CN109879881A - A kind of spiral shell [indoline -3,1`- pyrazolo [1,2- α] pyrazoles] analog derivative and its synthetic method - Google Patents
A kind of spiral shell [indoline -3,1`- pyrazolo [1,2- α] pyrazoles] analog derivative and its synthetic method Download PDFInfo
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- CN109879881A CN109879881A CN201910208351.4A CN201910208351A CN109879881A CN 109879881 A CN109879881 A CN 109879881A CN 201910208351 A CN201910208351 A CN 201910208351A CN 109879881 A CN109879881 A CN 109879881A
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Abstract
The present invention provides a kind of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative and its synthetic methods, belong to compound synthesis technical field.The copper carbonate of catalytic amount is added in equipped with the container for replacing (E) -5- oxo -2- (2- oxindole -3- subunit) pyrazolidine -2--1- compound class, substitution alkynes ester type compound, it is stirred under 25 DEG C -100 DEG C of reaction temperature, it filters after reaction, filtrate water or saturated common salt solution washing, then it is extracted with organic solvent, it is dry, vacuum distillation concentration removes solvent, crude product is through pillar layer separation, up to target product 6', 7'- dihydro 5'H spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] -2,5' diketone derivative.The present invention has many advantages, such as that reaction substrate wide adaptability, reaction condition are mild, regioselective is good, yield is high.
Description
Technical field
The invention belongs to organic synthesis technical fields, are related to a kind of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrrole
Azoles] analog derivative and its synthetic method.
Background technique
Heterocyclic compound has extremely wide application in Field of Drug Discovery, according to statistics, the medicine clinically used at present
Object has 90% or more to belong to heterocyclic compound.Obviously, heterocyclic compound occupies particularly important position in medicament research and development.Its
In, endogenous material isatin and its derivative can form hydrogen bond, electrostatic interaction, metal-chelating effect, Van der Waals force and π-π
Conjugation etc. a variety of non-covalent bond effects, have antibacterial, antitumor, AntiHIV1 RT activity, anti-malarial, anti-inflammatory, anti-oxidant, anticonvulsion, expelling parasite and
The multiple biological activities such as anti-TB, in field of medicinal chemistry by favor.In addition, certain isatin class compound such as smasani, Austria
Peace has been used for treating various diseases or is in clinical late conceptual phase for Buddhist nun, Sutent and Nintedanib.Isatin for
The more in addition extensive bioactivity in the site of modification and successful application clinically, so that isatin has become Pharmaceutical Chemist
The hot spot skeleton competitively studied.
Simultaneous with N, the heterocyclic molecular of N'- bicyclic pyrazolidinones equally has extensive important biomolecule activity, this kind of miscellaneous
The synthesis of toroidal molecule causes the very big concern of synthetic population.In many synthetic methods, the 1,3- of azomethine imines and alkynes
Dipolar Cycloaddition has been widely used as preparing N, the available strategy of N'- bicyclic pyrazolidinones structure.
Therefore this research will become a kind of with isatin skeleton in the 3 of isatin upper introducing N, N'- pyrazolidone
Novel 1,3- dipole body, then react with substituted alkynes ester to prepare 6', 7'- dihydro 5'H spiral shell [indoline -3,1'- pyrazolo
[1,2- α] pyrazoles] -2,5' diketone derivative, the biological activity test of compound provides material base thus.
Summary of the invention
In view of the above problems existing in the prior art, the purpose of the present invention is to provide a kind of spiral shell [indoline -3,1'-
Pyrazolo [1,2- α] pyrazoles] analog derivative and its synthetic method, this method has that reaction condition is mild, easy to operate, raw material is honest and clean
The advantages such as valence.
