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Method for synthesizing polysubstituted pyrido [1, 2-e] purine compound through electrochemical dehydrogenation coupling

A 2-e, multi-substitution technology, used in electrolytic components, electrolytic processes, electrolytic organic production, etc., which can solve the problems of safety, poor functional group compatibility, and low reaction efficiency.

Active Publication Date: 2021-09-14
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the existing problems in the prior art: 1) limited range of substrates, poor functional group compatibility, increased temperature, low reaction efficiency or potential safety issues

Method used

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  • Method for synthesizing polysubstituted pyrido [1, 2-e] purine compound through electrochemical dehydrogenation coupling
  • Method for synthesizing polysubstituted pyrido [1, 2-e] purine compound through electrochemical dehydrogenation coupling
  • Method for synthesizing polysubstituted pyrido [1, 2-e] purine compound through electrochemical dehydrogenation coupling

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Condition optimization experiment

[0024]

[0025]

[0026] a Standard conditions: substrate 1 (0.2mmol), KI (20mol%) in acetonitrile / acetic acid (3mL, v / v=5 / 1) solvent, two platinum electrodes (15×10×2mm 3 / piece), non-divided electrolytic cell, 27 ℃, 7mA (positive electrode 2.33mA / cm 2 ), 5.5h; b yield through 1 H NMR calculation (using CH 2 Br 2 as an internal standard); c The separation yields are in parentheses.

[0027] Finally determine the optimal conditions: compound 1 (0.20mmol), KI (20mol%), CH 3 CN:AcOH(2.5:0.5), 7mA was reacted at 27°C for 5.5h.

Embodiment 2

[0029]

[0030] In a non-divided electrolyzer, the substrate 1a (46.4mg, 0.20mmol) and KI (6.7mg, 0.04mmol, 20mol%) were dissolved in the mixed solvent CH 3 CN / HOAc (2.5 mL / 0.5 mL). Electrolysis was performed at 27 °C (oil bath temperature) using a constant current of 7.0 mA until the substrate was completely consumed (by TLC or 1 H NMR analysis monitoring). After the reaction, the solvent was removed under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (hexane / EtOAc: 5 / 1) to obtain colorless solid 2a (44.2 mg, yield 96%). 1 H NMR (600MHz, CD 2 Cl 2 ):8.46(d,J=7.2Hz,1H),7.57(d,J=9.6Hz,1H),7.25-7.13(m,1H),6.96-6.65(m,1H),4.00(s,3H) ,3.44(s,3H). 13 C NMR (150MHz, CD 2 Cl 2 ):159.5, 152.4, 144.5, 133.2, 126.7, 125.1, 121.4, 121.3, 115.0, 33.3, 30.0.

Embodiment 3

[0032]

[0033] With the above reaction conditions, starting from 1i (56.9mg, 0.2mmol), a white solid 2i (40.7mg, yield 72%) was obtained. 1 H NMR (600MHz, CDCl 3 ):8.18(d,J=7.2Hz,1H),7.61(d,J=9.6Hz,1H),7.24-7.13(m,1H),6.83(t,J=7.8Hz,1H),6.23-6.10 (m,1H),6.03-5.89(m,1H),5.37(d,J=10.8Hz,1H),5.29(d,J=16.8Hz,1H),5.26-5.15(m,2H),5.07( s,2H),4.74(d,J=6Hz,2H). 13 C NMR (150MHz, CDCl 3 ):157.7,150.6,143.3,131.8,131.8,131.2,125.6,124.0,120.2,120.2,118.0,117.7,113.9,46.3,44.2.

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Abstract

The invention discloses a method for synthesizing a polysubstituted pyrido [1, 2-e] purine compound through electrochemical dehydrogenation coupling, and belongs to the technical field of organic chemistry. In a non-separation electrolytic tank, N1, N3-disubstituted 5-(pyridine-2-amino) pyrimidine-2, 4-(1H, 3H)-diketone 1 is used as a raw material, in the presence of potassium iodide, a constant-current electrolytic reaction is carried out in an organic solvent, and a polysubstituted pyrido [1, 2-e] purine compound 2 is obtained. The method is mild in reaction condition, environment-friendly, high in yield and good in purity, a C-N bond cyclization product can be obtained with high selectivity, and a simple and effective synthesis way is provided for the polysubstituted pyrido [1, 2-e] purine compound.

Description

technical field [0001] The invention relates to a preparation method of polysubstituted pyrido[1,2-e]purine compounds, belonging to the field of organic chemistry. Background technique [0002] Polysubstituted pyrido[1,2-e]purines, especially chemically modified tricyclic or tetracyclic fused xanthines, are various adenosine receptor antagonists or phosphodiesterase inhibitors, and these derivatives Potential therapeutic applications have been shown in various diseases, including cancer, ischemic stroke, Parkinson's disease, Alzheimer's disease, schizophrenia, and asthma, among others. [0003] The research on the synthesis of polysubstituted pyrido[1,2-e]purines is not complete yet. In 2009, the literature reported a method for the synthesis of polysubstituted pyrido[1,2-e]purines by silver-catalyzed isomerization-hydroamination of terminal alkynes under microwave radiation (Adv.Synth.Catal., 2009, 351, 2770–2778). In 2013, the literature reported iron-catalyzed aerobic ...

Claims

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Application Information

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IPC IPC(8): C25B3/09C25B3/07C25B3/05C25B3/29
CPCC25B3/09C25B3/05C25B3/07C25B3/29
Inventor 杨启亮李艳艳刘颖渠桂荣郭海明
Owner HENAN NORMAL UNIV
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