CN112592344A - Indolo [2,3-b ] indole derivative and synthetic method thereof - Google Patents

Indolo [2,3-b ] indole derivative and synthetic method thereof Download PDF

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CN112592344A
CN112592344A CN202011293410.1A CN202011293410A CN112592344A CN 112592344 A CN112592344 A CN 112592344A CN 202011293410 A CN202011293410 A CN 202011293410A CN 112592344 A CN112592344 A CN 112592344A
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indole
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cyclohexanone
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CN112592344B (en
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邓国军
姜平宇
陈善平
黄华文
肖福红
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Xiangtan University
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract

The invention mainly relates to an indolo [2,3-b ] indole and a derivative thereof and a synthesis method thereof, wherein a technical scheme that a 2- (3-indolyl) cyclohexanone compound and an aniline compound are converted into a polysubstituted indolo [2,3-b ] indole derivative only under the action of an iodine reagent and an organic solvent without using a metal catalyst during synthesis is provided; the method solves the problems that the existing synthesis method of the functionalized indolo [2,3-b ] indole compound has complex synthesis steps, can be completed by adopting a multi-step synthesis process, and also needs a metal catalyst or peroxide and raw materials are difficult to prepare; it maintains atom economy to the utmost extent; the method also has the characteristics of simple reaction system, mild reaction conditions, less reaction equipment, simple and convenient experimental operation, wide material sources, high yield, easy expansion of users and applications, higher product utilization value, predictable market commercialization prospect and the like.

Description

Indolo [2,3 ]-b]Indole derivatives and synthesis method thereof
Technical Field
The invention relates to an indolo [2,3 ]-b]Indole derivatives and a synthetic method thereof, belonging to the technical field of organic synthesis.
Background
The indoindole is an important skeleton structure of a plurality of medicines, medicine intermediates, organic electrochemical devices and organic luminescent materials, and is widely applied to the fields of organic luminescent semiconductors, medicines and photoelectric materials. Therefore, methods for synthesizing indolo-indole derivatives have been gaining wide attention. The existing method for synthesizing the compounds has the defects that the synthesis steps are complex, a multi-step synthesis process is needed for completion, a transition metal catalyst and a metal oxidant with chemical equivalent are needed to be added, and a starting raw material with relatively high activity is needed to be used.
Disclosure of Invention
In view of the above, it is an object of the present invention to provide an indolo [2,3 ]-b]Indole and derivatives thereof have stable molecular structure and excellent chemical properties, are important molecular blocks, are compound fragments containing physiological activity and pharmacological activity, and have certain photoelectric property, biological activity and pharmaceutical activity.
It is still another object of the present invention to provide an indolo [2,3 ]-b]The method for preparing indole, the derivative and the derivative has the advantages of scientific and reasonable process, easy operation, few reaction steps, simple required equipment, cheap and easily-obtained raw materials, no need of using a metal catalyst and a metal oxidant in the reaction, capability of keeping atom economy to a large extent in the reaction, low input and high output, and easiness in industrial production and popularization.
To achieve the above object, indolo [2,3 ]-b]Indoles and derivatives thereof having the general formula:
Figure 458052DEST_PATH_IMAGE001
Ⅰ
wherein
R1Selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a benzyl group; a substituted or unsubstituted C6-C20 aryl group;
R2selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogen; an alkoxy group; an ester group;
R3selected from hydrogen atoms; a linear chain of C1-C10;
R4selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogen; an alkoxy group; an ester group; a nitro group; a cyano group; a trifluoromethyl group; a trifluoromethoxy group; acetyl; substituted or unsubstituted C6-C14 aryl.
The invention also provides an indolo [2,3 ]-b]The method for preparing indole derivatives is characterized in that a catalyst, an oxidant, aniline compounds, 2- (3-indolyl) cyclohexanone and derivatives thereof and an organic solvent are mixed and heated for reaction, and finally the product is obtained after purification.
In the synthesis method, the catalyst is an iodine reagent selected from the following components: one or more of trimethyl sulfoxide iodide, ammonium iodide, potassium iodide, elemental iodine, iodine chloride, iodobenzene, diethyl iodobenzene, N-iodosuccinimide and diiodo pentoxide; the oxidant is selected from: one or more of dimethyl sulfoxide, methyl phenyl sulfone, methyl benzyl sulfone, TBHP, oxygen, diiodo pentoxide, sodium periodate, potassium persulfate, etc.; the organic solvent is one or more of toluene, xylene, trimethylbenzene, benzotrifluoride, ethylbenzene, chlorobenzene, o-dichlorobenzene, anisole, 1, 4-dioxane, dimethyl sulfoxide, N-methyl pyrrolidone and the like; the mol ratio of the 2- (3-indolyl) cyclohexanone compound to the aniline compound to the catalyst to the oxidant is 1: 0.5-5.0: 0.1-1.0: 0.1 to 10; meanwhile, the reaction temperature is 100-200 ℃.
