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Multi-substituted dihydropyridine-4-one compounds and their preparation methods and applications

A compound and substituent technology, applied in the field of multi-substituted dihydropyridine-4-one compounds, can solve the problems of low yield, complex operation, poor selectivity, etc., and achieve high yield, easy separation and purification, and stable separation and purification Effect

Inactive Publication Date: 2016-01-27
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, the existing synthetic methods still have limitations such as low yield, complicated operation, and poor selectivity, and it is necessary to develop new synthetic methods with a dihydropyridin-4-one skeleton structure

Method used

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  • Multi-substituted dihydropyridine-4-one compounds and their preparation methods and applications
  • Multi-substituted dihydropyridine-4-one compounds and their preparation methods and applications
  • Multi-substituted dihydropyridine-4-one compounds and their preparation methods and applications

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1, the dihydropyridin-4-ketone compound shown in the general structural formula of preparation formula Ia

[0041] The reaction formula is as follows:

[0042]

[0043] The specific preparation method is:

[0044] 1) Under the protection of nitrogen, in a dry and clean 50mL round bottom flask, add magnetons, the functionalized enamide (79.6mg, 0.3mmol) shown in the formula IIa, and the isonitrile (47.9 mg) shown in the formula IIIa mg, 0.36mmol), additive Molecular sieves (300 mg), then add 15 mL of molecular sieve-dried solvent acetonitrile, and add catalyst anhydrous zinc trifluoromethanesulfonate Zn (OTf) after dissolving 2 (109.1mg, 0.3mmol), after a heterogeneous reaction at room temperature 25°C for 10h, TLC analysis showed that the starting material IIa was completely consumed.

[0045]2) Add acid-binding agent triethylamine (100uL, 0.72mmol) and benzoyl chloride (84uL, 0.72mmol) to the reaction system, stir at room temperature for 2h, then add ...

Embodiment 2

[0054] Embodiment 2, the dihydropyridine-4-ketone compounds shown in the general structural formula of preparation formula Ib

[0055] The reaction formula is as follows:

[0056]

[0057] The specific preparation method is:

[0058] 1) Under the protection of nitrogen, in a dry and clean 50mL round bottom flask, add magnetons, functionalized enamide (85.0mg, 0.3mmol) shown in the formula IIb structural formula, and isocyanide (47.9 mg) shown in the structural formula IIIa mg, 0.36mmol), Molecular sieves (300mg) were added to molecular sieve-dried acetonitrile 15mL, and after dissolution, anhydrous zinc trifluoromethanesulfonate (109.1mg, 0.3mmol) was added, and heterogeneous reaction was carried out at room temperature for 7h. TLC analysis showed that the raw material IIb was completely consumed.

[0059] 2) Add triethylamine (100uL, 0.72mmol) and benzoyl chloride (84uL, 0.72mmol) to the reaction system, stir at room temperature for 2h, then add concentrated hydrochlori...

Embodiment 3

[0068] Embodiment 3, the dihydropyridine-4-ketone compound shown in the general structural formula of preparation formula Ic

[0069] The reaction formula is as follows:

[0070]

[0071] The specific preparation method is:

[0072] 1) Under the protection of nitrogen, in a dry and clean 50mL round bottom flask, add magnetons, functionalized enamide (90.0mg, 0.3mmol) shown in the formula IIc structural formula, and isocyanide (47.9 mg) shown in the formula IIIa structural formula mg, 0.36mmol), Molecular sieves (300 mg) were added, and 15 mL of molecular sieve-dried acetonitrile was added. After dissolving, anhydrous zinc trifluoromethanesulfonate (109.1 mg, 0.3 mmol) was added. After reacting at room temperature for 8 h, TLC analysis showed that the raw material IIc was completely consumed.

[0073] 2) Add triethylamine (100uL, 0.72mmol) and benzoyl chloride (84uL, 0.72mmol) to the reaction system, stir at room temperature for 2h, then add concentrated hydrochloric acid...

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Abstract

The invention discloses a multi-substituted dihydropyridine-4-ketone compound, a preparation method and an application thereof, wherein a structure general formula of the compound is represented as formula I. The preparation method includes a step of carrying out an intermolecular cascade reaction between a functionalized alkenyl amide and isonitrile in an organic solution with a Lewis acid being a catalyst to efficiently obtain the dihydropyridine-4-ketone compound. By means of the method, multi-substituted dihydropyridine-4-ketone compounds having various substituent groups can be synthesized, wherein the multi-substituted dihydropyridine-4-ketone compounds having various substituent groups cannot be synthesized by other methods. The method is simple in operation and is high in yield. A product is easy to purify. The method has a good application prospect.

Description

technical field [0001] The invention relates to a multi-substituted dihydropyridine-4-one compound and its preparation method and application. Background technique [0002] Dihydropyridine-4-ones are abundant in natural products and physiologically active compounds. In addition, it can also be used as an organic reaction intermediate to participate in a series of different chemical transformations (Georg.G.I.; J.Org.Chem.2010, 75, 6793-6805.), thereby synthesizing nitrogen-containing heterocyclic compounds with diverse structures Or natural products. [0003] For the synthesis of dihydropyridine-4-ketones, existing synthetic methods mainly involve hetero Diels-Alder reaction, addition of pyridinium salt and Grignard reagent, cyclization reaction of aminoacetylenone etc. (Alaimo, P.J.Org.Lett 2008, 10, 5111-5114; Comins, D.L.J.Am.Chem.Soc. 1994, 116, 4719-4728; Georg, G.I.J.Am.Chem.Soc. 2006, 128, 8702-8703.). Nevertheless, the existing synthetic methods still have limitat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/86A61K31/4418A61K31/4412A61P35/00
CPCC07D211/86
Inventor 王梅祥雷川虎王德先
Owner INST OF CHEM CHINESE ACAD OF SCI