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1-Aryl isoquinoline compound and its synthesis method

A technology of aryl isoquinoline and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of limited industrial application and high cost, and achieve the effects of unaffected yield, obvious cost advantage and simple purification process

Active Publication Date: 2022-07-05
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Such a high price severely limits downstream industrial applications

Method used

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  • 1-Aryl isoquinoline compound and its synthesis method
  • 1-Aryl isoquinoline compound and its synthesis method
  • 1-Aryl isoquinoline compound and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Using 2-naphthol 1a and isoquinoline 2a as substrates to evaluate the effect of acylating reagents, in the presence of excess isoquinoline, in DCM as solvent, at 0 °C, Boc 2 As an acylating reagent, O can only obtain the esterification by-product of 2-naphthol, other acid chlorides and acid anhydrides, including TFAA, Ac 2 None of O, BzCl, MsCl, TsCl and pivaloyl chloride gave the expected product. Traces of Intermediate B were detected by LCMS when AcCl or benzyl chloroformate was used. It was finally found that trifluoromethanesulfonyl chloride gave intermediate B in 40% isolated yield, and trifluoromethanesulfonic anhydride (Tf 2 O), intermediate B was obtained in 81% yield.

[0067]

[0068] Reaction conditions: acylating agent (0.5 mmol) and 2a (1.25 mmol) in CH 2 Cl 2 (4 mL), stirred at 0°C for 0.5 h, then added 1a (0.50 mmol) of CH 2 Cl 2 (4 mL) solution and stirred for an additional 2 hours.

[0069] Then, the reaction conditions for the conversion of ...

Embodiment 2

[0088]

[0089] 3b was synthesized according to the general method in 86% yield, white solid, characterization data:

[0090] 1 H NMR (400MHz, DMSO-d 6 )δ9.70(s,1H),8.67(d,J=5.7Hz,1H),8.03(d,J=8.2Hz,1H),7.90-7.87(m,2H),7.78(d,J=8.3 Hz,1H),7.74-7.70(m,1H),7.46-7.45(m,2H),7.31(d,J=8.8Hz,1H),7.10(dd,J=8.3,1.6Hz,1H),6.64 (s, 1H), 2.14 (s, 3H).

[0091] 13 C NMR (100MHz, DMSO-d 6 )δ158.2,152.9,142.6,135.9,135.6,134.1,130.3,129.5,128.1,128.0,127.4,127.0,127.0,126.2,124.9,122.8,112.0,118.0,117.3,21.6.

[0092] HRMS(ESI) accurate mass calculation [M+H] + C 20 H 16 NO + , m / z: 286.1226, measured value: 286.1225.

Embodiment 3

[0094]

[0095] 3c was synthesized according to the general method in 84% yield, white solid, characterization data:

[0096] 1 H NMR (400MHz, CDCl 3 )δ8.62(d,J=5.7Hz,1H),7.92(d,J=8.3Hz,1H),7.76-7.73(m,2H),7.72-7.68(m,1H),7.61-7.58(m , 2H), 7.41-7.37(m, 1H), 7.22(d, J=8.9Hz, 1H), 7.07-7.00(m, 2H), 2.45(s, 3H).

[0097] 13 C NMR (100MHz, CDCl 3 )δ157.5,152.7,141.8,137.1,132.7,131.1,130.7,130.4,129.0,128.6,128.3,128.2,127.3,127.2,127.1,124.9,120.8,119.0,117.1,21.3.

[0098] HRMS(ESI) accurate mass calculation [M+H] + C 20 H 16 NO + , m / z: 286.1226, measured value: 286.1225.

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Abstract

The invention belongs to the field of organic synthesis, and discloses a 1-aryl isoquinoline compound, which has the structure of general formula I: wherein, R 1 , R 2 each independently selected from hydrogen, alkyl, alkoxy, phenyl, halogen, ester, cyano, aldehyde, acyl, trifluoromethyl, alkenyl, alkynyl, amino, hydroxyl, carboxyl, nitro, amide, benzyl, methylphenyl, methoxyphenyl or halophenyl; and R 1 , R 2 Not both hydrogen. The invention also discloses a method for synthesizing the 1-aryl isoquinoline compound. The method of the invention has excellent chemical selectivity, high atom economy and step economy, cheap and easily available raw materials, simple purification process, large-scale synthesis, and the product can be derived to obtain chiral QUINAP.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a 1-arylisoquinoline compound and a synthesis method thereof. Background technique [0002] Biaryl skeletons are ubiquitous in organic catalysts, ligands and functional materials. How to quickly and efficiently construct biaryl skeletons, especially to obtain the core skeleton of functional molecules, is an important research direction in synthetic chemistry. [0003] 1-(1-Isoquinolinyl)-2-naphthol (QUINOL) is a representative atropisomeric biheteroaryl, which has been used as an N-O chelating ligand in cyclic ester polymerization, and can also be used For the synthesis of other ligands such as QUINAP, QUINOX and IAN. [0004] In addition, novel organic dyes derived from QUINOL stain vesicles in confocal fluorescence microscopy images. [0005] [0006] However, the synthesis of QUINOL and its derivatives still faces many challenges. The traditional transition metal-catalyz...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/20
CPCC07D217/20
Inventor 谭斌李绍玉向少华
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA