CN109438318A - The synthetic method of 3- (hetero) aryl indole and its derivative - Google Patents
The synthetic method of 3- (hetero) aryl indole and its derivative Download PDFInfo
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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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Abstract
The invention mainly relates to the synthetic methods of a kind of 3- (hetero) aryl indole and its derivative, the synthetic method includes the following steps: under the action of Lewis acid and S powder, the stirring of Benzazole compounds, cyclohexanone analog compound and organic solvent Hybrid Heating is reacted, then purifying obtains 3- (hetero) aryl indole and its derivative.The present invention has the advantage that the present invention using N- methyl indol and cyclohexanone as raw material, under the action of Lewis acid and S powder, synthesizes 3- (hetero) aryl indole and its derivative, raw material is simple, and synthesis cost is low；For synthetic method of the present invention without using transition metal-catalyzed, the synthesis for 3- (hetero) aryl indole class compound provides a new path；Synthetic method of the present invention has the characteristics that regioselectivity is high, reaction condition is simple.
Description
[technical field]
The invention belongs to the conjunctions of organic compound synthesis technical field more particularly to a kind of 3- (hetero) aryl indole and its derivative
At method.
[background technique]
(hetero) aryl indole class compound is a kind of very important indole derivatives, is widely present in many natural products and medicine
In object molecule.Because (hetero) aryl indole class compound has unique pharmacological activity, the synthesis of (hetero) aryl indole and its derivative
Research is constantly subjected to the close attention of chemists.
In the related technology, the synthetic method about 3- (hetero) aryl indole and its derivative, mainly using transition metal-catalyzed.
[summary of the invention]
The object of the present invention is to provide the synthetic method of a kind of 3- (hetero) aryl indole and its derivative, simple with raw material,
Regioselectivity is high, reaction condition is simple, without using it is transition metal-catalyzed the features such as.
In order to achieve the above object, technical scheme is as follows:
The synthetic method of a kind of 3- (hetero) aryl indole and its derivative, the synthetic method include the following steps:
Under the action of Lewis acid and S powder, Benzazole compounds, cyclohexanone analog compound and organic solvent are mixed and added
Thermal agitation is reacted, and then purifying obtains 3- (hetero) aryl indole and its derivative shown in formula I,
Wherein,
R1Selected from hydrogen atom, methyl, halogen radical and alkoxy；
R2Selected from hydrogen atom, C1-C5Saturated alkane straight chain, C1-C5Saturated alkane branch and halogen radical；
R3Selected from hydrogen atom, methyl and benzyl.
Preferably, the organic solvent be selected from dimethyl sulfoxide, n,N-Dimethylformamide, n,N-dimethylacetamide,
N-Methyl pyrrolidone, toluene, dimethylbenzene, mesitylene, chlorobenzene, dichloro-benzenes, 1,4- dioxane, n-hexane, hexamethylene.
Preferably, the organic solvent is n,N-Dimethylformamide.
Preferably, the Lewis acid is selected from BF3·Et2O、AlCl3、Zn(CF3SO3)2、CF3SO3H、CH3SO3H。
Preferably, the Benzazole compounds, the cyclohexanone cyclics, the S powder and the Lewis are sour rubs
You are than being 1:(0.5-2.5): (1-5): (0.2-2), reaction temperature are 130-160 DEG C, reaction atmosphere be oxygen percentage be 0~
50% gas, when reaction a length of 1-36h.
Preferably, the Benzazole compounds are selected from C9-C16Class indoles, general formula II are as follows:
Wherein,
R1Selected from hydrogen atom, methyl, halogen radical, alkoxy；
R3Selected from hydrogen atom, methyl, benzyl.
Preferably, the Benzazole compounds are selected from 1- benzylindole, 1- methyl indol, 2- methyl-1-methyl indol, 5-
Methyl-1-methyl indol, the fluoro- 1- methyl indol of 5-, the chloro- 1- methyl indol of 5-, 5- methoxyl group-1- methyl indol, 5- benzyloxy-
1- methyl indol, 6- methyl-1-methyl indol, the fluoro- 1- methyl indol of 6-, the chloro- 1- methyl indol of 6-, 7- methyl-1-methyl Yin
Diindyl and the chloro- 1- methyl indol of 7-.
Preferably, the general formula III of the cyclohexanone analog compound is as follows:
Wherein, R2Selected from hydrogen atom, C1-C5Saturated alkane straight chain, C1-C5Saturated alkane branch, halogen radical.
