CN104496881A - Preparation method for synthesizing indoline from amide compounds by catalysis of copper salt - Google Patents

Preparation method for synthesizing indoline from amide compounds by catalysis of copper salt Download PDF

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CN104496881A
CN104496881A CN201410820260.3A CN201410820260A CN104496881A CN 104496881 A CN104496881 A CN 104496881A CN 201410820260 A CN201410820260 A CN 201410820260A CN 104496881 A CN104496881 A CN 104496881A
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indoline
drip
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CN104496881B (en
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邱仁华
李宁波
许新华
龙进国
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Hunan University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

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Abstract

The invention provides a catalytic synthesis method for the catalytic synthesis of indoline. The method comprises the following steps of adding a suitable ligand into easily prepared amide compounds serving as raw materials, and in the presence of a copper salt as a catalyst and peroxide as an oxidant, in a polar solvent, carrying out reflux reaction to obtain the corresponding indoline compound at 80-160 DEG C. In the reaction, the copper salt is used as the catalyst, the cost is low, the toxicity is very small, the environment-friendly concept is achieved, the catalyst can have better catalytic effect on a complex substrate and the diversity of products is extremely enriched. The catalytic synthesis method has the main advantages of simple experiment, high yield, wide applicability and stronger practicality; the reaction is performed in the absence of alkali and the efficient, economical and low-toxicity vision is achieved in a real sense.

Description

A kind of preparation method of mantoquita catalysis amides synthesizing indoline
[technical field]
The invention belongs to transition metal-catalyzed organic synthesis field, relate in particular to mantoquita as catalyzer, catalyzer is made with mantoquita that is cheap, low toxicity, with amide compound compounds for raw material, take superoxide as oxygenant, add part, in organic solvent autoimmunity syndrome ring closure reaction occurs, high productivity obtains the process for catalytic synthesis of indoline-like derivative.
[background technology]
The advantages such as copper catalytic coupling is efficient with it, economy, low toxicity are drawn and are enjoyed people to pay close attention to.Particularly nearly ten years, due to the improvement (particularly the exploitation of all kinds of efficient ligand) of various catalytic condition, copper catalyzed coupling reaction is obtained and develops rapidly.Along with going deep into of copper catalyticing research, the cascade reaction utilizing copper catalytic coupling to participate in builds all kinds of heterocycle, becomes an important directions of chemist research mantoquita.Wherein copper catalysis prepare organic compounds containing nitrogen be organic chemistry research in study hotspot and difficult point.
Because nitrogen-containing heterocycle compound has important biomolecule bioactive molecule, be the important composition unit of some medicines, wherein benzo nitrogen-containing hetero compound is mostly containing biological activity, is prevalent in the middle of medicine.Therefore, the research for nitrogen-containing benzoheterocycle compounds gets most of the attention especially, particularly indoline-like derivative.The method of conventional synthesis indoline-like derivative is generally that this method needs hydrogenating reduction, borohydride reduction, metal-acid reduction etc. by being reduced into corresponding indoline derivative thing having substituent indole derivatives.But the method for hydrogenating reduction requires High Temperature High Pressure, require high to reaction unit, easily produce by product; The reduction method of hydroborate, reductive agent price is more expensive, and cost is higher, is difficult to realize industrial production; Metal-sour reduction system can produce a large amount of waste acid waters, has also used mercury, has larger toxicity, can produce pollution to environment.Thus, continue to be badly in need of exploitation convenient, synthetic method efficiently.
In recent years, along with deepening continuously of the hydrocarbon Study of Activation of transition metal, this research theory is applied to the deficiency that can make up reduction method to the synthesis of indoline derivative thing, and can realize convenient, efficient, economic vision.Based on this, we devise with amide compound is raw material, and under mantoquita catalysis, synthesized a series of indoline derivative thing, this method is without the need to specific installation, and productive rate is higher, and environmentally friendly.
[summary of the invention]
The object of the present invention is to provide a kind of green catalysis synthetic method of indoline derivative thing.Mantoquita makes catalyzer, amides II reaction raw materials, and superoxide is oxygenant, adds suitable part, obtains sulfonylindoline compounds I.Due to this catalyst system, to have cost lower, and catalytic activity is high, simple to operate, and toxicity is little, and easily the advantage such as process, has certain feasibility for industrialized realization.
To achieve the above object of the invention, the present invention proposes following technical scheme:
In above-mentioned synthetic method, described amides II and sulfonylindoline compounds I, I and II is as follows for its structural formula:
Wherein, R 1for one on phenyl ring 3,4,5,6 replace or two replacement H, Br, Cl, I, SO 3h, C (CH 3) 3, CH 3, OCH 3, Py, Ph, Cy, 4-H 3cOC 6h 4, C 6h 5one in S, wherein disubstituted group can identical also can be different; When X is C, R 2for H, CH 3, CH 2cH 2cH 3, CH 2cH 2cl, OCH 3, OC (CH 3) 3, C (CH 3) 3, Bn, Py, Cy, Ph, C 4h 4s, CH 2cHPh, 2,6-di-F-C 6h 3, 2-F 3c-C 6h 4, 2-H 3c-C 6h 4, 2,6-di-CH 3-C 6h 3, 2,6-diCH 3o-C 6h 3, CHCH 2, 2-CH 3o-C 6h 4, C 6h 5, CHCHCH 3one; When X is S=O, R 2for 4-O 2nC 6h 4, 4-H 3cOC 6h 4one; R 3and R 4can be identical or different CH 3, CH 2oAc, CH 2oCH 3, CH 2sPh, CHCHCH 3, Ph, Cy, CH 2cH 3, one in Bn;
In above-mentioned synthetic method, catalyzer is that mantoquitaization is cuprous, cuprous bromide, cupric chloride, the one of cuprous chloride; The consumption of described catalyzer is 0.1-3 equivalent (be 1 equivalent with amide compound compounds, lower with); Described organic solvent is the one of DMSO, DMF, acetonitrile, toluene, parachlorotoluene, sym-trimethylbenzene; Described part is nitrogen Methylimidazole, PA, 2-minaline, benzo three nitrogen, 4-methylimidazole, triphenylphosphine, the one in pyridine, and wherein mole addition of part is 1-3 equivalent; Described oxygenant is hydrogen peroxide, t-butyl hydroperoxide, di-t-butyl peroxide, the one of tert-butyl peroxide isopropyl (base) benzene, and mole addition of oxygenant is 0.1-10 equivalent; The condition of described catalyzed reaction is: at 80-160 DEG C, react 4-40 hour.
The efficient catalytic synthetic method of a kind of synthesis of indole quinoline derivant provided by the present invention, open new economy " green " approach, its advantage is: the amides as raw material is more, the selectivity of target product and productive rate are all higher, experimental implementation is simple, catalytic activity is high simultaneously, and toxicity is little, easily processes.
[accompanying drawing explanation]
It is the path profile of synthesizing indoline compound provided by the invention shown in Fig. 1.
[embodiment]
Mantoquita provided by the present invention catalyzes and synthesizes the synthetic route of indoline, refers to accompanying drawing 1: add in reaction vessel by raw material acid amides, part, oxygenant and catalyzer, add solvent, do not need N 2protection, reacts 4-40h, obtains target compound through column chromatography for separation under the environment of 80-160 DEG C.
Below in conjunction with concrete preparation example, the present invention will be further described: below in conjunction with concrete preparation example, the present invention will be further described:
preparation example 1
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=H, R 3, R 4=CH 3), add cuprous bromide (0.25eq), nitrogen Methylimidazole (3eq), drip di-t-butyl peroxide (1eq), drip DMF 2mL, react and carry out 24h at 100 DEG C.After reaction terminates, obtain 3,3-dimethyl indole quinoline-1-formaldehyde through column chromatography for separation, productive rate is 91%.
preparation example 2
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=CH 3, R 3=CH 2oAc, R 4=CH 3), add cuprous chloride (1eq), nitrogen Methylimidazole (2eq), drip hydrogen peroxide (3eq), drip acetonitrile 2mL, react and carry out 12h at 140 DEG C.After reaction terminates, obtain 3-methyl-3-methyl acetate base indoline-1-ethyl ketone through column chromatography for separation, productive rate is 93%.
preparation example 3
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=CH 3, R 3, R 4=Cy), add cuprous chloride (0.25eq), PA (1eq), drip hydrogen peroxide (2eq), drip parachlorotoluene 2mL, react and carry out 24h at 130 DEG C.After reaction terminates, obtain 3,3-dicyclohexyl indoline-1-ethyl ketone through column chromatography for separation, productive rate is 89%.
preparation example 4
Amides II (X=S=O, R is added in 10mL reaction tubes 1=H, R 2=4-O 2nC 6h 4, R 3=CH 2sPh, R 4=CH 3), add cuprous bromide (3eq), PA (3eq), drip hydrogen peroxide (3eq), drip DMF 2mL, react and carry out 24h at 100 DEG C.After reaction terminates, obtain 3-methyl-3-benzene sulphur methyl ether base-1-4 '-nitrobenzenesulfonyl indoline through column chromatography for separation, productive rate is 91%.
preparation example 5
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=Bn, R 3=Br, R 4=CH 2cH 3), add cuprous iodide (0.1eq), nitrogen Methylimidazole (2eq), drip t-butyl hydroperoxide (1eq), drip acetonitrile 2mL, react and carry out 12h at 140 DEG C.After reaction terminates, obtain 3-ethyl-3 bromo indole quinoline-1-benzyl ketone through column chromatography for separation, productive rate is 87%.
preparation example 6
Amides II (X=C, R is added in 10mL reaction tubes 1=6-4 '-C 6h 5oCH 3, R 2=CH (CH 3) 2, R 3=Ph, R 4=CH 2oAc), add cuprous bromide (1.5eq), PA (3eq), drip tert-butyl peroxide isopropyl (base) benzene (1eq), drip parachlorotoluene 2mL, react and carry out 24h at 130 DEG C.After reaction terminates, obtain 7-4 '-p-methoxy-phenyl 4-methyl acetate base-3-Phenylindole quinoline-1-isopropyl-ketone through column chromatography for separation, productive rate is 89%.
preparation example 7
Amides II (X=C, R is added in 10mL reaction tubes 1=6-C 6h 6, R 2=CH 2cH 3, R 3=CH 2oCH 3, R 4=Cy), add cuprous bromide (2eq), 2-minaline (2eq), drip hydrogen peroxide (2eq), drip DMF 2mL, react and carry out 24h at 100 DEG C.After reaction terminates, obtain 3-ether base-4 cyclohexyl-7-Phenylindole quinoline-1-acetone through column chromatography for separation, productive rate is 83%.
preparation example 8
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2,6-di-F-C 6h 3, R 3=Ph, R 4=CH 2sPh), add cuprous bromide (1.5eq), pyridine (3eq), drip t-butyl hydroperoxide (1eq), drip DMSO 2mL, react and carry out 12h at 160 DEG C.After reaction terminates, obtain 3-phenyl-3-methyl-phenoxide base indoline-1-2 ' through column chromatography for separation, 6 '-difluorophenyl ketone, productive rate is 92%.
preparation example 9
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2-O 2n-C 6h 4, R 3, R 4=CH 2oAc), add cuprous chloride (2eq), nitrogen Methylimidazole (2eq), drip di-t-butyl peroxide (3eq), drip DMF2mL, react and carry out 40h at 100 DEG C.After reaction terminates, obtain 3,3-oxalic acid methoxycarbonyl indoline-1-2 '-nitrophenyl ketone through column chromatography for separation, productive rate is 84%.
preparation example 10
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=4-F-C 6h 4, R 3=CH 2cH 3, R 4=Cy), add cuprous chloride (0.25eq), 2-minaline (3eq), drip di-t-butyl peroxide (1eq), drip DMSO 2mL, react and carry out 12h at 160 DEG C.After reaction terminates, obtain 3-ethyl-3 cyclohexyl indole quinoline-1-4 '-fluorophenyl ketone through column chromatography for separation, productive rate is 67%.
