CN112624957A - Synthetic method of 3-alkyl isoindolinone derivatives - Google Patents

Synthetic method of 3-alkyl isoindolinone derivatives Download PDF

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CN112624957A
CN112624957A CN202110159709.6A CN202110159709A CN112624957A CN 112624957 A CN112624957 A CN 112624957A CN 202110159709 A CN202110159709 A CN 202110159709A CN 112624957 A CN112624957 A CN 112624957A
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cyanobenzaldehyde
trifluoromethanesulfonate
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李阳
何柳
李剑
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Jiangsu Food and Pharmaceutical Science College
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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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Abstract

The invention discloses a synthesis process of a 3-alkyl isoindolinone derivative, and relates to the fields of natural products with biological activity, agricultural chemicals and medicines. The raw materials are o-cyanobenzaldehyde derivatives, terminal alkyne and diphenyl iodonium trifluoromethanesulfonate, copper trifluoromethanesulfonate is used as a catalyst, trifluoromethanesulfonic acid is used as an additive, and the reaction is carried out in an o-dichloroethane solution at 110 ℃ to obtain the 3-alkyl isoindolinone derivatives. The 3-alkyl isoindolinone derivative can be obtained by reacting for 2 hours at 110 ℃ by using the method provided by the invention, and the yield is 52-91%. The reaction adopts simple and easily obtained raw materials, and the 3-alkyl isoindolinone derivatives are synthesized by a one-pot method, thereby providing a simple, convenient, efficient and green new synthesis method for synthesizing the derivatives.