Preferably, the cyclohexanone analog compound be selected from 4- methyl cyclohexanone, 4- ethyl cyclohexanone, 4- propylcyclohexanone,
4- n-pentyl cyclohexanone, 4- t-pentylcyclohexanone, 4- tert-butyl cyclohexanone, 3- methyl cyclohexanone and 2- methyl cyclohexanone.
The present invention has the advantage that
1, the present invention is using N- methyl indol and cyclohexanone as raw material, under the action of Lewis acid and S powder, synthesizes 3- aryl
Indoles and its derivative, raw material is simple, and synthesis cost is low；
2, without using transition metal-catalyzed, the synthesis for 3- (hetero) aryl indole class compound provides synthetic method of the present invention
One new path；
3, synthetic method of the present invention has the characteristics that regioselectivity is high, reaction condition is simple.
[Detailed description of the invention]
To describe the technical solutions in the embodiments of the present invention more clearly, make required in being described below to embodiment
Attached drawing is briefly described, in which:
Fig. 1-1 is the nucleus magnetic hydrogen spectrum figure of 1 product of embodiment；
Fig. 1-2 is the nuclear-magnetism carbon spectrogram of 1 product of embodiment；
Fig. 2-1 is the nucleus magnetic hydrogen spectrum figure of 2 product of embodiment；
Fig. 2-2 is the nuclear-magnetism carbon spectrogram of 2 product of embodiment；
Fig. 3-1 is the nucleus magnetic hydrogen spectrum figure of 3 product of embodiment；
Fig. 3-2 is the nuclear-magnetism carbon spectrogram of 3 product of embodiment；
Fig. 4-1 is the nucleus magnetic hydrogen spectrum figure of 4 product of embodiment；
Fig. 4-2 is the nuclear-magnetism carbon spectrogram of 4 product of embodiment；
Fig. 5-1 is the nucleus magnetic hydrogen spectrum figure of 5 product of embodiment；
Fig. 5-2 is the nuclear-magnetism carbon spectrogram of 5 product of embodiment；
Fig. 6-1 is the nucleus magnetic hydrogen spectrum figure of 6 product of embodiment；
Fig. 6-2 is the nuclear-magnetism carbon spectrogram of 6 product of embodiment；
Fig. 7-1 is the nucleus magnetic hydrogen spectrum figure of 7 product of embodiment；
Fig. 7-2 is the nuclear-magnetism carbon spectrogram of 7 product of embodiment；
Fig. 8-1 is the nucleus magnetic hydrogen spectrum figure of 8 product of embodiment；
Fig. 8-2 is the nuclear-magnetism carbon spectrogram of 8 product of embodiment；
Fig. 9-1 is the nucleus magnetic hydrogen spectrum figure of 9 product of embodiment；
Fig. 9-2 is the nuclear-magnetism carbon spectrogram of 9 product of embodiment；
Figure 10-1 is the nucleus magnetic hydrogen spectrum figure of 10 product of embodiment；
Figure 10-2 is the nuclear-magnetism carbon spectrogram of 10 product of embodiment.
[specific embodiment]
Technical solution of the present invention is clearly and completely described below in conjunction with attached drawing, it is clear that described implementation
Example is a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, ordinary skill
Personnel's every other embodiment obtained without making creative work, shall fall within the protection scope of the present invention.
The present invention provides a kind of 3- (hetero) aryl indole and its derivative synthesizing process, which includes the following steps:
Under the action of Lewis acid and S powder, Benzazole compounds, cyclohexanone analog compound and organic solvent are mixed and added
Thermal agitation is reacted, and then purifying obtains 3- (hetero) aryl indole and its derivative shown in formula I；
Wherein,
R1Selected from hydrogen atom, methyl, halogen radical and alkoxy；
R2Selected from hydrogen atom, C1-C5Saturated alkane straight chain, C1-C5Saturated alkane branch and halogen radical；
R3Selected from hydrogen atom, methyl and benzyl.
Wherein, the organic solvent is selected from dimethyl sulfoxide, n,N-Dimethylformamide (DMF), N, N- dimethylacetamide
Amine (DMAC), N-Methyl pyrrolidone (NMP), toluene, dimethylbenzene, mesitylene, chlorobenzene, dichloro-benzenes, 1,4- dioxane, just
Hexane, hexamethylene, in a preferred embodiment of the invention, the organic solvent are n,N-Dimethylformamide.