Object of the invention can be realized by the following technical scheme: a kind of spiral shell [indoline -3,1'- pyrazolo [1,2-
α] pyrazoles] analog derivative, which is characterized in that its structural formula is as follows:
Wherein R1 be 4- methyl, 4- ethyl, 4- isopropyl, 4- methoxyl group, 4- fluorine, 4- chlorine, 4- bromine, 4- itrile group, 4- amido,
4- nitro, 5- methyl, 5- ethyl, 5- isopropyl, 5- methoxyl group, 5- fluorine, 5- chlorine, 5- bromine, 5- itrile group, 5- amido, 5- nitro, 7-
It is any one in methyl, 7- ethyl, 7- isopropyl, 7- methoxyl group, 7- fluorine, 7- chlorine, 7- bromine, 7- itrile group, 7- amido, 7- nitro etc.
Kind；
R2 is in methyl formate base, group-4 ethyl formate, isopropyl formate base, t-butyl formate base, benzyl formate base etc.
Any one；
R3 is in hydrogen, methyl formate base, group-4 ethyl formate, isopropyl formate base, t-butyl formate base, benzyl formate base etc.
Any one；
R4 is any one in hydrogen, methyl etc.；
R5 is hydrogen, methyl, benzyl, methyl formate base, group-4 ethyl formate, isopropyl formate base, t-butyl formate base, formic acid
Any one in carbobenzoxy group, methanesulfonic acid ester group, p-methyl benzenesulfonic acid ester etc.；
A kind of synthetic method of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative, which is characterized in that
Comprising steps of equipped with substitution (E) -5- oxo -2- (2- oxindole -3- subunit) pyrazolidine -2--1- compound class, substitution
The copper carbonate of catalytic amount is added in the container of alkynes ester type compound, is stirred under 25 DEG C -100 DEG C of reaction temperature, reaction terminates
After filter, then filtrate water or saturated common salt solution washing are extracted with organic solvent, dry, vacuum distillation concentration removes molten
Agent, crude product is through pillar layer separation to get target product 6', 7'- dihydro 5'H spiral shell [indoline -3,1'- pyrazolo [1,2- α]
Pyrazoles] -2,5' diketone derivative, reaction equation is as follows:
The organic solvent is in methylene chloride, chloroform, acetonitrile, tetrahydrofuran, benzene,toluene,xylene etc.
Any one.
The catalyst is for Cu (OAc)2、CuCl2、Cu2O、CuCO3、CuCl、Cu(CF3SO3)2、CuI、Ag2In O etc.
It is one or more.
The dosage of the catalyst is (the E) -5- oxo -2- (2- oxindole -3- subunit) pyrazolidine -2--1-
The 5-20% equivalent of compound.
Described (E) -5- oxo -2- (2- oxindole -3- subunit) pyrazolidine -2--1- compound class replaces alkynes esters
Molar ratio between compound is 1:1.1.
Described (E) -5- oxo -2- (2- oxindole -3- subunit) pyrazolidine -2--1- compound class is selected from (E) -
2- (1- benzyl -4- methyl -2- oxindole -3- subunit) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl -4-
Fluoro- 2- oxindole -3- subunit) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (bromo- 2- oxindole -3- of 1- benzyl -4-
Subunit) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl -4- chloro-2-oxo indoles -3- subunit) -5- oxygen pyrazoles
Alkane -2--1- compound, (E) -2- (1- benzyl -5- methyl -2- oxindole -3- subunit) -5- oxygen pyrazolidine -2--1-ization
Object, (E) -2- (1- benzyl -5- chloro-2-oxo indoles -3- subunit) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl
The bromo- 2- oxindole -3- subunit of base -5-) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl -5- nitro -2- oxo
Indoles -3- subunit) -5- oxygen pyrazolidine -2--1- the compound, (Asia 1- benzyl -5- methoxyl group -2- oxindole -3- (E) -2-
Base) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl -5- trifluoromethyl -2- oxindole -3- subunit) -5- oxygen pyrrole
Any one in oxazolidine -2--1- compound etc..