Description

Synthetic method of 3-alkyl isoindolinone derivatives
Technical Field
The invention relates to a synthesis process for preparing 3-alkyl isoindolinone, belonging to the technical field of drug synthesis and active natural products.
Background
Nitrogen-containing heterocyclic backbones are widely found in biologically active natural products and pharmaceutical chemistry. Among the various nitrogen-containing compounds, 3-alkylisoindolinones are an important class of biologically active and therapeutically potential building blocks, such as paqinlong, paglong, JM1232, zopiclone, etc. At present, the synthetic methods reported in the literature have the defects that the reaction needs to synthesize the starting raw materials step by step, the yield is not high, the conditions are harsh, toxic or flammable reagents need to be used in the preparation process, and the like, so that the development of a simple, efficient and green synthetic method of the isoindolinone derivatives still has important significance.
We used o-cyanobenzaldehyde derivatives, terminal alkynes, diphenyliodonium trifluoromethanesulfonate and the additive trifluoromethanesulfonic acid to react at 110 ℃ under the catalysis of copper trifluoromethanesulfonate to give a series of 3-alkylisoindolinone derivatives.
Disclosure of Invention
The technical problem solved by the invention is to provide a method for synthesizing a 3-alkyl isoindolinone derivative by using an o-cyanobenzaldehyde derivative, terminal alkyne and diphenyl iodonium trifluoromethanesulfonate as raw materials through a one-pot tandem reaction under the catalysis of copper. The method has the advantages of simple and easily obtained raw materials, simple and convenient operation and high substrate universality.
The invention adopts the following technical scheme: a method for synthesizing isoindolinone by copper catalysis is developed, wherein o-cyanobenzaldehyde derivatives, terminal alkyne and diphenyl iodonium trifluoromethanesulfonate are used as raw materials, a proper amount of solvent is added under the catalysis of trifluoromethanesulfonic acid additive and copper trifluoromethanesulfonate, and then the raw materials are stirred and reacted for 2 hours at 110 ℃ under the air condition to generate 3-alkyl isoindolinone derivatives.
The molar ratio of the raw materials is O-cyanobenzaldehyde derivative, terminal alkyne and diphenyl iodonium trifluoromethanesulfonate =1:2: 1.5.
The additive is trifluoromethanesulfonic acid, and the amount of the trifluoromethanesulfonic acid is 1.5 equivalents based on the moles of the o-cyanobenzaldehyde derivative.
The catalyst is copper trifluoromethanesulfonate, and the dosage of the copper trifluoromethanesulfonate is 10% mmol of the mol number of the o-cyanobenzaldehyde derivative.
The above-mentioned o-cyanobenzaldehyde derivative may be 2-cyanobenzaldehyde, 5-fluoro-2-formylbenzonitrile, 5-methoxy-2-formylbenzonitrile, 5-chloro-2-formylbenzonitrile, etc.
The alkyne at the tail end of the raw material is phenylacetylene, 4-methylphenylacetylene, 4-fluorophenylacetylene, 4-chlorophenylacetylene, 4-bromophenylacetylene, 4-trifluoromethylphenylacetylene, 4-nitrophenylacetylene, 4-methylphenylacetylene, 2-methylphenylacetylene, naphthylacetylene, 2,3,4, 5-tetrafluorophenylacetylene, 2-ethynylthiophene and the like.
The above-mentioned starting diphenyliodonium trifluoromethanesulfonate R group may be R =4-H, 4-F, 4-CF3，4-Br，4-Cl，4-CH34-OMe, etc.
The reaction process and the structural formula of the obtained product are as follows:
Figure 181708DEST_PATH_IMAGE001
the post-reaction treatment is simple and convenient, and the pure 3-alkyl isoindolinone derivative can be obtained by using a mixed solvent of petroleum ether and ethyl acetate as an eluent only by recrystallization or a simple column chromatography separation method. The synthesized compound adopts1H NMR and13c NMR characterization, and the spectrogram data is matched with the structure.
The invention has the beneficial effects that: 3-alkylisoindolinones are important molecules with pharmaceutical activity and have wide application in the fields of natural products, agrochemicals and medicines. The method is characterized in that o-cyanobenzaldehyde derivatives, terminal alkyne and diphenyl iodonium trifluoromethanesulfonate are used as raw materials for the first time, trifluoromethanesulfonic acid is used as an additive, and a series of 3-alkyl isoindolinone is prepared by a copper-catalyzed one-pot method, wherein the yield is 52-91%. Three reaction substrates, namely o-cyanobenzaldehyde, terminal alkyne and diphenyl iodonium trifluoromethanesulfonate, are easy to expand, and the reaction universality is good.
Detailed Description
Example 1
O-cyanobenzaldehyde (1 mmol), phenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to obtain 4a in 79% yield.1H NMR (400 MHz, CDCl3) δ 7.95-7.92 (m, 1H), 7.87-7.85 (m, 2H), 7.60-7.51 (m, 8H), 7.46-7.41 (m, 2H), 5.96 (dd, J = 9.4, 3.0 Hz, 1H), 3.52 (dd, J = 17.8, 3.0 Hz, 1H), 3.27-3.19 (m, 1H). 13C NMR (125 MHz, CDCl3) δ 197.5, 166.9, 145.0, 136.2, 135.7, 133.9, 132.6, 132.4, 131.5, 128.8, 128.1, 124.3, 123.2, 118.6, 56.7, 41.8。
Example 2
O-cyanobenzaldehyde (1 mmol), 4-fluorophenylacetylene (2 mmol),bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were charged in a 15mL pressure-resistant tube, stirred at 110 ℃ and reacted for 2 hours, and the product was chromatographed on a silica gel column to give 4b in 75% yield.1H NMR (400 MHz, CDCl3) δ 7.95-7.88 (m, 3H), 7.55-7.52 (m, 7H), 7.12 (t, J = 8.2 Hz, 2H), 5.96-5.94 (m, 1H), 3.49 (dd, J = 10.0, 3.0 Hz, 1H), 3.23-3.17 (m, 1H). 13C NMR (125 MHz, CDCl3) δ 195.8, 167.2, 165.5 (d, J = 218.9 Hz), 144.9, 135.7, 132.6, 132.4, 131.5, 130.8 (d, J = 9.6 Hz), 128.9, 124.4 (d, J = 17.2 Hz), 123.1, 118.7, 115.9 (d, J = 21.9 Hz), 56.7, 41.7. 19F NMR (282 MHz, CDCl3) δ -103.4. HRMS (ESI) calcd for C22H16BrFNO2 ([M+H]+): 424.0343 found 424.0338。
Example 3
O-cyanobenzaldehyde (1 mmol), 4-chlorophenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4c in 69% yield.1H NMR (400 MHz, CDCl3) δ 7.95 (d, J = 7.2 Hz, 1H), 7.81 (d, J = 8.2 Hz, 2H), 7.56-7.49 (m, 7H), 7.42 (d, J = 8.2 Hz, 2H), 5.96-5.94 (m, 1H), 3.52-3.47 (m, 1H), 3.23-3.17 (m, 1H). 13C NMR (125 MHz, CDCl3) δ 196.3, 166.8, 144.8, 140.5, 135.7, 134.5, 132.7, 132.4, 131.5, 129.1, 128.9, 123.1, 118.7, 56.6, 41.8. HRMS (ESI) calcd for C22H16BrClNO2 ([M+H]+): 440.0047 found 440.0039。
Example 4
O-cyanobenzaldehyde (1 mmol), 4-bromophenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4d in 65% yield.
Example 5
O-cyanobenzaldehyde (1 mmol), 4-trifluoromethylphenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were charged in a 15mL pressure tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4e in 65% yield.
Example 6
O-cyanobenzaldehyde (1 mmol), 4-nitrophenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4f in a yield of 72%.
Example 7
O-cyanobenzaldehyde (1 mmol), 4-methylphenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were charged in a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4g of 81% yield.
Example 8
O-cyanobenzaldehyde (1 mmol), 2-methylphenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give a yield of 79% for 4 hours.
Example 9
O-cyanobenzaldehyde (1 mmol), naphthylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to obtain 4i in 85% yield.
Example 10
O-cyanobenzaldehyde (1 mmol), 2,3,4, 5-tetrafluorophenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ and reacted for 2 hours, and the product was separated by silica gel column chromatography to give 4j in 75% yield.
Example 11
O-cyanobenzaldehyde (1 mmol), 2-thiophenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4k in 52% yield.
Example 12
O-cyanobenzaldehyde (1 mmol), phenylacetylene (2 mmol), diphenyliodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4l of 91% yield.
Example 13
O-cyanobenzaldehyde (1 mmol), phenylacetylene (2 mmol), bis (4-fluorobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to obtain 4m of 78% yield.
Example 14
O-cyanobenzaldehyde (1 mmol), phenylacetylene (2 mmol), bis (4-chlorobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to obtain 4n in 79% yield.
Example 15
O-cyanobenzaldehyde (1 mmol), phenylacetylene (2 mmol), bis (4-toluene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were charged in a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to obtain 4 ℃ in 82% yield.
Example 16
O-cyanobenzaldehyde (1 mmol), phenylacetylene (2 mmol), bis (4-benzyl ether) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to obtain 4p in 83% yield.
Example 17
O-cyanobenzaldehyde (1 mmol), phenylacetylene (2 mmol), bis (4-trifluorotoluene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were charged in a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to obtain 4q of 70% yield.
Example 18
5-fluoro-2-acylbenzonitrile (1 mmol), phenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4r in 66% yield.
Example 19
5-chloro-2-acylbenzonitrile (1 mmol), phenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were charged in a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give a yield of 4s of 76%.
Example 20
5-methoxy-2-acylbenzonitrile (1 mmol), phenylacetylene (2 mmol), bis (4-bromobenzene) iodonium trifluoromethanesulfonate (1.5mmol), trifluoromethanesulfonic acid (1.5mmol), copper trifluoromethanesulfonate (10 mmol%) and 2mL of o-dichloroethane were added to a 15mL pressure-resistant tube, stirred at 110 ℃ for 2 hours, and subjected to silica gel column chromatography to give 4t of 79% yield.

