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1-aryl isoquinoline compound and synthetic method thereof

A technology for aryl isoquinolines and compounds, applied in the field of 1-aryl isoquinoline compounds and their synthesis, capable of solving problems such as limiting industrial applications and high costs

Active Publication Date: 2020-11-17
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such a high price severely limits downstream industrial applications

Method used

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  • 1-aryl isoquinoline compound and synthetic method thereof
  • 1-aryl isoquinoline compound and synthetic method thereof
  • 1-aryl isoquinoline compound and synthetic method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Using 2-naphthol 1a and isoquinoline 2a as substrates, the effect of acylating reagents was evaluated in the presence of excess isoquinoline in DCM at 0 °C, Boc 2 O as an acylating agent can only obtain the by-product of esterification of 2-naphthol, other acid chlorides and acid anhydrides, including TFAA, Ac 2 O, BzCl, MsCl, TsCl and pivaloyl chloride all failed to give the expected product. Traces of intermediate B were detected by LCMS when AcCl or benzyl chloroformate was used. Finally, it was 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 (0.5mmol) and 2a (1.25mmol) in CH 2 Cl 2 (4mL), stirred at 0°C for 0.5h, then added 1a (0.50mmol) of CH 2 Cl 2 ((4 mL) solution and stirred for an additional 2 hours.

[0069] Then study the reaction conditions that intermediate B is co...

Embodiment 2

[0088]

[0089] 3b was synthesized according to the general method, the yield was 86%, white solid, and the 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 )δ 158.2, 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, the yield was 84%, 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 )δ 157.5, 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 a structure shown as a general formula I. In the formula I, R1 and R2 are independentlyselected from hydrogen, alkyl, alkoxy, phenyl, halogen, an ester group, a cyano group, an aldehyde group, acyl, trifluoromethyl, alkenyl, alkynyl, amino, hydroxyl, carboxyl, nitro, acylamino, benzyl,methylphenyl, methoxyphenyl or halogenated phenyl; and R1 and R2 are not hydrogen at the same time. The invention also discloses a synthetic method of the 1-aryl isoquinoline compound. The method disclosed by the invention has excellent chemical selectivity, high atom economy and step economy, the raw materials are cheap and easy to obtain, the purification process is simple, large-scale synthesis can be realized, and the product can be derived to obtain chiral QUINAP.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates 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 skeletons of functional molecules, is an important research direction in synthetic chemistry. [0003] 1-(1-isoquinolyl)-2-naphthyl alcohol (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 tran...

Claims

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Application Information

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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