The Lewis acid is selected from BF3·Et2O、AlCl3、Zn(CF3SO3)2、CF3SO3H、CH3SO3H, of the invention excellent
It selects in embodiment, the Lewis acid is BF3·Et2O。
The Benzazole compounds, the cyclohexanone cyclics, the S powder and Lewis acid molar ratio be
1:(0.5-2.5): (1-5): (0.2-2), reaction temperature are 130-160 DEG C, and reaction atmosphere is that oxygen percentage is 0~50%
Gas, when reaction a length of 1-36h, in a preferred embodiment of the invention, molar ratio 1:2.5:4:1, reaction temperature 150
DEG C, reaction atmosphere is the air that oxygen percentage is 0~29%, when reaction a length of 16h.
The Benzazole compounds are selected from C9-C16Class indoles, general formula II are as follows:
Wherein,
R1Selected from hydrogen atom, methyl, halogen radical, alkoxy；
R3Selected from hydrogen atom, methyl, benzyl.
The Benzazole compounds are selected from 1- benzylindole, 1- methyl indol, 2- methyl-1-methyl indol, 5- methyl-1-
Methyl indol, the fluoro- 1- methyl indol of 5-, the chloro- 1- methyl indol of 5-, 5- methoxyl group -1- methyl indol, 5- benzyloxy -1- methyl
Indoles, 6- methyl-1-methyl indol, the fluoro- 1- methyl indol of 6-, the chloro- 1- methyl indol of 6-, 7- methyl-1-methyl indol and 7-
Chloro- 1- methyl indol.
The general formula III of the cyclohexanone analog compound is as follows:
Wherein, R2Selected from hydrogen atom, C1-C5Saturated alkane straight chain, C1-C5Saturated alkane branch, halogen radical.
The cyclohexanone analog compound is selected from 4- methyl cyclohexanone, 4- ethyl cyclohexanone, 4- propylcyclohexanone, 4- n-pentyl
Cyclohexanone, 4- t-pentylcyclohexanone, 4- tert-butyl cyclohexanone, 3- methyl cyclohexanone and 2- methyl cyclohexanone.
The synthetic reaction plant process for the compound that the present invention synthesizes is as follows:
Wherein, DMF is n,N-Dimethylformamide, and air is air, and T is reaction temperature, and t is reaction duration.
It can be concluded that the compound that the present invention synthesizes is using N- methyl indol and cyclohexanone as raw material, in Lewis acid and S
Under the action of powder, the 3- (hetero) aryl indole and its derivative of synthesis.
In short, the compound that the present invention synthesizes has the spies such as reaction raw materials are simple and easy to get, regioselectivity is high, condition is simple
A series of 3- (hetero) aryl indole class compounds of point, synthesis have certain bioactivity and pharmacological activity.
The 3- (hetero) aryl indole and its derivative synthesis side that the present invention will be described in detail provides are come with embodiment 1-10 below
Yield of method under the conditions of differential responses, referring in particular to table 1.
Table 1: reaction substrate, reaction condition and the yield of embodiment 1-10
The nuclear magnetic data of the product of embodiment 1-10 are as follows:
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 1 product of embodiment are respectively such as Fig. 1-1 and 1-2, the nuclear-magnetism of 1 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.93 (d, J=8.0Hz, 1H), 7.64 (d, J=7.1Hz, 2H),
7.42 (t, J=7.7Hz, 2H), 7.35 (d, J=8.2Hz, 1H), 7.29-7.22 (m, 3H), 7.18 (t, J=7.5Hz, 1H),
3.82(s,3H).13C NMR(100MHz,Chloroform-d)δ137.5,135.7,128.8,127.4,126.6,126.2,
125.8,122.0,120.0,119.9,116.7,109.6,33.0.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 2 product of embodiment are respectively such as Fig. 2-1 and 2-2, the nuclear-magnetism of 2 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.92 (d, J=8.0Hz, 1H), 7.55 (d, J=8.1Hz, 2H),