The substitution alkynes ester type compound is selected from Methyl propiolate, ethyl propiolate, propine isopropyl propionate, propiolic acid
The tert-butyl ester, propine acid benzyl ester, butine dimethyl phthalate, butine diethyl phthalate, tetrolic acid diisopropyl ester, tetrolic acid di tert butyl carbonate, fourth
One of acetylenic acid dibenzyl ester etc..
The invention has the benefit that
It is provided by the present invention to prepare 6', 7'- dihydro with raw material multiple groups part one kettle way cheap and easy to get in mild environment
5'H spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] -2,5' diketone derivative, the selectivity and yield of product are all
It is very high, there is good prospects for commercial application.
Detailed description of the invention
Fig. 1 is the chemical equation of synthetic method in the present invention.
Fig. 2 is 1- benzyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,2-a]
Pyrazoles] -2'- carboxylic acid, ethyl ester1HNMR figure.
Fig. 3 is 1- benzyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,2-a]
Pyrazoles] -2'- carboxylic acid, ethyl ester13CNMR figure.
Specific embodiment
The present invention will be further described below with reference to examples, but protection scope of the present invention is not limited solely to implement
Example.
Figure of description 2 is 1- benzyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazoles
And [1,2-a] pyrazoles] -2'- carboxylic acid, ethyl ester1HNMR figure, attached drawing 3 are 1- benzyl -2,5'- dioxo -6', 7'- dihydro -5'H-
Spiral shell [indoline -3,1'- pyrazolo [1,2-a] pyrazoles] -2'- carboxylic acid, ethyl ester13CNMR figure obtains product for this method and provides
Certain foundation.
Replace 6', 7'- dihydro 5'H spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] -2,5' diketone derivative
Synthesis
As shown in Figure 1,6' provided by the invention, 7'- dihydro 5'H spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrrole
Azoles] -2,5' diketone derivative (I) synthesis step are as follows: in the reaction vessel be added 0.1mmol (E) -5- oxo -2- (2- oxygen
For indoles -3- subunit) (such as: (1- benzyl -4- methyl -2- oxindole -3- is sub- by (E) -2- for pyrazolidine -2--1- compound (II)
Base) -5- oxygen pyrazolidine -2--1- compound etc.), replace (III) 0.1~0.11mmol of alkynes ester, 5~20mol% of catalyst (to be based on
Compound (II)), 2~3ml solvent (such as: methylene chloride) then is added, 25-100 DEG C of reaction, after reaction, and filtering, solution
It is washed with water or saturated salt solution, is then extracted with organic solvent, dry, vacuum distillation concentration removes solvent, and crude product is through column
Chromatographic isolation or recrystallization are to get target product.
Embodiment 1
1- benzyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,2-a] pyrrole
Azoles] -2'- carboxylic acid, ethyl ester synthesis
(E) -2- (1- benzyl -2- oxindoles -3- subunit) -5- oxygen pyrazoles -2- of 1.0mmol is added in the reaction vessel
Then 2mL methylene chloride is added in -1- compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol%, anti-under the conditions of 50 DEG C
It answers, after reaction, filtering, solution is washed with water or saturated salt solution, then extracted with organic solvent, dry, vacuum distillation
Concentration removes solvent, and crude product is through pillar layer separation to get target product, yield 83%.
Embodiment 2
1- benzyl -5- methyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,2-
A] pyrazoles] -2'- carboxylic acid, ethyl ester synthesis
(E) -2- (1- benzyl -5- methyl -2- oxindoles -3- subunit) -5- oxygen pyrrole of 1.0mmol is added in the reaction vessel
Then 2mL chloroform, 50 DEG C of items are added in azoles -2--1- compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol%
It is reacted under part, after reaction, filtering, solution is washed with water or saturated salt solution, is then extracted with organic solvent, and it is dry, subtract
Distillation and concentration is pressed to remove solvent, crude product is through pillar layer separation to get target product, yield 78%.
