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Method used for preparing pyrrolo[3, 2,1-ij] quinolinone compound

A compound and quinolinone technology, applied in the field of organic chemical synthesis, can solve the problems of low reaction yield and low yield, and achieve the effects of high yield, wide substrate applicability and good industrial application prospects

Active Publication Date: 2019-06-18
INST OF CHEM CHINESE ACAD OF SCI
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Problems solved by technology

[0003] The methods for preparing pyrrolo[3,2,1-ij]quinolinone compounds in the prior art mainly include: Org.Biomol.Chem., 2015, 13, 9276-9284 discloses that under the action of rhodium catalyst, acylindine The reaction of indoline and alkyne to generate pyrroloquinolinone compound, but the application of zinc reagent in the reaction is not involved, the reaction yield is generally low (figure 1 ); Org.Lett.2015,17,1481-1484 also discloses the reaction of acyl indoline and alkyne under the effect of rhodium catalyst to generate pyrroloquinolinone compound, but does not involve aminomethyl zinc reagent in The application in the reaction, its yield is also generally not high ( figure 2 )

Method used

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  • Method used for preparing pyrrolo[3, 2,1-ij] quinolinone compound
  • Method used for preparing pyrrolo[3, 2,1-ij] quinolinone compound
  • Method used for preparing pyrrolo[3, 2,1-ij] quinolinone compound

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preparation example Construction

[0051] According to one embodiment of the present invention, a preparation method of a pyrrolo[3,2,1-ij]quinolinone compound is disclosed, the preparation method comprising the following steps:

[0052] In the presence of catalyst, Lewis acid and zinc reagent, the indoline compound shown in formula II and the alkyne shown in formula III undergo C-H bond activation / C-N bond cleavage reaction to obtain pyrrolo[3, 2,1-ij] quinolinone compounds;

[0053]

[0054] in,

[0055] R 1 independently represent mono-substitution, di-substitution, tri-substitution, tetra-substitution or no substitution;

[0056] R 1 Each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkane having 1-20 carbon atoms Base, aralkyl group having 7-30 carbon atoms, alkoxy group having 1-20 carbon atoms, aryloxy group having 6-30 carbon atoms, aryl group having 6-30 carbon atoms, having Alky...

Embodiment 1

[0073] according to image 3 The route diagram shown prepares 5,6-diphenyl-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (Formula I-a)

[0074] into a 25mL Schlenk bottle under N 2 Under the protection of N,N-diphenyl-1H-indoline-1-carboxamide (0.5mmol, 157.2mg), 1,2-diphenylacetylene (1.25mmol, 222.8mg), Re 2 (CO) 10 (0.025mmol, 16.3mg), a mixture of zinc trifluoromethanesulfonate (0.15mmol, 54.5mg), aminomethylzinc (0.075mmol, 37.3mg) and anhydrous toluene (0.625mL) was heated to 150°C for 48h, After the reaction was completed, the reaction solution was diluted with DCM and filtered through a thin layer of celite, and the thin layer of silica gel was washed with EA. After the filtrate was concentrated, it was separated by column chromatography (eluent: petroleum ether: ethyl acetate = 2 / 1, v / v) to obtain 124.7 mg of the target product (Formula I-a), with a yield of 77%.

[0075] The target product is characterized as follows: 1 H NMR (500MHz, CDCl3): δ7.34(d, J=6.8Hz, ...

Embodiment 2

[0077] according to Figure 4 The route diagram shown prepares 8-methyl-5,6-diphenyl-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (Formula I-b)

[0078] into a 25mL Schlenk bottle under N 2 Under the protection of 5-methyl-N,N-diphenyl-1H-indoline-1-carboxamide (0.5mmol, 164.2mg), 1,2-diphenylacetylene (1.25mmol, 222.8mg ), Re 2 (CO) 10 (0.025mmol, 16.3mg), a mixture of zinc trifluoromethanesulfonate (0.15mmol, 54.5mg), aminomethylzinc (0.075mmol, 37.3mg) and anhydrous toluene (0.625mL) was heated to 150°C for 48h, After the reaction was completed, the reaction solution was diluted with DCM and filtered through a thin layer of celite, and the thin layer of silica gel was washed with EA. After the filtrate was concentrated, it was separated by column chromatography (eluent: petroleum ether: ethyl acetate = 2 / 1, v / v) to obtain 123.4 mg of the target product (Formula I-b), with a yield of 73%.

[0079] The target product is characterized as follows: 1 H NMR (500MHz, CDCl3...

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and more specifically relates to a method used for preparing a pyrrolo[3, 2,1-ij] quinolinone compound. The method comprisesfollowing steps: in the presence of a catalyst, a Lewis acid, and an zinc reagent, an indoline compound represented by formula II and an alkyne represented by formula III are subjected to C-H bond activation / C-N bond rupture reaction so as to obtain the pyrrolo[3, 2,1-ij] quinolinone compound represented by formula. According to the method, indoline is reacted with the alkyne in the presence of the catalyst, the Lewis acid, and the zinc reagent in a solvent, so that synthesis of the pyrrolo[3, 2,1-ij] quinolinone compound is realized.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for preparing pyrrolo[3,2,1-ij]quinolinone compounds. Background technique [0002] Pyrrolo[3,2,1-ij]quinolinones are important nitrogen-containing heterocyclic compounds that widely exist in nature. It has a variety of biological activities and special chemical properties, and can be used as the active structural unit of many natural products and drugs, and has important research value and application prospects in the fields of organic synthesis, medicine and chemical industry. [0003] The methods for preparing pyrrolo[3,2,1-ij]quinolinone compounds in the prior art mainly include: Org.Biomol.Chem., 2015, 13, 9276-9284 discloses that under the action of a rhodium catalyst, acylindine The reaction of indoline and alkyne to generate pyrroloquinolinone compound, but the application of zinc reagent in the reaction is not involved, the reaction yield is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06
Inventor 王从洋杨芸辉
Owner INST OF CHEM CHINESE ACAD OF SCI
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