preparation example 11
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=C 6h 5, R 3=Bn, R 4=CH 3), add cuprous iodide (3eq), benzo three nitrogen (2eq), drip hydrogen peroxide (2eq), drip parachlorotoluene 2mL, react and carry out 24h at 130 DEG C.After reaction terminates, obtain 3-methyl-3-benzylindole quinoline-1-phenyl ketone through column chromatography for separation, productive rate is 92%.
preparation example 12
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2-CH 3-c 6h 4, R 3, R 4=CH 2sPh), add cuprous bromide (2eq), PA (3eq), drip tert-butyl peroxide isopropyl (base) benzene (3eq), drip equal toluene(mono)chloride 2mL, react and carry out 4h at 160 DEG C.After reaction terminates, obtain 3,3-bis-thioanisole base indoline-1-2 '-aminomethyl phenyl ketone through column chromatography for separation, productive rate is 94%.
preparation example 13
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2-F-C 6h 4, R 3=CH 2oCH 3, R 4=CH 2oAc), add cuprous bromide (1.5eq), triphenylphosphine (1eq), drip t-butyl hydroperoxide (2eq), drip parachlorotoluene 2mL, react and carry out 24h at 130 DEG C.After reaction terminates, obtain 3-ether base-3 ethyl acetate base indoline-1-2 '-fluorophenyl ketone through column chromatography for separation, productive rate is 82%.
preparation example 14
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2,6-di-H 3cO-C 6h 3, R 3=Ph, R 4=Cy), add cuprous iodide (0.25eq), nitrogen Methylimidazole (2eq), drip di-t-butyl peroxide (1eq), drip DMSO 2mL, react and carry out 12h at 160 DEG C.After reaction terminates, obtain 3-cyclohexyl-3-Phenylindole quinoline-1-2 ' through column chromatography for separation, 6 '-Dimethoxyphenyl ketone, productive rate is 72%.
preparation example 15
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2,4-di-H 3c-C 6h 4, R 3=CH 2sPh, R 4=Cy), add cuprous bromide (1.5eq), 4-methylimidazole (2eq), drip di-t-butyl peroxide (3eq), drip parachlorotoluene 2mL, react and carry out 24h at 130 DEG C.After reaction terminates, obtain 3-cyclohexyl-3-thioanisole base indoline-1-2 ' through column chromatography for separation, 4 '-3,5-dimethylphenyl ketone, productive rate is 74%.
preparation example 16
Amides II (X=C, R is added in 10mL reaction tubes 1=4-SO 3h,R 2=CH 3, R 3=CH 2cH 3, R 4=CH 2oAc), add cuprous bromide (0.25eq), triphenylphosphine (3eq), drip hydrogen peroxide (1eq), drip DMF 2mL, react and carry out 40h at 100 DEG C.After reaction terminates, obtain 3-ethyl-3-methyl acetate base-5-sulfonic group indoline-1-ethyl ketone through column chromatography for separation, productive rate is 23%.
preparation example 17
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2-Py, R 3=CH 2oCH 3, R 4=CH 2sPh), add cuprous chloride (2eq), 4-methylimidazole (2eq), drip t-butyl hydroperoxide (2eq), drip DMF 2mL, react and carry out 24h at 100 DEG C.After reaction terminates, obtain 3-ether base-3-thioanisole base indoline-1-2 '-pyridyl ketone through column chromatography for separation, productive rate is 75%.
preparation example 18
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2-C 4h 4s,R 3, R 4=Cy), add cuprous bromide (3eq), PA (2eq), drip tert-butyl peroxide isopropyl (base) benzene (1eq), drip equal toluene(mono)chloride 2mL, react and carry out 4h at 160 DEG C.After reaction terminates, obtain 3,3-dicyclohexyl indoline-1-2 '-thienyl ketone through column chromatography for separation, productive rate is 85%.