Embodiment 3
1- benzyl -5- methoxyl group -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,
2-a] pyrazoles] -2'- carboxylic acid, ethyl ester synthesis
(E) -2- (1- benzyl -5- methoxyl group -2- oxindoles -3- subunit) -5- oxygen of 1.0mmol is added in the reaction vessel
Pyrazoles -2--1- compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol%, then be added 2mL methylene chloride, 50 DEG C
Under the conditions of react, after reaction, filtering, solution wash with water or saturated salt solution, then extracted with organic solvent, dry,
Vacuum distillation concentration removes solvent, and crude product is through pillar layer separation to get target product, yield 80%.
Embodiment 4
Bromo- 2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3, the 1'- pyrazolo [1,2-a] of 1- benzyl -5-
Pyrazoles] -2'- carboxylic acid, ethyl ester synthesis
(E) -2- (the bromo- 2- oxindoles -3- subunit of 1- benzyl -5-) -5- oxygen pyrrole of 1.0mmol is added in the reaction vessel
Then 2mL methylene chloride, 50 DEG C of items are added in azoles -2--1- compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol%
It is reacted under part, after reaction, filtering, solution is washed with water or saturated salt solution, is then extracted with organic solvent, and it is dry, subtract
Distillation and concentration is pressed to remove solvent, crude product is through pillar layer separation to get target product, yield 75%.
Embodiment 5
1- benzyl -5,7- dimethyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo
[1,2-a] pyrazoles] -2'- carboxylic acid, ethyl ester synthesis
(E) -2- (1- benzyl -5,7- dimethyl -2- oxindoles -3- subunit) -5- of 1.0mmol is added in the reaction vessel
Oxygen pyrazoles -2--1- compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol%, then be added 2mL methylene chloride, 50
It is reacted under the conditions of DEG C, after reaction, filtering, solution is washed with water or saturated salt solution, then extracted with organic solvent, is done
Dry, vacuum distillation concentration removes solvent, and crude product is through pillar layer separation to get target product, yield 78%.
Embodiment 6
Diethyl 1- benzyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,2-
A] pyrazoles] -2', the synthesis of 3'- dicarboxylic acids
(E) -2- (1- benzyl -2- oxindoles -3- subunit) -5- oxygen pyrazoles -2- of 1.0mmol is added in the reaction vessel
Then 2mL methylene chloride is added, under the conditions of 50 DEG C in -1- compound, the butine diethyl phthalate of 1.1mmol, the copper carbonate of 5mol%
Reaction, after reaction, filtering, solution are washed with water or saturated salt solution, are then extracted with organic solvent, dry, and decompression is steamed
It evaporates concentration and removes solvent, crude product is through pillar layer separation to get target product, yield 73%.
Embodiment 7
1- benzyl -7'- methyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,
2-a] pyrazoles] -2, the synthesis of-formic acid
(E) -2- (1- benzyl -2- oxindoles -3- subunit) -3- methyl -5- oxygen pyrrole of 1.0mmol is added in the reaction vessel
Then 2mL methylene chloride, 50 DEG C of items are added in azoles -2--1- compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol%
It is reacted under part, after reaction, filtering, solution is washed with water or saturated salt solution, is then extracted with organic solvent, and it is dry, subtract
Distillation and concentration is pressed to remove solvent, crude product is through pillar layer separation to get target product, yield 80%.
Embodiment 8
2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,2-a] pyrazoles] -2'- carboxylics
The synthesis of acetoacetic ester
(E) -5- oxo -2- (2- oxindoles -3- subunit) pyrazolidine -2--1- of 1.0mmol is added in the reaction vessel
Then compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol% are added 2mL methylene chloride, react under the conditions of 50 DEG C, instead
After answering, filtering, solution is washed with water or saturated salt solution, is then extracted with organic solvent, dry, and vacuum distillation concentration removes
Solvent is removed, crude product is through pillar layer separation to get target product, yield 65%.