The synthesis method of the invention is that the general formula of the 2- (3-indolyl) cyclohexanone compound is formula II:
Figure 213518DEST_PATH_IMAGE002
Ⅱ
wherein
R1Selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a benzyl group; a substituted or unsubstituted C6-C20 aryl group;
R2selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogen; an alkoxy group; an ester group; a substituted or unsubstituted C6-C20 aryl group;
R3selected from hydrogen atoms; C1-C10 Linear chain
In the method, the 2- (3-indolyl) cyclohexanone compound in the formula II is selected from 2- (3-indolyl) cyclohexanone; 2- (3- (1-methyl) -indole) cyclohexanone; 2- (3- (1-ethyl) -indole); 2- (3- (1-pentenyl) -indole); 2- (3- (1-isopropyl) -indole); 2- (3- (1-cyclohexyl) -indole); 2- (3- (1-benzyl) -indole); 2- (3- (1, 4 dimethyl) -indole) cyclohexanone; 2- (3- (1, 5 dimethyl) -indole) cyclohexanone; 2- (3- (1, 6 dimethyl) -indole) cyclohexanone; 2- (3- (1, 7 dimethyl) -indole) cyclohexanone; 2- (3- (1-methyl-5 fluoro) -indole) cyclohexanone; 2- (3- (1-methyl-5-bromo) -indole) cyclohexanone; 2- (3- (1-methyl-6-carboxylic acid methyl ester) -indole) cyclohexanone; 2- (3- (1-methyl-6-chloro) -indole) cyclohexanone; 2- (3- (1-methyl) -indole) -2-methylcyclohexanone; 2- (3- (1-methyl) -indole) -4-methylcyclohexanone.
According to the method, the general formula of the aniline compound is shown as a formula III:
Figure 806174DEST_PATH_IMAGE003
Ⅲ
wherein
R4Selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a carboxyl group; an ester group; an alkoxy group; halogen; a trifluoromethyl group; a substituted or unsubstituted C6-C20 aryl group;
according to the synthesis method, the aniline compound is selected from aniline; 2-methylaniline; 2-phenylaniline; 2-chloroaniline; 3-methylaniline; 3-tert-butylaniline; 3-fluoroaniline; 3-chloroaniline; 3-bromoaniline; 3-trifluoromethylaniline; 3-trifluoromethoxyaniline; 3-nitroaniline; 3-carboxylic acid methyl ester aniline; 3-cyanoaniline; 4-methylaniline, 4-phenylaniline; 4-fluoroaniline; 4-chloroaniline; 4-chloroaniline; 4-bromoaniline; 4-methoxyaniline; 4-trifluoromethoxyaniline; 4-nitroaniline; 4-acetanilide; 3, 3-dibromoaniline, 2-naphthylamine; 2-anthracenamine; 5-amino-2, 2-difluoro-1, 3-benzodioxazole; 1, 3-benzothiazol-5-amine.
The technical scheme of the invention has the following advantages:
the present invention is a compound of indolo [2,3 ]-b]Indole derivatives thereof and processes for their synthesis2- (3-indolyl) cyclohexanone, aniline and derivatives thereof are converted into indolo [2, 3-indolyl) cyclohexanone, aniline and derivatives thereof by using one or more of toluene, xylene, trimethylbenzene, trifluorotoluene, ethylbenzene, chlorobenzene, o-dichlorobenzene, anisole, 1, 4-dioxane, dimethyl sulfoxide, N-methylpyrrolidone and the like as organic reaction solvents under the action of iodine only by using a metal catalyst and a metal oxidant-b]Indole and derivatives thereof; it overcomes the existing indolo [2,3 ]-b]The synthesis method of the indole compound has the defects that a metal catalyst and a metal oxidant are required to be used or a starting raw material with relatively high activity is required to be used; it maintains atom economy to a large extent; it has stable molecular structure, excellent chemical property, molecular blocks and compound fragments containing rich biological activity and pharmacological activity; the method also has the characteristics of simple reaction system, less reaction equipment, simple and convenient operation, cheap and easily obtained raw materials, easy expansion of application, higher product utilization value, expected market commercialization prospect and the like.
The present invention will be described in further detail with reference to the accompanying drawings and examples.
Drawings
In order to demonstrate the products of the invention, the invention provides nuclear magnetic hydrogen and carbon spectra of some of the examples.
FIG. 1-1 nuclear magnetic hydrogen spectrum of the product of example 1.
FIGS. 1-2 nuclear magnetic carbon spectrum of the product of example 1.
FIG. 2-1 nuclear magnetic hydrogen spectrum of the product of example 2.
Figure 2-2 nuclear magnetic carbon spectrum of the product of example 2.
FIG. 3-1 nuclear magnetic hydrogen spectrum of the product of example 3.
Figure 3-2 nuclear magnetic carbon spectrum of the product of example 3.
FIG. 4-1 nuclear magnetic hydrogen spectrum of the product of example 4.
Figure 4-2 nuclear magnetic carbon spectrum of the product of example 4.
FIG. 5-1 nuclear magnetic hydrogen spectrum of the product of example 5.
Figure 5-2 nuclear magnetic carbon spectrum of the product of example 5.
FIG. 6-1 nuclear magnetic hydrogen spectrum of the product of example 6.
Figure 6-2 nuclear magnetic carbon spectrum of the product of example 6.
FIG. 7-1 nuclear magnetic hydrogen spectrum of the product of example 7.
Figure 7-2 nuclear magnetic carbon spectrum of the product of example 7.
FIG. 8-1 nuclear magnetic hydrogen spectrum of the product of example 8.
Figure 8-2 nuclear magnetic carbon spectrum of the product of example 8.
FIG. 9-1 nuclear magnetic hydrogen spectrum of the product of example 9.
Figure 9-2 nuclear magnetic carbon spectrum of the product of example 9.
