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A kind of asymmetric synthesis method of trans-tetrahydrofuran/pyranotetrahydroquinoline derived chiral compound

A technology of tetrahydroquinoline and tetrahydrofuran, which is applied in the direction of organic chemistry, can solve the problems of synthesis difficulty, etc., and achieve the effect of simple operation, convenient synthesis method and mild reaction conditions

Active Publication Date: 2021-07-02
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are only a small number of reports on the synthesis of cis-tetrahydrofuran / pyrano-tetrahydroquinoline derivative chiral compounds based on Diels-Alder reaction and Povarov reaction; The construction of chiral compounds has not yet been realized, and there are certain difficulties and challenges in their synthesis; from the perspective of asymmetric catalytic design and biomedicine, this trans-tetrahydropyranotetrahydroquinoline derivative Chiral compounds have great development potential

Method used

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  • A kind of asymmetric synthesis method of trans-tetrahydrofuran/pyranotetrahydroquinoline derived chiral compound
  • A kind of asymmetric synthesis method of trans-tetrahydrofuran/pyranotetrahydroquinoline derived chiral compound
  • A kind of asymmetric synthesis method of trans-tetrahydrofuran/pyranotetrahydroquinoline derived chiral compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of trans-tetrahydropyranotetrahydroquinoline derivative chiral compounds shown in structural formula 3a

[0029] Compound (0.12mmol) and 2-amino-3,5-dibromo-benzaldehyde (0.1 mmol) and chiral phosphoric acid catalyst (0.01 mmol) as shown in structural formula 5a are added with magnetic Add 1.0mL of dichloromethane to a Kjeldahl flask after vacuuming and filling with nitrogen, then place the reaction system in an oil bath at 40°C for 24 hours, monitor with a TLC plate, after the reaction is complete, remove the solvent under reduced pressure, and separate by column chromatography (petroleum ether: ethyl acetate=15:1), that is, the trans-tetrahydropyranotetrahydroquinoline derivative chiral compound shown in structural formula 3a (white solid, 43.1mg, 98%, 98%ee ); The chemical reaction formula of this method is:

[0030]

[0031] The trans-tetrahydropyranotetrahydroquinoline derived chiral compound shown in structural formula 3a was respectively subjected t...

Embodiment 2

[0038] Synthesis of trans-tetrahydropyranotetrahydroquinoline derivative chiral compounds shown in structural formula 3b

[0039] Compound (0.12mmol) and 2-amino-3,5-dibromo-benzaldehyde (0.1mmol) as shown in structural formula 1b and chiral phosphoric acid catalyst (0.01mmol) as shown in structural formula 5a are added Add 1.0mL of dichloromethane to a Kjeldahl flask after vacuuming and filling with nitrogen, then place the reaction system in an oil bath at 40°C for 24 hours, monitor with a TLC plate, after the reaction is complete, remove the solvent under reduced pressure, and separate by column chromatography (petroleum ether: ethyl acetate = 15:1), that is, to obtain the trans-tetrahydropyranotetrahydroquinoline derivative chiral compound shown in structural formula 3b (white solid, 44.7mg, 98%, 98%ee ); The chemical reaction formula of this method is:

[0040]

[0041] The trans-tetrahydropyranotetrahydroquinoline derived chiral compound shown in structural formula 3...

Embodiment 3

[0048] Synthesis of trans-tetrahydropyranotetrahydroquinoline derivative chiral compounds shown in structural formula 3c

[0049] Compound (0.12mmol) and 2-amino-3,5-dibromo-benzaldehyde (0.1mmol) as shown in structural formula 1c and chiral phosphoric acid catalyst (0.01mmol) as shown in structural formula 5a are added Add 1.0mL of dichloromethane to a Kjeldahl flask after vacuuming and filling with nitrogen, then place the reaction system in an oil bath at 40°C for 24 hours, monitor with a TLC plate, after the reaction is complete, remove the solvent under reduced pressure, and separate by column chromatography (petroleum ether: ethyl acetate=15:1), that is, to obtain the trans-tetrahydropyranotetrahydroquinoline derivative chiral compound shown in structural formula 3c (white solid, 47.4mg, 98%, 98%ee ); The chemical reaction formula of this method is:

[0050]

[0051] The trans-tetrahydropyranotetrahydroquinoline derived chiral compound represented by structural formu...

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Abstract

The invention discloses an asymmetric synthesis method of chiral compounds derived from trans-tetrahydrofuran / pyranotetrahydroquinoline. The method uses 5-o-hydroxyphenyl-4-ene-1-pentanol derivatives and o- The aminobenzaldehyde derivative is reacted under the action of a chiral phosphoric acid catalyst to obtain a chiral compound derived from trans-tetrahydrofuran / pyranotetrahydroquinoline. The present invention provides an efficient, simple and convenient method for the first synthesis of trans-tetrahydrofuran / pyranotetrahydroquinoline derived chiral compounds by adopting dearomatization, Prins cyclization and aza-Michael addition series reaction modes resolve resolution. The method of the invention is simple to operate, and the reaction conditions are mild, and two new heterocycles, three new chemical bonds (C-O, C-C, C-N) and three adjacent quaternary carbon chirals are constructed in the one-pot reaction. A series of chiral compounds derived from trans-tetrahydrofuran / pyranotetrahydroquinoline were constructed.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to an asymmetric synthesis method of trans-tetrahydrofuran / pyranotetrahydroquinoline derived chiral compounds. Background technique [0002] Tetrahydroquinoline-derived chiral compounds and their derivatives are widely used in asymmetric catalysis, biomedicine, chemical dyes and other fields. How to synthesize optically pure tetrahydroquinoline-derived chiral compounds concisely and efficiently has attracted the attention of many chemists. There are only a small number of reports on the synthesis of cis-tetrahydrofuran / pyrano-tetrahydroquinoline derivative chiral compounds based on Diels-Alder reaction and Povarov reaction; The construction of chiral compounds has not yet been realized, and there are certain difficulties and challenges in their synthesis; from the perspective of asymmetric catalytic design and biomedicine, this trans-tetrahydropyranotetrahydroqui...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052C07D491/048
CPCC07D491/048C07D491/052
Inventor 周岭孙怀日陈洁
Owner NORTHWEST UNIV
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