Embodiment 9
1- methyl -2,5'- dioxo -6', 7'- dihydro -5'H- spiral shell [indoline -3,1'- pyrazolo [1,2-a] pyrrole
Azoles] -2'- carboxylic acid, ethyl ester synthesis
(E) -2- (1- methyl -2- oxindoles -3- subunit) -5- oxygen pyrazolidine -2- of 1.0mmol is added in the reaction vessel
Then 2mL methylene chloride is added in -1- compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol%, anti-under the conditions of 50 DEG C
It answers, after reaction, filtering, solution is washed with water or saturated salt solution, then extracted with organic solvent, dry, vacuum distillation
Concentration removes solvent, and crude product is through pillar layer separation to get target product, yield 75%.
Embodiment 10
2,5'- dioxo -1- (2- oxo -2- phenyl -1,2- ethyl) -6', 7'- dihydro -5'H- spiral shell [indoline -3,
1'- pyrazolo [1,2]-a] pyrazoles] -2'- t-butyl formate synthesis
(E) -2- (1- ((benzyloxy) carbonyl) -2- oxindoles -3- subunit) -5- of 1.0mmol is added in the reaction vessel
Then 2mL methylene chloride is added in oxygen pyrazolidine -2--1- compound, the ethyl propiolate of 1.1mmol, the copper carbonate of 5mol%,
It is reacted under the conditions of 50 DEG C, after reaction, filtering, solution is washed with water or saturated salt solution, then extracted with organic solvent, is done
Dry, vacuum distillation concentration removes solvent, and crude product is through pillar layer separation to get target product, yield 80%.
Specific embodiment described herein is only an example for the spirit of the invention.The neck of technology belonging to the present invention
The technical staff in domain can make various modifications or additions to the described embodiments or replace by a similar method
In generation, however, it does not deviate from the spirit of the invention or beyond the scope of the appended claims.
Claims (8)
1. a kind of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative, which is characterized in that its structural formula is such as
Under:
Wherein R1 is 4- methyl, 4- ethyl, 4- isopropyl, 4- methoxyl group, 4- fluorine, 4- chlorine, 4- bromine, 4- itrile group, 4- amido, 4- nitre
Base, 5- methyl, 5- ethyl, 5- isopropyl, 5- methoxyl group, 5- fluorine, 5- chlorine, 5- bromine, 5- itrile group, 5- amido, 5- nitro, 7- first
It is any one in base, 7- ethyl, 7- isopropyl, 7- methoxyl group, 7- fluorine, 7- chlorine, 7- bromine, 7- itrile group, 7- amido, 7- nitro etc.
Kind；
R2 is any in methyl formate base, group-4 ethyl formate, isopropyl formate base, t-butyl formate base, benzyl formate base etc.
It is a kind of；
R3 is appointing in hydrogen, methyl formate base, group-4 ethyl formate, isopropyl formate base, t-butyl formate base, benzyl formate base etc.
It anticipates one kind；
R4 is any one in hydrogen, methyl etc.；
R5 is hydrogen, methyl, benzyl, methyl formate base, group-4 ethyl formate, isopropyl formate base, t-butyl formate base, benzyl formate
Any one in base, methanesulfonic acid ester group, p-methyl benzenesulfonic acid ester etc..
2. a kind of synthetic method of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative, which is characterized in that packet
Include step: equipped with substitution (E) -5- oxo -2- (2- oxindole -3- subunit) pyrazolidine -2--1- compound class, substitution alkynes
The copper carbonate of catalytic amount is added in the container of ester type compound, is stirred under 25 DEG C -100 DEG C of reaction temperature, after reaction
Filtering, filtrate water or saturated common salt solution washing, are then extracted with organic solvent, dry, and vacuum distillation concentration removes solvent,
Crude product is through pillar layer separation to get target product 6', 7'- dihydro 5'H spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrrole
Azoles] -2,5' diketone derivative, reaction equation is as follows:
3. a kind of synthesis of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative according to claim 2
Method, which is characterized in that the organic solvent is selected from methylene chloride, chloroform, acetonitrile, tetrahydrofuran, benzene, toluene, two
Any one in toluene etc..