7.35 (d, J=8.2Hz, 1H), 7.26 (dd, J=13.0,7.8Hz, 3H), 7.18 (d, J=7.0Hz, 2H), 3.82 (s, 3H),
2.39(s,3H).13C NMR(100MHz,Chloroform-d)δ137.5,135.3,132.7,129.5,127.3,126.3,
126.3,121.9,120.0,119.8,116.7,109.5,32.9,21.2.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 3 product of embodiment are respectively such as Fig. 3-1 and 3-2, the nuclear-magnetism of 3 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.89 (d, J=8.0Hz, 1H), 7.51 (d, J=8.0Hz, 2H),
7.30 (d, J=8.2Hz, 1H), 7.25-7.18 (m, 3H), 7.13 (d, J=8.2Hz, 2H), 3.77 (s, 3H), 2.62-2.56
(m, 2H), 1.64-1.59 (m, 2H), 1.34-1.28 (m, 4H), 0.86 (t, J=6.2Hz, 3H)13C NMR(100MHz,
Chloroform-d)δ140.5,137.5,132.9,128.8,127.2,126.3,126.3,121.9,120.0,119.7,
116.8,109.5,35.7,32.9,31.7,31.3,22.6,14.1.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 4 product of embodiment are respectively such as Fig. 4-1 and 4-2, the nuclear-magnetism of 4 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.88 (d, J=8.0Hz, 1H), 7.53 (d, J=8.5Hz, 2H),
(7.40 d, J=8.5Hz, 2H), 7.28 (d, J=8.2Hz, 1H), 7.22-7.17 (m, 1H), 7.14-7.09 (m, 2H), 3.75
(s,3H),1.31(s,9H).13C NMR(100MHz,Chloroform-d)δ148.6,137.5,132.9,127.1,126.4,
126.4,125.7,121.9,120.2,119.8,116.68,109.5,34.6,32.9,31.5.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 5 product of embodiment are respectively such as Fig. 5-1 and 5-2, the nuclear-magnetism of 5 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.89 (d, J=8.0Hz, 1H), 7.41 (d, J=7.7Hz, 2H),
7.28 (q, J=7.9Hz, 2H), 7.21 (dd, J=15.7,8.3Hz, 1H), 7.15 (d, J=12.0Hz, 2H), 7.03 (d, J=
7.6Hz,1H),3.77(s,3H),2.37(s,3H).13C NMR(100MHz,Chloroform-d)δ138.3,137.5,
135.6,128.7,128.1,126.6,126.5,126.2,124.5,120.0,120.0,119.8 116.8,109.5,32.9,
21.7.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 6 product of embodiment are respectively such as Fig. 6-1 and 6-2, the nuclear-magnetism of 6 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.53 (d, J=7.9Hz, 1H), 7.45-7.36 (m, 2H), 7.35-
7.31 (m, 1H), 7.30-7.24 (m, 3H), 7.14 (t, J=7.5Hz, 1H), 7.06 (s, 1H), 3.86 (s, 3H), 2.35 (s,
3H).13C NMR(100MHz,Chloroform-d)δ136.7,134.6,130.9,130.4,127.6,127.6,127.5,
126.6,125.6,121.7,120.3,119.4,116.0,109.3,32.9,20.9.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 7 product of embodiment are respectively such as Fig. 7-1 and 7-2, the nuclear-magnetism of 7 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.64 (s, 1H), 7.48 (dd, J=8.1,1.8Hz, 2H), 7.19
(d, J=8.5Hz, 3H), 7.09 (s, 1H), 7.04 (d, J=8.3Hz, 1H), 3.74 (s, 3H), 2.42 (s, 3H), 2.34 (s,
3H).13C NMR(100MHz,Chloroform-d)δ135.9,135.2,132.9,129.4,129.0,127.3,126.4,
126.4,123.5,119.6,116.1,109.2,32.9,21.6,21.2.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 8 product of embodiment are respectively such as Fig. 8-1 and 8-2, the nuclear-magnetism of 8 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.75 (d, J=8.5Hz, 1H), 7.45 (d, J=8.0Hz, 2H),
(7.29 d, J=1.5Hz, 1H), 7.20 (d, J=6.4Hz, 2H), 7.13 (s, 1H), 7.08 (dd, J=8.5,1.7Hz, 1H)
.3.79(s,3H),2.40(s,3H).13C NMR(100MHz,Chloroform-d)δ137.9,135.7,132.1,129.5,
128.0,127.2,126.8,124.8,120.9,120.4,117.0,109.5,33.0,21.2.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 9 product of embodiment are respectively such as Fig. 9-1 and 9-2, the nuclear-magnetism of 9 product of embodiment
Data are as follows:
1H NMR (400MHz, Chloroform-d) δ 7.82 (d, J=7.9Hz, 1H), 7.60 (d, J=8.0Hz, 2H),
7.33 (d, J=7.4Hz, 2H), 7.16-7.09 (m, 2H), 7.04 (d, J=7.0Hz, 1H), 4.18 (s, 3H), 2.88 (s,
3H),2.48(s,3H).13C NMR(100MHz,Chloroform-d)δ136.1,135.4,132.7,129.4,128.1,
127.6,127.4,124.6,121.5,120.0,118.1,116.6,36.9,21.2,19.9.