FIG. 10-1 nuclear magnetic hydrogen spectrum of the product of example 10.
FIG. 10-2 nuclear magnetic carbon spectrum of the product of example 10.
FIG. 11-1 nuclear magnetic hydrogen spectrum of the product of example 11.
FIG. 11-2 nuclear magnetic carbon spectrum of the product of example 11.
FIG. 12-1 nuclear magnetic hydrogen spectrum of the product of example 12.
FIG. 12-2 nuclear magnetic carbon spectrum of the product of example 12.
FIG. 13-1 nuclear magnetic hydrogen spectrum of the product of example 13.
FIG. 13-2 nuclear magnetic carbon spectrum of the product of example 13.
FIG. 14-1 nuclear magnetic hydrogen spectrum of the product of example 14.
FIG. 14-2 nuclear magnetic carbon spectrum of the product of example 14.
FIG. 15-1 nuclear magnetic hydrogen spectrum of the product of example 15.
Figure 15-2 nuclear magnetic carbon spectrum of the product of example 15.
FIG. 16-1 nuclear magnetic hydrogen spectrum of the product of example 16.
Figure 16-2 nuclear magnetic carbon spectrum of the product of example 16.
FIG. 17-1 nuclear magnetic hydrogen spectrum of the product of example 17.
Figure 17-2 nuclear magnetic carbon spectrum of the product of example 17.
FIG. 18-1 nuclear magnetic hydrogen spectrum of the product of example 18.
Figure 18-2 nuclear magnetic carbon spectrum of the product of example 18.
FIG. 19-1 nuclear magnetic hydrogen spectrum of the product of example 19.
Figure 19-2 nuclear magnetic carbon spectrum of the product of example 19.
FIG. 20-1 nuclear magnetic hydrogen spectrum of the product of example 20.
Figure 20-2 nuclear magnetic carbon spectrum of the product of example 20.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the accompanying drawings, and it should be understood that the described embodiments are some, but not all embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In addition, the technical features involved in the different embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
Indolo [2,3-b ] indoles and derivatives thereof having the general formula:
Figure 372415DEST_PATH_IMAGE004
Ⅰ
wherein the content of the first and second substances,
R1selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a benzyl group; a substituted or unsubstituted C6-C20 aryl group;
R2selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogen; an alkoxy group; an ester group;
R3selected from hydrogen atoms; a linear chain of C1-C10;
R4selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogen; an alkoxy group; an ester group; a nitro group; a cyano group; a trifluoromethyl group; a trifluoromethoxy group; acetyl; substituted or unsubstituted C6-C14 aryl
The invention also provides an indolo [2,3 ]-b]A process for producing indole derivatives characterized by reacting a catalyst, an oxidizing agent and an anilineMixing the compound, 2- (3-indolyl) cyclohexanone and its derivative and organic solvent, heating to react, and final purifying to obtain the product.
In the synthesis method, the catalyst is an iodine reagent selected from the following components: one or more of trimethyl sulfoxide iodide, ammonium iodide, potassium iodide, elemental iodine, iodine chloride, iodobenzene, diethyl iodobenzene, N-iodosuccinimide and diiodo pentoxide; the oxidant is selected from: one or more of dimethyl sulfoxide, methyl phenyl sulfone, methyl benzyl sulfone, TBHP, oxygen, diiodo pentoxide, sodium periodate, potassium persulfate, etc.; the organic solvent is one or more of toluene, xylene, trimethylbenzene, benzotrifluoride, ethylbenzene, chlorobenzene, o-dichlorobenzene, anisole, 1, 4-dioxane, dimethyl sulfoxide, N-methyl pyrrolidone and the like; the mol ratio of the 2- (3-indolyl) cyclohexanone compound to the aniline compound to the catalyst to the oxidant is 1: 0.5-5.0: 0.1-1.0: 0.1 to 10; meanwhile, the reaction temperature is 100-200 ℃.
The synthesis method of the invention is that the general formula of the 2- (3-indolyl) cyclohexanone compound is formula II:
Figure 50521DEST_PATH_IMAGE005
Ⅱ
wherein
R1Selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a benzyl group; a substituted or unsubstituted C6-C20 aryl group;
R2selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogen; an alkoxy group; an ester group; a substituted or unsubstituted C6-C20 aryl group;
R3selected from hydrogen atoms; a linear chain of C1-C10.
In the method, the 2- (3-indolyl) cyclohexanone compound in the formula II is selected from 2- (3-indolyl) cyclohexanone; 2- (3- (1-methyl) -indole) cyclohexanone; 2- (3- (1-ethyl) -indole); 2- (3- (1-pentenyl) -indole); 2- (3- (1-isopropyl) -indole); 2- (3- (1-cyclohexyl) -indole); 2- (3- (1-benzyl) -indole); 2- (3- (1, 4 dimethyl) -indole) cyclohexanone; 2- (3- (1, 5 dimethyl) -indole) cyclohexanone; 2- (3- (1, 6 dimethyl) -indole) cyclohexanone; 2- (3- (1, 7 dimethyl) -indole) cyclohexanone; 2- (3- (1-methyl-5 fluoro) -indole) cyclohexanone; 2- (3- (1-methyl-5-bromo) -indole) cyclohexanone; 2- (3- (1-methyl-6-carboxylic acid methyl ester) -indole) cyclohexanone; 2- (3- (1-methyl-6-chloro) -indole) cyclohexanone; 2- (3- (1-methyl) -indole) -2-methylcyclohexanone; 2- (3- (1-methyl) -indole) -4-methylcyclohexanone.