Claims (8)

1. A preparation method of 3-alkyl isoindolinone is characterized in that under the catalysis of copper, o-cyanobenzaldehyde derivatives, terminal alkyne and diphenyl iodonium trifluoromethanesulfonate are used as raw materials, a proper amount of catalyst, additive and solvent are added, and the reaction is carried out for 2 hours under the condition of air and at the temperature of 110 ℃ under stirring to generate the 3-alkyl isoindolinone derivatives.
2. The process of claim 1, wherein the catalyst is copper triflate.
3. The process of claim 1, wherein the additive is trifluoromethanesulfonic acid.
4. The method for preparing 3-alkylisoindolinone according to claim 1, wherein the molar ratio of the raw materials is ortho-cyanobenzaldehyde derivative, terminal alkyne, diphenyl iodonium trifluoromethanesulfonate =1:2: 1.5.
5. A process for the preparation of a 3-alkylisoindolinone according to claim 1, characterized in that said solvent is 1, 2-dichloroethane; the amount of the solvent used was 2mL/mmol of o-cyanobenzaldehyde.
6. The method of claim 1, wherein the o-cyanobenzaldehyde derivative is selected from the group consisting of 2-cyanobenzaldehyde, 5-fluoro-2-formylbenzonitrile, 5-methoxy-2-formylbenzonitrile and 5-chloro-2-formylbenzonitrile.
7. The method of claim 1, wherein the starting terminal alkyne is phenylacetylene, 4-methylphenylacetylene, 4-fluorophenylacetylene, 4-chlorophenylacetylene, 4-bromophenylacetylene, 4-trifluoromethylphenylacetylene, 4-nitrophenylacetylene, 4-methylphenylacetylene, 2-methylphenylacetylene, naphthylacetylene, 2,3,4, 5-tetrafluorophenylacetylene, 2-ethynylthiophene, etc.
8. The process of claim 1, wherein the R group of the diphenyliodonium trifluoromethanesulfonate is R =4-H, 4-F, 4-CF3，4-Br，4-Cl，4-CH34-OMe, etc.
CN202110159709.6A 2021-02-05 2021-02-05 Synthetic method of 3-alkyl isoindolinone derivatives Pending CN112624957A (en)

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN113214224A (en) * 2021-05-10 2021-08-06 成都大学 Preparation method of polysubstituted 3-methylene isoindolinone derivative

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CN107056677A (en) * 2017-06-19 2017-08-18 常州大学 A kind of synthetic method of the xylylenimine quinoline ketone derivatives of 3 alkyl 2,3
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CN104876850A (en) * 2015-06-01 2015-09-02 常州大学 Isoindolinone derivative synthesis method
CN107056677A (en) * 2017-06-19 2017-08-18 常州大学 A kind of synthetic method of the xylylenimine quinoline ketone derivatives of 3 alkyl 2,3
CN107382820A (en) * 2017-06-29 2017-11-24 常州大学 A kind of synthetic method of 3 arylisoindole derivative

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113214224A (en) * 2021-05-10 2021-08-06 成都大学 Preparation method of polysubstituted 3-methylene isoindolinone derivative
CN113214224B (en) * 2021-05-10 2023-10-27 成都大学 Preparation method of polysubstituted 3-methylene isoindolinone derivative

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