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Novel synthetic method of 3,4-dihydroisoquinolin-1-one and isoindolin-1-one derivatives

A technology of dihydroisoquinoline and synthesis method, which is applied in 3 fields, can solve problems such as unstable reactants, harsh reaction conditions, and complicated preparation process, and achieve the effects of high reaction yield, simple operation, and high application value

Active Publication Date: 2018-03-09
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above method has the disadvantages of using transition metal catalysis, requiring special or unstable reactants, complicated preparation process, and harsh reaction conditions.

Method used

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  • Novel synthetic method of 3,4-dihydroisoquinolin-1-one and isoindolin-1-one derivatives
  • Novel synthetic method of 3,4-dihydroisoquinolin-1-one and isoindolin-1-one derivatives
  • Novel synthetic method of 3,4-dihydroisoquinolin-1-one and isoindolin-1-one derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] In a 250mL round-bottomed flask, add potassium tert-butoxide (0.336g, 3.0mmol), III-a (2.233g, 10.0mmol), N,N-dimethylformamide (70.0mL), under nitrogen protection at 120°C The reaction was carried out for 20 hours. After the reaction was completed, water (100 mL) was added, extracted with ethyl acetate (100 mL×3), the combined organic phase was concentrated under reduced pressure to remove the solvent, and the residue was passed through a silica gel column layer with a mixed solvent of petroleum ether and ethyl acetate as eluent. Analysis, separation and purification gave white solid I-a (2.010g, yield 90%); 1 HNMR (400MHz, CDCl 3 ): δ8.16(dd, J=7.8, 1.4Hz, 1H), 7.52-7.34(m, 6H), 7.32-7.21(m, 2H), 4.00(t, J=6.4Hz, 2H), 3.15( t, J = 6.4Hz, 2H); 13 C NMR (100MHz, CDCl 3 ): δ164.22, 143.11, 138.31, 132.06, 129.72, 128.94, 128.77, 127.22, 126.97, 126.27, 125.33, 49.43, 28.65.

Embodiment 2

[0027] Using the same method as in Example 1, sodium methoxide was used instead of potassium tert-butoxide to obtain white solid I-a (1.608 g, yield 72%).

Embodiment 3

[0029] Using the same method as in Example 1, using dimethyl sulfoxide instead of N,N-dimethylformamide as the solvent, a white solid I-a (1.786 g, yield 80%) was obtained.

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Abstract

The invention relates to a synthetic method of 3,4-dihydroisoquinolin-1-one and isoindolin-1-one derivatives; particularly, a base is added to 2-allyl-benzamide serving as a raw material under the protection of nitrogen, and heating is performed in a solvent to obtain dihydroisoquinolin-1-one or isoindolin-1-one compounds under high yield. The synthetic method is simple to perform, high in reaction yield and low in usage of bases in reaction, has no need for using transition metal catalysts, and is highly worthy of application in the industrial preparation of isoindolin-1-one compounds.

Description

technical field [0001] The invention relates to a new method for synthesizing 3,4-dihydroisoquinolin-1-one and isoindolin-1-one derivatives, which belongs to the field of organic synthesis. Background technique [0002] Dihydroisoquinolin-1-ones and isoindolin-1-ones are widely found in various natural products and drugs, such as the anti-anxiety drug Patinclone, the gastric motility drug palonosetron, a Losetron and the antithrombotic drug apixaban, etc. Dihydroisoquinolin-1-one and isoindoline-1-one compounds are also important precursors for the synthesis of tetrahydroisoquinoline, isoquinoline and isoindole compounds. [0003] At present, the methods for synthesizing dihydroisoquinolin-1-ones include: the oxidation of tetrahydroisoquinoline (Synlett, 2011, 1121); the intermolecular insertion reaction of transition metal catalyzed amides and alkenes (J.Am.Chem .Soc., 2011,133,6449); intramolecular Pay-Grass acylation of isocyanate compounds and carbamate compounds (Tetr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/24C07D401/04C07D209/46
CPCC07D209/46C07D217/24C07D401/04
Inventor 张学景陈振宇鄢明
Owner SUN YAT SEN UNIV
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