The nucleus magnetic hydrogen spectrum figure and nuclear-magnetism carbon spectrogram of 10 product of embodiment respectively such as Figure 10-1 and 10-2,10 product of embodiment
Nuclear magnetic data is as follows:
1H NMR (400MHz, Chloroform-d) δ 7.70 (d, J=8.0Hz, 1H), 7.42 (d, J=8.0Hz, 2H),
7.19 (d, J=6.4Hz, 2H), 7.12 (d, J=7.5Hz, 1H), 7.05 (s, 1H), 6.97 (t, J=7.8Hz, 1H), 4.13
(s,3H),2.34(s,3H).
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And thus amplify out it is obvious variation or
It changes still within the protection scope of the invention.
Claims (9)
1. the synthetic method of a kind of 3- (hetero) aryl indole and its derivative, which is characterized in that the synthetic method includes the following steps:
Under the action of Lewis acid and S powder, Benzazole compounds, cyclohexanone analog compound and organic solvent Hybrid Heating are stirred
It mixes and is reacted, then purifying obtains 3- (hetero) aryl indole and its derivative shown in formula I,
Wherein,
R1Selected from hydrogen atom, methyl, halogen radical and alkoxy；
R2Selected from hydrogen atom, C1-C5Saturated alkane straight chain, C1-C5Saturated alkane branch and halogen radical；
R3Selected from hydrogen atom, methyl and benzyl.
2. the synthetic method of 3- (hetero) aryl indole according to claim 1 and its derivative, which is characterized in that described organic molten
Agent is selected from dimethyl sulfoxide, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, N-Methyl pyrrolidone, toluene, diformazan
Benzene, mesitylene, chlorobenzene, dichloro-benzenes, 1,4- dioxane, n-hexane, hexamethylene.
3. the synthetic method of 3- (hetero) aryl indole according to claim 2 and its derivative, which is characterized in that described organic molten
Agent is N,N-dimethylformamide.
4. the synthetic method of 3- (hetero) aryl indole according to claim 1 and its derivative, which is characterized in that the Lewis
Acid is selected from BF3·Et2O、AlCl3、Zn(CF3SO3)2、CF3SO3H、CH3SO3H。
5. the synthetic method of 3- (hetero) aryl indole according to claim 1 and its derivative, which is characterized in that the indoles
Compound, the cyclohexanone cyclics, the S powder and Lewis acid molar ratio be 1:(0.5-2.5): (1-5):
(0.2-2), reaction temperature are 130-160 DEG C, and reaction atmosphere is the gas that oxygen percentage is 0-50%, when reaction a length of 1-
36h。
6. the synthetic method of 3- (hetero) aryl indole according to claim 1 and its derivative, which is characterized in that the indoles
Compound is selected from C9-C16Class indoles, general formula II are as follows:
Wherein,
R1Selected from hydrogen atom, methyl, halogen radical, alkoxy；
R3Selected from hydrogen atom, methyl, benzyl.
7. the synthetic method of 3- (hetero) aryl indole according to claim 6 and its derivative, which is characterized in that the indoles
Compound is selected from 1- benzylindole, 1- methyl indol, 2- methyl-1-methyl indol, 5- methyl-1-methyl indol, the fluoro- 1- first of 5-
Base indoles, the chloro- 1- methyl indol of 5-, 5- methoxyl group-1- methyl indol, 5- benzyloxy-1- methyl indol, 6- methyl-1-methyl
Indoles, the fluoro- 1- methyl indol of 6-, the chloro- 1- methyl indol of 6-, 7- methyl-1-methyl indol and the chloro- 1- methyl indol of 7-.
8. the synthetic method of 3- (hetero) aryl indole according to claim 1 and its derivative, which is characterized in that the cyclohexanone
The general formula III of class compound is as follows:
Wherein, R2Selected from hydrogen atom, C1-C5Saturated alkane straight chain, C1-C5Saturated alkane branch, halogen radical.
9. the synthetic method of 3- (hetero) aryl indole according to claim 8 and its derivative, which is characterized in that the cyclohexanone
Class compound is selected from 4- methyl cyclohexanone, 4- ethyl cyclohexanone, 4- propylcyclohexanone, 4- n-pentyl cyclohexanone, 4- tertiary pentyl ring
Hexanone, 4- tert-butyl cyclohexanone, 3- methyl cyclohexanone and 2- methyl cyclohexanone.
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| CN109438318B (en) | 2022-05-03 |
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