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Method for preparing 2-amino-1,2-dihydro-isoquinoline compound

A technology of dihydroisoquinoline and compounds, applied in the direction of organic chemistry, can solve the problems of long synthetic route, low overall yield, and limited range of substrates, and achieve low cost, mild conditions, and easy separation The effect of purification

Inactive Publication Date: 2010-07-28
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods are usually due to the long synthetic routes involved, the overall yield is not high, and the scope of substrates is limited

Method used

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  • Method for preparing 2-amino-1,2-dihydro-isoquinoline compound
  • Method for preparing 2-amino-1,2-dihydro-isoquinoline compound
  • Method for preparing 2-amino-1,2-dihydro-isoquinoline compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018]

[0019] methyl

[0020] 3-(2-(4-methylphenylsulfonamido)-3-phenyl-1, 2-dihydroisoquinolin-1-yl)-3-phenylpropanoate (3a)

[0021] After dissolving o-phenylynyl benzylhydrazone (2mmol) and cinnamaldehyde (2.2mol%) in the mixed solvent THF / MeOH (20mL, v / v, 9:1), silver trifluoromethanesulfonate (5mol%) was added successively %) and nitrogen heterocyclic carbene catalyst (5mol%), cesium carbonate (25mol%), reacted for 12 hours at 50° C. under nitrogen protection, and TLC detected that the raw materials disappeared completely, and the reaction was completed. During the post-treatment, the solvent was first spin-dried, quenched with water, extracted with ethyl acetate, anhydrous MgSO 4 After drying, the solvent was evaporated to dryness under reduced pressure, and the pure product 2-amino-1,2-dihydroisoquinoline compound 3a was separated by silica gel column chromatography. Yield: 90%.

[0022] Yield: 94%; 1 H NMR (400MHz, CDCl3) 1H NMR (400MHz, CDCl3): 7.41-7.27 (m, ...

Embodiment 2

[0024]

[0025] methyl

[0026] 3-(4-bromophenyl)-3-(2-(4-methylphenylsulfonamido)-3-phenyl-1,2-dihydroisoquinolin-1-yl) propanoate (3b)

[0027] After dissolving o-phenylynylbenzylhydrazone (2.0mmol) and p-bromocinnamaldehyde (2.2mol%) in a mixed solvent THF / MeOH (20mL, v / v, 9:1), add trifluoromethanesulfonic acid in sequence Silver (5mol%), nitrogen heterocyclic carbene catalyst (5mol%), and potassium carbonate (25mol%) were reacted at 50° C. for 12 hours under nitrogen protection. TLC detected that the raw materials disappeared completely, and the reaction was completed. During the post-treatment, the solvent was first spin-dried, quenched with water, extracted with ethyl acetate, anhydrous MgSO 4 After drying, the solvent was evaporated to dryness under reduced pressure, and the pure product 2-amino-1,2-dihydroisoquinoline compound 3b was separated by silica gel column chromatography. Yield 78%.

[0028] 1 H NMR (400MHz, CDCl 3): δ7.51-7.47(m, 2H), 7.36-7.29(m, 2H)...

Embodiment 3

[0030]

[0031] methyl 3-(4-bromophenyl)-3-(3-(4-chlorophenyl)-2-(4-methylphenylsu-lfonamido)-1,2-dihydroisoquinolin-1-yl)propanoate(3c)

[0032] After dissolving o-4'-chlorophenylethynyl benzylhydrazone (2.0mmol) and p-bromocinnamaldehyde (2.2mol%) in the mixed solvent THF / MeOH (20mL, v / v, 9:1), add in sequence Silver triflate (5mol%), nitrogen heterocyclic carbene catalyst (5mol%), and cesium carbonate (25mol%) were reacted at 50° C. for 12 hours under nitrogen protection. TLC detected that the raw materials disappeared completely, and the reaction was completed. During the post-treatment, the solvent was first spin-dried, quenched with water, extracted with ethyl acetate, anhydrous MgSO 4 After drying, the solvent was evaporated to dryness under reduced pressure, and the pure product 2-amino-1,2-dihydroisoquinoline compound 3c was separated by silica gel column chromatography. Yield 82%.

[0033] 1 H NMR (400MHz, CDCl 3 ): δ7.51-7.47(m, 2H), 7.36-7.29(m, 2H), 7.22-7....

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Abstract

The invention belongs to the technical field of organic chemistry, in particular to a method for preparing a 2-amino-1,2-dihydro-isoquinoline compound. The structure of the compound is characterized and confirmed by methods including 1H-NMR, 13C-NMR, HRMS, single-crystal X diffraction, and the like. The method comprises the following steps of: under the catalytic condition of silver triflate and N-heterocyclic carbene, carrying out one kettle method of series intramolecular cyclization and polarity reversal addition reaction on o-alkynyl phenyl hydrazone and alpha, beta-unsaturated aldehyde in tetrahydrofuran, methanol and alkali to efficiently prepare the 2-amino-1,2-dihydro-isoquinoline compound- a. The method has the advantages of high reaction efficiency, mild conditions, simple operation, lower cost, high product purity, convenient separation and purification and is suitable for large-scale preparation. The skeleton structure of the product has wide spectrum biological activity, and the compound has wide application prospect in discovery of new drugs.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of 2-amino-1,2-dihydroisoquinoline compound. Background technique [0002] Isoquinolines and 1,2-dihydroisoquinolines are important alkaloids with very important physiological activities, and they are also widely used in medicine, pesticides and other fields. Isoquinoline skeletons also widely exist in a variety of natural products. Therefore, the synthesis of isoquinoline derivatives has received widespread attention. The commonly used methods for synthesizing 1-substituted-1,2-dihydroisoquinolines reported in the literature are mainly based on two approaches. One is to obtain the isoquinoline skeleton through an intramolecular ring-closing reaction, such as the Bischler-Napieralski method, the Pictet-Grams method, the Pictet-Spengler method, and the Pomeranz-Fritish method. The other one uses isoquinoline as a starting material to o...

Claims

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Application Information

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IPC IPC(8): C07D217/18
Inventor 陈知远吴劼
Owner FUDAN UNIV
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