preparation example 19
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=2-F 3c-C 6h 4, R 3=Ph, R 4=CH 2oAc), add cuprous chloride (1eq), 2-minaline (2eq), drip hydrogen peroxide (0.1eq), drip parachlorotoluene 2mL, react and carry out 24h at 130 DEG C.After reaction terminates, obtain 3-methyl acetate base-3-Phenylindole quinoline-1-2 '-trifluoromethyl ketone through column chromatography for separation, productive rate is 77%.
preparation example 20
Amides II (X=C, R is added in 10mL reaction tubes 1=6-CH 3, R 2=C 6h 5, R 3=CH 2cH 3, R 4=CH 2sPh), add cuprous iodide (2eq), PA (2eq), drip di-t-butyl peroxide (2eq), drip DMF 2mL, react and carry out 24h at 100 DEG C.After reaction terminates, obtain 7-methyl-3-ethyl-3-thioanisole base indoline-1-phenyl ketone through column chromatography for separation, productive rate is 95%.
preparation example 21
Amides II (X=C, R is added in 10mL reaction tubes 1=6-Cl, R 2=C 6h 5, R 3=Bn, R 4=Cy), add cuprous chloride (2eq), nitrogen Methylimidazole (1eq), drip di-t-butyl peroxide (2eq), drip DMF 2mL, react and carry out 12h at 100 DEG C.After reaction terminates, obtain 3-cyclohexyl-3-benzyl-7-chloro-indole quinoline-1-phenyl ketone through column chromatography for separation, productive rate is 80%.
preparation example 22
Amides II (X=C, R is added in 10mL reaction tubes 1=4-Py, R 2=Bn, R 3, R 4=CH 2sPh), add cuprous bromide (1.5eq), nitrogen Methylimidazole (2eq), drip di-t-butyl peroxide (2eq), drip parachlorotoluene 2mL, react and carry out 130h at 130 DEG C.After reaction terminates, obtain 3,3-bis-thioanisole base-5-pyridyl indoline-1-benzyl ketone through column chromatography for separation, productive rate is 61%.
preparation example 23
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=CHCHCH 3, R 3=CH 2oCH 3, R 4=CH 2sPh), add cuprous bromide (1eq), PA (1eq), drip hydrogen peroxide (1eq), drip DMF 2mL, react and carry out 24h at 100 DEG C.After reaction terminates, obtain 3-ether base-3-thioanisole base indoline-1-propyl ketone through column chromatography for separation, productive rate is 78%.
preparation example 24
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=C (CH 3) 3, R 3=Ph, R 4=CH 2sPh), add cuprous bromide simple substance (0.25eq), nitrogen Methylimidazole (2eq), drip hydrogen peroxide (10eq), drip DMF 2mL, react and carry out 24h at 100 DEG C.After reaction terminates, obtain 3-phenyl-3-thioanisole base indoline-1-tertiary butyl ketone through column chromatography for separation, productive rate is 85%.
preparation example 25
Amides II (X=C, R is added in 10mL reaction tubes 1=6-Cy, R 2=C 6h 5, R 3=Bn, R 4=CH 2oAc), cuprous bromide simple substance (2eq), 2-minaline (1eq), drips hydrogen peroxide (10eq), drips DMF 2mL, reacts and carry out 24h at 100 DEG C.After reaction terminates, obtain 3-methyl acetate base-7-cyclohexyl-3-benzylindole quinoline-1-phenyl ketone through column chromatography for separation, productive rate is 81%.
preparation example 26
Amides II (X=C, R is added in 10mL reaction tubes 1=6-Cy, R 2=C 6h 5, R 3=Ph, R 4=Cy), cuprous bromide simple substance (1eq), PA (1eq), drips hydrogen peroxide (2eq), drips DMF 2mL, reacts and carry out 24h at 100 DEG C.After reaction terminates, obtain 3,7-dicyclohexyl-3-Phenylindole quinoline-1-phenyl ketone through column chromatography for separation, productive rate is 89%.
