alkyl or hydrogen, but R2And R3It is asynchronously hydrogen.
- 2. a kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives according to claim 1, its feature It is：Described reactor is managed for schlenk.
- 3. a kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives according to claim 1, its feature It is：The mol ratio of the compound 1 and compound 2 is (1~20):1.
- 4. a kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives according to claim 1, its feature It is：Described metallic catalyst is copper acetate, copper sulphate, stannous chloride, copper chloride, copper fluoride, copper fluoride, iodate Asia Mixing more than one or both of copper, cuprous bromide, copper bromide, trifluoromethayl sulfonic acid copper.
- 5. a kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives according to claim 1, its feature It is：Described part is containing n-donor ligand.
- 6. a kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives according to claim 5, its feature It is：Described containing n-donor ligand is pyridine or pyridine derivate.
- 7. a kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives according to claim 1, its feature It is：Described oxidant is metal oxide, peroxide, the acid with oxidisability, silver salt and one kind in oxygen or two The mixing of the kind above, the pressure of the oxygen is 1~30 atmospheric pressure.
- 8. a kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives according to claim 1, its feature It is：Described solvent is acetonitrile, tetrahydrofuran, ethanol, tert-pentyl alcohol, isopropanol, isobutanol, N,N-dimethylformamide, two Mixing more than one or both of methyl sulfoxide, toluene, paraxylene, first alcohol and water.
- 9. a kind of method of one-step synthesis 5- diarylamino benzimidazolone derivatives according to claim 1, its feature It is：Described column chromatography purification eluent used is petroleum ether:Dichloromethane:The volume ratio of ethyl acetate for (0.5~ 50):(0~20):1 mixed solvent.
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| CN110790670A (en) * | 2019-08-27 | 2020-02-14 | 浙江工业大学 | Synthesis method of photocatalytic tertiary amine compound |
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| CN110790670A (en) * | 2019-08-27 | 2020-02-14 | 浙江工业大学 | Synthesis method of photocatalytic tertiary amine compound |
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