According to the method, the general formula of the aniline compound is shown as a formula III:
Figure 344099DEST_PATH_IMAGE006
Ⅲ
wherein
R4Selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a carboxyl group; an ester group; an alkoxy group; halogen; a trifluoromethyl group; a substituted or unsubstituted C6-C20 aryl group;
according to the synthesis method, the aniline compound is selected from aniline; 2-methylaniline; 2-phenylaniline; 2-chloroaniline; 3-methylaniline; 3-tert-butylaniline; 3-fluoroaniline; 3-chloroaniline; 3-bromoaniline; 3-trifluoromethylaniline; 3-trifluoromethoxyaniline; 3-nitroaniline; 3-carboxylic acid methyl ester aniline; 3-cyanoaniline; 4-methylaniline, 4-phenylaniline; 4-fluoroaniline; 4-chloroaniline; 4-chloroaniline; 4-bromoaniline; 4-methoxyaniline; 4-trifluoromethoxyaniline; 4-nitroaniline; 4-acetanilide; 3, 3-dibromoaniline, 2-naphthylamine; 2-anthracenamine; 5-amino-2, 2-difluoro-1, 3-benzodioxazole; 1, 3-benzothiazol-5-amine.
The indolo [2,3 ] is formed by the formulas I, II and III-b]Indole and derivatives thereof are synthesized into the general formula of the reaction system of the invention, as
Figure 56840DEST_PATH_IMAGE007
The method comprises the following steps:
the preparation method comprises the steps of adding a 2- (3-indolyl) cyclohexanone compound, an aniline compound, an iodine reagent, an oxidant and an organic solvent into a reaction vessel;
heating after fully mixing the reactants;
performing purification after the reaction to obtain a product;
wherein the iodine reagent is one or more of methyl sulfoxide iodide, ammonium iodide, potassium iodide, iodine chloride, iodobenzene, diethyl iodobenzene, N-iodosuccinimide, and diiodo pentoxide, preferably trimethyl sulfoxide iodide; the oxidant is one or more of dimethyl sulfoxide, methyl phenyl sulfone, methyl benzyl sulfone, TBHP, oxygen, diiodo pentaoxide, sodium periodate, potassium persulfate, etc., preferably dimethyl sulfoxide; the organic solvent is a single solvent or a mixed solvent of toluene, xylene, trimethylbenzene, trifluorotoluene, ethylbenzene, chlorobenzene, o-dichlorobenzene, anisole, 1, 4-dioxane, dimethyl sulfoxide, N-methylpyrrolidone and the like, and toluene is preferred; the mol ratio of the 2- (3-indolyl) cyclohexanone compound to the aniline compound to the catalyst to the oxidant is 1: 0.5-5.0: 0.1-1.0: 0.1 to 10, preferably 1: 1.5: 0.2: 5; the temperature T of the reaction is between 100 ℃ and 200 ℃, preferably 140 ℃.
In a word, the compound has the advantages that the reaction raw materials are cheap and easy to obtain, and pretreatment is not needed; the reaction does not need to use a catalyst and a metal oxidant or peroxide; only iodine is used as an accelerant, the reaction is directly synthesized in one pot, and the like; the method solves the problems of high cost and the like caused by the conventional multi-step synthesis method; the reaction condition is mild, and the temperature required by the reaction is greatly lower than the reaction temperature of the previous multi-step synthesis; synthetic series of indolo [2,3 ]-b]The indole compound has quite high potential application value.
Referring to the drawings, examples 1-64 are as follows:
example 15-methyl-6-phenyl-5, 6-indolino [2,3 ]-b]Synthesis of indoles
Figure 512092DEST_PATH_IMAGE009
A reaction tube was charged with 0.04 mmol (8.8 mg) of trimethylsulfoxonium iodide, 0.2 mmol (45.4 mg) of 2- (3- (1-methyl) indole) cyclohexanone, 0.3 mmol (27.3. mu.L) of aniline, 1.0 mmol (71.0. mu.L) of dimethyl sulfoxide and 0.5 mL of toluene, and the mixture was sealed and stirred at 140 ℃ to effect reaction for 16 hours, followed by ordinary treatment to obtain 41.5 mg of a pure product in 70% yield.
Following the procedure of example 1, the present invention synthesized the following compounds:
Figure 693806DEST_PATH_IMAGE010
Figure 525496DEST_PATH_IMAGE011
Figure 92744DEST_PATH_IMAGE012
Figure 718897DEST_PATH_IMAGE013
Figure 637174DEST_PATH_IMAGE014
Figure 272555DEST_PATH_IMAGE015
Figure 428730DEST_PATH_IMAGE016
the following gives the characterization data of the compounds of some examples of the present invention, such as nuclear magnetic spectrum, high resolution mass spectrum, etc.:
the nuclear magnetic and mass spectral data of the product of example 1 are as follows:
1H NMR (400 MHz, CDCl3) δ7.98 (t, J = 6.8 Hz, 2H), 7.67-7.52 (m, 5H), 7.37-7.30 (m, 3H), 7.28 (d, J = 7.8 Hz, 1H), 7.24 (d, J = 7.8 Hz, 1H), 7.17 (d, J = 7.6 Hz, 1H), 3.50 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 145.1, 141.3 140.2, 137.2, 129.9, 128.6, 128.2, 122.4, 121.8, 121.1, 120.3 120.0, 120.0, 118.6, 118.3 110.3 109.3 101.2, 30.8.
