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Aryl heterocyclic derivative and synthesis method thereof

A synthesis method and derivative technology, applied in organic chemistry and other directions, can solve problems such as pollution, and achieve the effects of good reaction universality, mild reaction conditions and high reaction conversion rate.

Pending Publication Date: 2022-01-21
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the introduction of aryl groups on heterocyclic compounds often requires the pre-functionalization of substrates, and transition metals as catalysts cause potential contamination of target products.

Method used

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  • Aryl heterocyclic derivative and synthesis method thereof
  • Aryl heterocyclic derivative and synthesis method thereof
  • Aryl heterocyclic derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of compound (I-1)

[0033]

[0034] Add 0.1mmol of N-methylquinoxalinone, 0.15mmol of iodine ylide, 0.002mmol of eosin Y, and 0.1mmol of potassium carbonate to the reaction tube, dissolve in dimethyl sulfoxide solvent, and react under LED light at 25°C for 12 Hours, purified by column chromatography to obtain the target product (I-1), the separation yield was 89%.

[0035] Product NMR data: 1 H NMR (400MHz, CDCl 3 ): δ8.32-8.29(m, 2H), 7.92(dd, J=8.0Hz, J=1.2Hz, 1H), 7.54(t, J=7.9Hz, 1H), 7.47(t, J=3.3Hz ,3H),7.32(m,2H),3.74(s,3H); 13 CNMR (100MHz, CDCl 3 ): δ154.7, 154.1, 136.1, 133.4, 133.1, 130.5, 130.3, 130.3, 129.6, 128.1, 113.6, 29.3ppm.

[0036] High resolution mass spectrometry data: HRMS(ESI):m / z calcd for C 15 h 12 N 2 O[M+H] + , 237.1022. Found: m / z 237.1022.

Embodiment 2

[0038] Synthesis of compound (I-2)

[0039]

[0040] Add 0.1mmol of N-methylquinoxalinone, 0.15mmol of 4-methyliodoylide, 0.002mmol of eosin Y, and 0.1mmol of potassium carbonate to the reaction tube, dissolve in dimethyl sulfoxide solvent, 25°C, LED React under light for 12 hours, and purify by column chromatography to obtain the target product (I-2), with an isolated yield of 75%.

[0041] Product NMR data: 1 H NMR (400MHz, CDCl 3 ): δ8.24(d, J=8.2Hz, 2H), 7.93(dd, J=8.0Hz, J=1.3Hz, 1H), 7.55(td, J=7.5Hz, J=1.4Hz, 1H), 7.38-7.28(m,4H),3.77(s,3H),2.42(s,3H); 13 C NMR (100MHz, CDCl 3): δ154.8, 154.1, 140.6, 133.3, 133.3, 133.2, 130.4, 130.1, 129.5, 128.8, 123.7, 113.5ppm.

[0042] High resolution mass spectrometry data: HRMS(ESI):m / z calcd for C 16 h 14 N 2 O[M+H] + , 251.1179. Found: m / z 251.1180.

Embodiment 3

[0044] Synthesis of compound (I-3)

[0045]

[0046] Add 0.1 mmol of N-methylquinoxalinone, 0.15 mmol of 4-trifluoromethyl iodoylide, 0.002 mmol of eosin Y, and 0.1 mmol of potassium carbonate to the reaction tube, dissolve in dimethyl sulfoxide solvent, and keep at 25°C , reacted under LED light for 12 hours, purified by column chromatography to obtain the target product (I-3), and the separation yield was 67%.

[0047] Product NMR data: 1 H NMR (400MHz, CDCl 3 ): δ8.46(d, J=8.1Hz, 2H), 7.96(dd, J=8.0Hz, J=1.3Hz, 1H), 7.73(d, J=8.3Hz, 2H), 7.62(td, J =8.6Hz, J=1.4Hz, 1H), 7.43-7.36(m, 2H), 3.78(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ154.6, 152.6, 139.3, 133.5, 133.0, 131.8(d, J=32.1Hz), 130.9(d, J=32.5Hz), 129.9, 124.1(d, J=272.2Hz), 125.0(q, J= 3.7Hz), 124.0, 113.7, 29.4ppm; 19 F NMR (376MHz, CDCl 3 ): -62.80(s)ppm.

[0048] High resolution mass spectrometry data: HRMS(ESI):m / z calcd for C 16 h 11 f 3 N 2 O[M+H] + , 305.0896. Found: m / z 305.0894.

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Abstract

The invention discloses an aryl heterocyclic derivative and a synthesis method thereof, and the synthesis method comprises the following specific steps: taking a heterocyclic compound and an iodine ylide compound as raw materials, adding a catalyst, an additive and a solvent, and reacting under the illumination condition to obtain the aryl heterocyclic derivative as shown in the formula (I), the reaction process is shown in the formula (II), in the formula (II), R1 is hydrogen, halogen, C1-C5 alkyl or trifluoromethyl; R2 is hydrogen, halogen, C1-C5 alkyl or trifluoromethyl; R3 is hydrogen, halogen, C1-C5 alkyl or trifluoromethyl; M is a nitrogen-containing heterocyclic group or an oxygen-containing heterocyclic group, the structure of the nitrogen-containing heterocyclic group is shown as a formula (Het-a), (Het-b), (Het-c), (Het-d) or (Het-e), and the oxygen-containing heterocyclic group is shown as a formula (Het-f) or (Het-g). According to the synthesis method, raw materials are simple, easy to obtain and environmentally friendly. The aryl heterocyclic derivative has research value in the fields of medicine and organic synthesis.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, in particular to an aryl heterocyclic derivative and a synthesis method thereof Background technique [0002] Arylheterocyclic derivatives are an important class of organic synthesis intermediates, which have important application value in the fields of natural products, pharmaceutical production, and functional materials. However, the introduction of aryl groups on heterocyclic compounds often requires prefunctionalization of substrates, and transition metals as catalysts cause potential contamination of target products. Therefore, it is necessary to develop an environmentally friendly, green and efficient aryl acquisition method for the C–H arylation of heterocycles. Contents of the invention [0003] The object of the present invention is to provide an aryl heterocyclic derivative and a synthesis method thereof, and the provided aryl heterocyclic derivative has research value in th...

Claims

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Application Information

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IPC IPC(8): C07D241/44C07D241/20C07D237/12C07D241/42C07D311/16C07D493/04C07D311/36C07D241/18
CPCC07D241/44C07D241/20C07D237/12C07D241/42C07D311/16C07D493/04C07D311/36C07D241/18
Inventor 崔秀灵任杰皮超吴养洁
Owner ZHENGZHOU UNIV
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