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Preparation method for 4-aryl isoquinoline-1,3(2H,4H)-diketone compound

An aryl isoquinoline and diketone technology, applied in the field of drug synthesis, can solve the problems of poor selectivity, large fluctuation range of yield, difficult purification and the like

Active Publication Date: 2018-03-16
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The key step involved in most of the above methods is the ring-closing step, which involves the introduction and conversion of multi-step functional groups, which has poor selectivity, large fluctuation range of yield, low yield, limited product types, and many by-products. Deficiencies such as difficulty in purification

Method used

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  • Preparation method for 4-aryl isoquinoline-1,3(2H,4H)-diketone compound
  • Preparation method for 4-aryl isoquinoline-1,3(2H,4H)-diketone compound
  • Preparation method for 4-aryl isoquinoline-1,3(2H,4H)-diketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080]

[0081] Yield 95%.

[0082] 1 H NMR (500MHz, CDCl 3 )δ8.28(d, J=7.1Hz, 1H), 7.53(td, J=7.6, 1.3Hz, 1H), 7.46(t, J=7.3Hz, 1H), 7.34(d, J=6.5Hz, 2H),7.31–7.17(m,6H),7.15–7.05(m,3H),5.23(d,J=13.9Hz,1H),5.14–4.98(m,2H).

[0083] 13 C NMR (126MHz, CDCl 3 )δ171.77, 164.61, 138.89, 138.18, 136.87, 133.98, 129.04, 128.92, 128.71, 128.45, 128.33, 128.30, 127.98, 127.94, 127.41, 125.36, 52.65, 43.66.

[0084] HRMS(ESI):exact mass calculated for[M+H] + 328.1338, found 328.1335, melting point 81-82°C.

Embodiment 2

[0086]

[0087] Yield 92%.

[0088] 1 H NMR (400MHz, CDCl 3 )δ8.33–8.24(m,1H),7.59–7.43(m,2H),7.38–7.18(m,7H),7.06(dd,J=26.8,8.0Hz,3H),5.22(d,J= 13.8Hz, 1H), 5.05(d, J=15.2Hz, 2H).

[0089] 13 C NMR (101MHz, CDCl 3 )δ171.31, 164.35, 137.57, 137.29, 136.72, 134.08, 134.02, 129.85, 129.17, 129.05, 128.73, 128.36, 128.20, 127.50, 125.31, 51.86, 43.69.

[0090] HRMS(ESI):exact mass calculated for[M+H] + 362.0940, found 362.0939, melting point 88-89°C.

Embodiment 3

[0092]

[0093] Yield 95%.

[0094] 1 H NMR (400MHz, CDCl 3 )δ8.26(d,J=7.9Hz,1H),7.57–7.40(m,2H),7.35(d,J=6.5Hz,2H),7.28–7.16(m,3H),7.10(dd,J =12.9,7.8Hz,3H),6.98(d,J=8.0Hz,2H),5.22(d,J=13.9Hz,1H),5.04(d,J=13.6Hz,2H),2.30(s,3H ).

[0095] 13 C NMR (101MHz, CDCl 3 )δ 171.91, 164.62, 138.42, 137.74, 136.91, 135.99, 133.91, 129.70, 128.83, 128.73, 128.30, 128.27, 128.25, 127.85, 127.37, 125.27, 52.25, 413.02,

[0096] HRMS(ESI):exact mass calculated for[M+H] + 342.1487, found 342.1486, melting point 98-99°C.

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Abstract

The invention provides a preparation method for a 4-aryl isoquinoline-1,3(2H,4H)-diketone compound. The preparation method comprises the following steps: in a solvent, with imide as shown in a formula(II) which is described in the specification as a raw material, and in the presence of a palladium catalyst, a ligand and alkali, allowing the imide to react with substituted aromatic hydrocarbon asshown in a formula (III) which is described in the specification so as to generate the 4-aryl isoquinoline-1,3(2H,4H)-diketone compound as shown in a formula (I) which is described in the specification. The preparation method provided by the invention has the advantages of stable operation, high yield, low production cost, etc.; preparation of a target object can be completed by a one-step reaction; the operation is simple and convenient; the yield is high and generally reaches 90% to 99%; the use of an expensive and hazardous reagent is avoided; a synthetic method with large-scale preparationvalues is realized; conditions are stable; the yield is high; and a selection for a novel preparation method is provided for development and application of an isoquinoline diketone compound. The preparation method provided by the invention has a synthetic route as described in the specification.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of 4-arylisoquinoline-1,3(2H,4H)-dione compounds. Background technique [0002] Among the many heterocyclic compounds, isoquinolinedione and its derivatives have attracted widespread attention due to their remarkable pharmacological and biological activities, and their skeleton structures frequently appear in natural molecules and drug molecules, which can be used for analgesia and antitumor (such as anti-tumor activity of pancreatic cancer cells, cyclin-dependent kinase inhibitors, caspase inhibitors, anti-S180 tumor activity, etc.), HIV-I RT inhibitors, 5-HT3 receptor antagonists, etc., providing The preparation method of substituted isoquinolinediones has important practical and theoretical value. [0003] About the synthesis of isoquinoline diketones, following reports are arranged: [0004] Method 1. Reported in literature (Org.let., 2014, 16, 5...

Claims

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Application Information

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IPC IPC(8): C07D217/24C07D409/04
CPCC07D217/24C07D409/04
Inventor 杨元勇汤磊李应贤程铖杨果
Owner GUIZHOU MEDICAL UNIV
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