the nuclear magnetic and mass spectral data of the product of example 2 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.97 (t, J = 6.8 Hz , 2H), 7.52-7.45 (m, 3H), 7.43 (d, J = 7.4 Hz, 1H), 7.34-7.29 (m, 3H), 7.25-7.22 (m, 1H), 7.14 (t, J = 7.6 Hz, 1H), 6.97 (d, J = 8.2 Hz, 1H), 3.41 (s, 3H), 2.05 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 145.1, 140.8, 140.0, 137.9, 135.8, 131.4, 129.6, 129.5, 127.4, 122.2, 122.0, 120.8, 120.3 119.9, 119.7, 118.5, 118.3 110.3 109.2, 100.6, 29.8, 17.5; HRMS (ESI) m/z: [M+H]+ calcd for C22H19N2 + 311.1543; found 311.1542.
the nuclear magnetic and mass spectral data of the product of example 3 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.91 (d, J = 7.6 Hz, 2H), 7.72 (d, J = 7.4 Hz, 1H), 7.70-7.64 (m, 1H), 7.58 (d, J = 4.4 Hz, 2H), 7.32-7.26 (m, 2H), 7.23-7.18 (m, 2H), 7.16-7.10 (m, 4H), 7.09-7.03 (m, 3H); 13C NMR (100 MHz, CDCl3) δ 145.0, 141.5, 141.4, 140.0, 137.8, 134.3 131.6, 130.5, 129.7, 128.8, 128.5, 128.1, 127.9, 122.2, 121.8, 120.8, 120.0, 119.9, 119.5, 118.4, 118.2, 110.5, 109.0, 100.9, 29.9; HRMS (ESI) m/z: [M+H]+ calcd for C27H21N2 + 373.1699; found 373.1700.
the nuclear magnetic and mass spectral data of the product of example 4 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.91 (t, J = 7.2 Hz, 2H), 7.64 (d, J = 7.6 Hz, 1H), 7.57 (d, J = 6.8 Hz, 1H), 7.52-7.44 (m, 2H), 7.32-7.27 (m, 2H), 7.26-7.20 (m, 2H), 7.10 (t, J = 7.8 Hz, 1H), 6.96 (d, J = 8.0 Hz, 1H), 3.43 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 144.9, 140.8, 139.9, 134.8, 134.4, 131.2, 130.9, 130.6, 128.2, 122.5, 121.8, 121.3 120.3 120.1, 119.9, 118.7, 118.4, 110.2, 109.2, 101.0, 29.8; HRMS (ESI) m/z: [M+H]+ calcd for C21H16ClN2 +331.0997; found 331.0996.
the nuclear magnetic and mass spectral data of the product of example 5 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.95 (t, J = 7.6 Hz, 2H), 7.49 (t, J = 7.6 Hz, 1H), 7.41-7.33 (m, 4H), 7.30 (t, J = 7.4 Hz, 2H), 7.26-7.21 (m, 2H), 7.15 (t, J = 7.6 Hz, 1H), 3.52 (s, 3H), 2.49 (s, 3H); 13C NMR (100 MHz, CDCl3) δ145.2, 141.3 140.2, 140.0, 137.1, 129.6, 129.4, 128.8, 125.2, 122.4, 121.9, 121.0, 120.3 119.9, 119.9, 118.6, 118.3 110.4, 109.2, 101.1, 30.8, 21.5; HRMS (ESI) m/z: [M+H]+ calcd for C22H19N2 + 311.1543; found 311.1542.
the nuclear magnetic and mass spectral data of the product of example 6 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.96 (t, J = 6.8 Hz, 2H), 7.60-7.52 (m, 3H), 7.44-7.39 (m, 1H), 7.37-7.29 (m, 3H), 7.27-7.23 (m, 2H), 7.16 (t, J = 7.2 Hz, 1H), 3.52 (s, 3H), 1.40 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 153.4, 145.1, 141.2, 140.3 136.9, 129.4, 125.4, 125.3 125.1, 122.3 121.9, 121.0, 120.3 120.0, 119.9, 118.6, 118.3 110.4, 109.2, 101.2, 35.1, 31.4, 30.8; HRMS (ESI) m/z: [M+H]+ calcd for C25H25N2 + 353.2012; found 353.2012.
the nuclear magnetic and mass spectral data of the product of example 7 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.96 (t, J = 7.8 Hz, 2H), 7.58 (q, J = 7.4 Hz 1H), 7.39-7.30 (m, 5H), 7.29 (s, 1H), 7.26 (d, J = 8.4 Hz, 2H), 7.18 (t, J= 7.6 Hz, 1H), 3.54 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 163.2 (d, J = 249.7 Hz), 144.7, 141.0, 140.3, 138.8 (d, J = 9.7 Hz), 131.1 (d, J = 9.2 Hz), 123.9 (d, J = 3.3 Hz), 122.6, 121.8, 121.5, 120.5, 120.3, 120.2 118.7, 118.4 115.8, 115.6 (d, J = 4.0 Hz), 115.4, 109.8 (d, J = 81.0 Hz), 101.7, 31.0; 19F NMR (376 MHz, CDCl3) δ-110.1; HRMS (ESI) m/z: [M+H]+ calcd for C21H16FN2 + 315.1292; found 315.1292.