preparation example 27
Amides II (X=C, R is added in 10mL reaction tubes 1=H, R 2=CH 2cH 2cl, R 3=CH 2cH 3, R 4=CH 2sPh), cuprous bromide simple substance (0.25eq), 2-minaline (1eq), drips hydrogen peroxide (0.1eq), drips DMF 2mL, reacts and carry out 24h at 100 DEG C.After reaction terminates, obtain 3-ethyl-3-thioanisole base indoline-1-2 '-chloroethyl ketone through column chromatography for separation, productive rate is 84%.
preparation example 28
Amides II (X=C, R is added in 10mL reaction tubes 1=4-Br, R 2=CH 2cH 3, R 3, R 4=Cy), cuprous bromide simple substance (1eq), nitrogen Methylimidazole (1eq), drips hydrogen peroxide (1eq), drips DMF 2mL, reacts and carry out 24h at 100 DEG C.After reaction terminates, obtain 3,3-dimethyl-5-bromo indole quinoline-1-ethyl ketone through column chromatography for separation, productive rate is 92%.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.

Claims (3)

1. the preparation method of a mantoquita catalysis amides autoimmunity syndrome ring closure reaction synthesizing indoline, it is characterized in that, catalyzer is made with mantoquita that is cheap, low toxicity, with amide compound compounds II for raw material, be oxygenant with superoxide, add part, in organic solvent autoimmunity syndrome ring closure reaction occurs, high productivity obtains indoline-like derivative I, I and II is as follows for its structural formula:
。
2. synthetic method according to claim 1, is characterized in that, the R in described structural formula I and II 1, R 2, R 3, R 4, X substituting group is defined as follows respectively: wherein R 1for one on phenyl ring 3,4,5,6 replace or two replacement H, Br, Cl, I, SO 3h, C (CH 3) 3, CH 3, OCH 3, Py, Ph, Cy, 4-H 3cOC 6h 4, C 6h 5one in S, wherein disubstituted group can identical also can be different; When X is C, R 2for H, CH 3, CH 2cH 2cH 3, CH 2cH 2cl, OCH 3, OC (CH 3) 3, C (CH 3) 3, Bn, Py, Cy, Ph, C 4h 4s, CH 2cHPh, 2,6-di-F-C 6h 3, 2-F 3c-C 6h 4, 2-H 3c-C 6h 4, 2,6-di-CH 3-C 6h 3, 2,6-diCH 3o-C 6h 3, CHCH 2, 2-CH 3o-C 6h 4, C 6h 5, CHCHCH 3one; When X is S=O, R 2for 4-O 2nC 6h 4, 4-H 3cOC 6h 4one; R 3and R 4can be identical or different CH 3, CH 2oAc, CH 2oCH 3, CH 2sPh, CHCHCH 3, Ph, Cy, CH 2cH 3, one in Bn.
3. synthetic method according to claim 1, is characterized in that, catalyzer is that mantoquitaization is cuprous, cuprous bromide, cupric chloride, the one of cuprous chloride; The consumption of described catalyzer is 0.1-3 equivalent (be 1 equivalent with amide compound compounds, lower with); Described organic solvent is the one of DMSO, DMF, acetonitrile, toluene, parachlorotoluene, sym-trimethylbenzene; Described part is nitrogen Methylimidazole, PA, 2-minaline, benzo three nitrogen, 4-methylimidazole, triphenylphosphine, the one in pyridine, and wherein mole addition of part is 1-3 equivalent; Described oxygenant is hydrogen peroxide, t-butyl hydroperoxide, di-t-butyl peroxide, the one of tert-butyl peroxide isopropyl (base) benzene, and mole addition of oxygenant is 0.1-10 equivalent; The condition of described catalyzed reaction is: at 80-160 DEG C, react 4-40 hour.
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CN107474005A (en) * 2017-09-30 2017-12-15 台州学院 A kind of method for preparing the substituted indole quinoline derivants of N Ts 3
CN108947886A (en) * 2018-07-12 2018-12-07 江苏理工学院 A kind of sulfonylindoline compounds that more chloromethyls replace and its synthetic method and application
CN108947886B (en) * 2018-07-12 2021-05-18 江苏理工学院 Polychlorinated methyl substituted indoline compound and synthetic method and application thereof

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