4. a kind of synthesis of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative according to claim 2
Method, which is characterized in that the catalyst is for Cu (OAc)2、CuCl2、Cu2O、CuCO3、CuCl、Cu(CF3SO3)2、CuI、
Ag2One of O etc. or a variety of.
5. a kind of 6' according to claim 2,7'- dihydro 5'H spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] -
The synthetic method of 2,5' diketone derivatives, which is characterized in that the dosage of the catalyst is (the E) -5- oxo -2- (2-
Oxindole -3- subunit) pyrazolidine -2--1- compound 5-20% equivalent.
6. a kind of synthesis of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative according to claim 2
Method, which is characterized in that described (E) -5- oxo -2- (2- oxindole -3- subunit) pyrazolidine -2--1- compound class takes
It is 1:1.1 for the molar ratio between alkynes ester type compound.
7. a kind of synthesis of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative according to claim 2
Method, which is characterized in that described (E) -5- oxo -2- (2- oxindole -3- subunit) pyrazolidine -2--1- compound class is
Selected from (E) -2- (1- benzyl -4- methyl -2- oxindole -3- subunit) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1-
The fluoro- 2- oxindole -3- subunit of benzyl -4-) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (bromo- 2- oxo of 1- benzyl -4-
Indoles -3- subunit) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl -4- chloro-2-oxo indoles -3- subunit) -5-
Oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl -5- methyl -2- oxindole -3- subunit) -5- oxygen pyrazolidine -2--
1- compound, (E) -2- (1- benzyl -5- chloro-2-oxo indoles -3- subunit) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1-
The bromo- 2- oxindole -3- subunit of benzyl -5-) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl -5- nitro -2- oxygen
For indoles -3- subunit) -5- oxygen pyrazolidine -2--1- the compound, (Asia 1- benzyl -5- methoxyl group -2- oxindole -3- (E) -2-
Base) -5- oxygen pyrazolidine -2--1- compound, (E) -2- (1- benzyl -5- trifluoromethyl -2- oxindole -3- subunit) -5- oxygen pyrrole
Any one in oxazolidine -2--1- compound etc..
8. a kind of synthesis of spiral shell [indoline -3,1'- pyrazolo [1,2- α] pyrazoles] analog derivative according to claim 2
Method, which is characterized in that the substitution alkynes ester type compound is selected from Methyl propiolate, ethyl propiolate, propiolic acid isopropyl
Ester, propine tert-butyl acrylate, propine acid benzyl ester, butine dimethyl phthalate, butine diethyl phthalate, tetrolic acid diisopropyl ester, tetrolic acid two
One of the tert-butyl ester, tetrolic acid dibenzyl ester etc..
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| CN112300181A (en) * | 2020-01-21 | 2021-02-02 | 新乡学院 | Diketone skeleton compound and its preparing method and use |
| CN114516881A (en) * | 2022-03-08 | 2022-05-20 | 贵州大学 | Azacyclocarbene-catalyzed chiral compound containing pyrazolopyran skeleton and preparation method thereof |
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| CN112300181A (en) * | 2020-01-21 | 2021-02-02 | 新乡学院 | Diketone skeleton compound and its preparing method and use |
| CN112300181B (en) * | 2020-01-21 | 2022-11-04 | 新乡学院 | Diketone framework compound and its preparation method and application |
| CN114516881A (en) * | 2022-03-08 | 2022-05-20 | 贵州大学 | Azacyclocarbene-catalyzed chiral compound containing pyrazolopyran skeleton and preparation method thereof |
| CN114516881B (en) * | 2022-03-08 | 2023-07-25 | 贵州大学 | Azacyclo-carbene catalyzed pyrazolopyran skeleton-containing chiral compound and preparation method thereof |
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