the nuclear magnetic and mass spectral data of the product of example 8 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.95 (t, J = 8.2 Hz, 2H), 7.60 (s, 1H), 7.57-7.50 (m, 2H), 7.50-7.44 (m, 1H), 7.37-7.29 (m, 3H), 7.28-7.22 (m, 2H), 7.17 (t, J = 7.6, Hz, 1H), 3.53 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 144.7, 141.0, 140.2, 138.5, 135.5, 130.8, 128.8, 128.3 126.3 122.6, 121.7, 121.5, 120.5, 120.3 120.2, 118.7, 118.4, 110.2, 109.4, 101.7, 31.1; HRMS (ESI) m/z: [M+H]+ calcd for C21H16ClN2 + 331.0997; found 311.0996.
the nuclear magnetic and mass spectral data of the product of example 9 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.96 (t, J = 8.2 Hz, 2H), 7.76 (s, 1H), 7.68 (d, J = 7.6 Hz, 1H), 7.53-7.46 (m, 2H), 7.36 (d, J = 3.6 Hz, 1H), 7.34-7.28 (m, 2H), 7.25 (t, J = 8.0 Hz, 2H), 7.18 (t, J = 7.6 Hz, 1H), 3.53 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 144.7, 141.0, 140.2, 138.6, 131.6, 131.1, 131.1, 126.7, 123.2, 122.6, 121.7, 121.5, 120.4, 120.3 120.2, 118.7, 118.4, 110.2, 109.4, 101.7, 31.0; HRMS (ESI) m/z: [M+H]+ calcd for C21H16BrN2 + 375.0491; found 375.0492.
the nuclear magnetic and mass spectral data of the product of example 10 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.97 (t, J = 7.0 Hz, 2H), 7.87 (s, 1H), 7.82 (d, J = 7.2 Hz, 1H), 7.78-7.73 (m, 2H), 7.39-7.27 (m, 4H), 7.24-7.16 (m, 2H), 3.50 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 144.4, 140.8, 140.1, 137.9, 132.4 (q, J = 33.2 Hz), 131.1, 130.4, 125.0 (q, J = 3.7 Hz), 124.7 (q, J = 3.7 Hz), 123.1(q, J = 270.9 Hz), 122.6, 121.5, 120.4, 120.2, 120.2, 118.6, 118.4, 109.9, 109.3, 101.8 30.9; 19F NMR (376 MHz, CDCl3) δ-62.6; HRMS (ESI) m/z: [M+H]+ calcd for C22H16F3N2 + 365.1260; found 365.1261.
the nuclear magnetic and mass spectral data of the product of example 11 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.96 (t, J = 7.6 Hz, 2H), 7.65 (t, J = 8.0 Hz, 1H), 7.54 (d, J = 8.6 Hz, 1H), 7.48 (s, 1H), 7.41 (d, J = 8.2 Hz, 1H), 7.39-7.33 (m, 2H), 7.33-7.31 (m, 1H), 7.30 (d, J = 4.6 Hz, 1H), 7.26 (t, J =6.8 Hz, 1H), 7.18 (t, J =7.2 Hz, 1H), 3.54 (s, 3H); 13C NMR (100 MHz, CDCl3) δ150.0, 144.6, 140.9, 140.3 138.8, 131.1, 126.3 122.7, 121.7, 121.6, 120.9, 120.7, 120.6 (q, J = 256.7)120.5, 120.4, 120.4, 118.7, 118.5, 110.1, 109.4, 101.9, 31.0; 19F NMR (376 MHz, CDCl3) δ-57.8; HRMS (ESI) m/z: [M+H]+ calcd for C22H16F3N2O+ 381.1209; found 381.1208.
the nuclear magnetic and mass spectral data of the product of example 12 are as follows:
1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 1H), 8.43 (d, J = 8.2 Hz, 1H), 8.20 (d, J = 9.8 Hz, 1H), 7.96 (t, J = 8.2 Hz, 3H), 7.54 (d, J = 9.0 Hz, 1H), 7.32-7.18 (m, 4H), 7.13 (t, J = 7.2 Hz, 1H), 3.54 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 148.7, 144.2, 140.3 139.8, 137.3 134.4, 131.4, 123.3 122.6, 122.0, 121.4, 120.7, 120.3 120.1, 120.1, 118.2, 118.1, 110.0, 100.7, 31.0; HRMS (ESI) m/z: [M+H]+ calcd for C22H16N3O2 + 342.1237; found 342.1236.
the nuclear magnetic and mass spectral data of the product of example 13 are as follows:
1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 8.22 (d, J = 7.8 Hz, 1H), 7.95 (t, J = 7.2 Hz, 2H), 7.78 (d, J = 8.0 Hz, 1H), 7.70 (t, J = 7.8 Hz, 1H), 7.37-7.28 (m, 3H), 7.24 (d, J = 8.0 Hz, 1H), 7.20 (d, J = 7.9 Hz, 1H), 7.15 (t, J = 7.2 Hz, 1H), 3.97 (s, 3H), 3.51 (s, 3H); 13C NMR (100 MHz, CDCl3) δ166.1, 144.8, 141.1, 140.2, 137.6, 132.3 132.1, 130.0, 129.5, 129.0, 122.6, 121.7, 121.4, 120.4, 120.2, 120.2, 118.7, 118.4, 110.1, 109.3 101.7, 52.6, 31.0; HRMS (ESI) m/z: [M+H]+ calcd for C23H19N2O2 + 355.1441; found 355.1441.
the nuclear magnetic and mass spectral data of the product of example 14 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.93 (t, J = 7.0, 2H), 7.89 (s, 1H), 7.82 (d, J = 8.4 Hz, 2H), 7.78-7.72 (m, 1H), 7.39-7.32 (m, 2H), 7.30 (d, J = 8.2 Hz, 2H), 7.20-7.12 (m, 2H), 3.52 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 144.4, 140.9, 140.2, 138.5, 132.4, 131.9, 131.2, 131.0, 122.8, 121.9, 121.6, 120.7, 120.6, 118.8, 118.6, 117.7, 114.3 109.9, 109.5, 102.2, 31.2; HRMS (ESI) m/z: [M+H]+ calcd for C22H16N3 + 322.1339; found 322.1339.
the nuclear magnetic and mass spectral data of the product of example 15 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.95 (t, J = 7.2 Hz, 2H), 7.47-7.38 (m, 4H), 7.36-7.28 (m, 3H), 7.26-7.18 (m, 2H), 7.14 (t, J = 7.2 Hz, 1H), 3.51 (s, 3H), 2.52 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 145.2, 141.4, 140.2, 138.7, 134.4, 130.5, 128.1, 122.3 121.9, 120.9, 120.2, 119.9, 119.8, 118.5, 118.2, 110.3 109.2, 101.0, 30.7, 21.4; HRMS (ESI) m/z: [M+H]+ calcd for C22H19N2 + 311.1543; found 311.1543.
the nuclear magnetic and mass spectral data of the product of example 16 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.94 (t, J = 6.8, 2H), 7.76 (d, J = 8.2 Hz, 2H), 7.67 (d, J = 7.4 Hz, 2H), 7.56 (d, J = 8.2 Hz, 2H), 7.49 (t, J = 7.6 Hz, 2H), 7.41 (t, J = 7.4 Hz, 1H), 7.34-7.27 (m, 3H), 7.25-7.20 (m, 2H), 7.13 (t, J = 8.2 Hz, 1H), 3.50 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 145.0, 141.4, 141.3 140.2, 140.0, 136.2, 129.1, 128.4, 128.4, 128.0, 127.3 122.5, 121.9, 121.1, 120.3 120.1, 120.0, 118.6, 118.3 110.4, 109.3 101.4, 30.9; HRMS (ESI) m/z: [M+H]+ calcd for C27H21N2 + 373.1699; found 373.1798.
the nuclear magnetic and mass spectral data of the product of example 17 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.91 (t, J = 7.0 Hz, 2H), 7.51-7.45 (m, 2H), 7.31-7.27 (m, 3H), 7.26-7.21 (m, 3H), 7.14-7.08 (m, 2H), 3.44 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 162.4 (d, J = 249.0 Hz), 145.0, 141.4, 140.1, 133.6 (d, J = 3.2 Hz), 130.1 (d, J = 8.7 Hz), 122.4, 121.8, 121.2, 120.4, 120.1, 120.07, 118.6, 118.4, 116.9 (d, J = 22.8 Hz), 110.1 109.1, 101.2, 30.7; 19F NMR (376 MHz, CDCl3) δ-112.1; HRMS (ESI) m/z: [M+H]+ calcd for C21H16FN2 + 315.1292; found 315.1268.
the nuclear magnetic and mass spectral data of the product of example 18 are as follows:
1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, J = 7.2 Hz, 2H), 7.74 (s, 4H), 7.52 (d, J = 6.6 Hz, 1H), 7.28-7.17 (m, 3H), 7.12 (m, 2H), 3.53 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 144.3 140.4, 139.7, 135.2, 133.1, 130.0, 129.8, 121.7, 121.0, 120.8, 120.1, 120.0, 119.9, 118.1, 118.0, 110.0, 109.9, 100.3 30.7; HRMS (ESI) m/z: [M+H]+ calcd for C21H16ClN2 + 331.0997; found 311.0959.
the nuclear magnetic and mass spectral data of the product of example 19 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.92 (t, J = 7.4 Hz, 2H), 7.47 (d, J = 8.8 Hz, 2H), 7.36-7.26 (m, 3H), 7.25-7.19 (m, 1H), 7.15-7.08 (m, 4H), 3.93 (s, 3H), 3.50 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 159.8, 145.4, 141.7, 140.2, 129.7, 122.2, 121.9, 120.9, 120.3 119.9, 119.8, 118.5, 118.2, 115.0, 110.3 109.2, 100.8, 55.8, 30.6; HRMS (ESI) m/z: [M+H]+ calcd for C22H19N2O+ 327.1492; found 327.1487.
the nuclear magnetic and mass spectral data of the product of example 20 are as follows:
1H NMR (400 MHz, CDCl3) δ 7.91 (t, J = 7.2 Hz, 2H), 7.53 (d, J = 8.8 Hz, 2H), 7.40 (d, J = 8.6 Hz, 2H), 7.31-7.28 (m, 2H), 7.27-7.20 (m, 2H), 7.13 (d, J = 6.8 Hz, 2H), 3.44 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 148.9, 144.8, 141.2, 140.2, 135.7, 129.6, 122.5, 122.3 121.7, 121.4, 120.9 (q, J = 256.6)120.3 120.2, 118.7, 118.4, 110.1, 109.4, 101.6, 30.9. 19F NMR (376 MHz, CDCl3) δ-57.8; HRMS (ESI) m/z: [M+H]+ calcd for C22H16F3N2O+ 381.1209; found 381.1172.
it should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (10)

1. Indolo [2,3 ]-b]Indoles and derivatives thereof having the general formula:
Figure 459164DEST_PATH_IMAGE001
Ⅰ
wherein
R1Selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a benzyl group; a substituted or unsubstituted C6-C20 aryl group;
R2selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogen; an alkoxy group; an ester group;
R3selected from hydrogen atoms; a linear chain of C1-C10;
R4selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogen; an alkoxy group; an ester group; a nitro group; a cyano group; a trifluoromethyl group; a trifluoromethoxy group; acetyl; substituted or unsubstituted C6-C14 aryl.
2. A process for the synthesis of indolo [2,3 ] as described in claim 1-b]The indole preparation method is characterized in that a catalyst, an oxidant, an aniline compound, 2- (3-indolyl) cyclohexanone and derivatives thereof and an organic solvent are mixed and then heated for reaction, and finally the product is obtained after purification.
3. The method of claim 2, wherein the catalyst is an iodine reagent selected from the group consisting of: one or more of trimethyl sulfoxide iodide, ammonium iodide, potassium iodide, elementary iodine, iodine chloride, iodobenzene, diethyl iodobenzene, N-iodosuccinimide and diiodo pentoxide.
4. The method of claim 2, wherein the oxidizing agent is selected from the group consisting of: one or more of dimethyl sulfoxide, methyl phenyl sulfone, methyl benzyl sulfone, TBHP, oxygen, diiodo pentoxide, sodium periodate, potassium persulfate, etc.
5. The synthesis method according to claim 2, wherein the organic solvent is one or more selected from toluene, xylene, trimethylbenzene, trifluorotoluene, ethylbenzene, chlorobenzene, o-dichlorobenzene, anisole, 1, 4-dioxane, dimethyl sulfoxide, and N-methylpyrrolidone.
6. The method of claim 2, wherein the molar ratio of the 2- (3-indolyl) cyclohexanone compound to the aniline compound to the catalyst to the oxidant is 1: 0.5-5.0: 0.1-1.0: 0.1 to 10; meanwhile, the reaction temperature is 100-200 ℃.
7. A synthesis process according to any one of claims 2 to 6, wherein the 2- (3-indolyl) cyclohexanone compound has the formula II:
Figure 659201DEST_PATH_IMAGE002
Ⅱ
wherein
R1Selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a benzyl group; a substituted or unsubstituted C6-C20 aryl group;
R2selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; halogenA peptide; an alkoxy group; an ester group; a substituted or unsubstituted C6-C20 aryl group;
R3selected from hydrogen atoms; a linear chain of C1-C10.
8. The process of claims 2-7, wherein the 2- (3-indolyl) cyclohexanone compound of formula ii is selected from 2- (3-indolyl) cyclohexanone; 2- (3- (1-methyl) -indole) cyclohexanone; 2- (3- (1-ethyl) -indole); 2- (3- (1-pentenyl) -indole); 2- (3- (1-isopropyl) -indole); 2- (3- (1-cyclohexyl) -indole); 2- (3- (1-benzyl) -indole); 2- (3- (1, 4 dimethyl) -indole) cyclohexanone; 2- (3- (1, 5 dimethyl) -indole) cyclohexanone; 2- (3- (1, 6 dimethyl) -indole) cyclohexanone; 2- (3- (1, 7 dimethyl) -indole) cyclohexanone; 2- (3- (1-methyl-5 fluoro) -indole) cyclohexanone; 2- (3- (1-methyl-5-bromo) -indole) cyclohexanone; 2- (3- (1-methyl-6-carboxylic acid methyl ester) -indole) cyclohexanone; 2- (3- (1-methyl-6-chloro) -indole) cyclohexanone; 2- (3- (1-methyl) -indole) -2-methylcyclohexanone; 2- (3- (1-methyl) -indole) -4-methylcyclohexanone.
9. A synthesis process according to any one of claims 2 to 8, characterized in that the aniline compound has the general formula III:
Figure 386986DEST_PATH_IMAGE003
Ⅲ
wherein
R4Selected from hydrogen atoms; a linear, branched alkyl group of C1-C10; a carboxyl group; an ester group; an alkoxy group; halogen; a trifluoromethyl group; substituted or unsubstituted C6-C20 aryl.
10. The method of claims 2-8, the aniline compound is selected from aniline; 2-methylaniline; 2-phenylaniline; 2-chloroaniline; 3-methylaniline; 3-tert-butylaniline; 3-fluoroaniline; 3-chloroaniline; 3-bromoaniline; 3-trifluoromethylaniline; 3-trifluoromethoxyaniline; 3-nitroaniline; 3-carboxylic acid methyl ester aniline; 3-cyanoaniline; 4-methylaniline, 4-phenylaniline; 4-fluoroaniline; 4-chloroaniline; 4-chloroaniline; 4-bromoaniline; 4-methoxyaniline; 4-trifluoromethoxyaniline; 4-nitroaniline; 4-acetanilide; 3, 3-dibromoaniline, 2-naphthylamine; 2-anthracenamine; 5-amino-2, 2-difluoro-1, 3-benzodioxazole; 1, 3-benzothiazol-5-amine.
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