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Preparation method of fused ring compound containing indole skeleton

A compound and skeleton technology, applied in the field of preparation of fused ring compounds, can solve problems such as limited construction methods, cumbersome operations, and narrow substrate applicability, and achieve the effects of wide substrate applicability, simple system, and easy operation

Active Publication Date: 2021-06-25
UNIV OF SCI & TECH OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, in the prior art, the construction method of this type of fused ring compound containing indole skeleton is relatively limited, and most of the synthetic methods reported at present are prepared by utilizing 1,3-cyclohexanedione and phenylhydrazine through a multi-step reaction (De Candia , M., Zaetta, G., Denora, N., Tricarico, D.; Majellaro, M.; Cellamare, S.; Altomare, C.D. Eur. J. Med. Chem. 2017, 125, 288-298.), cumbersome to operate , the product loss is high, and the substrate applicability is also narrow, which limits the diverse synthesis of fused ring compounds containing indole skeletons

Method used

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  • Preparation method of fused ring compound containing indole skeleton
  • Preparation method of fused ring compound containing indole skeleton
  • Preparation method of fused ring compound containing indole skeleton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Preparation of 5-methyl-7-phenyl-5,6,7,12-tetrahydro-14H-7,13-methylbenzo[7,8]azo[4,3-b] Indol-14-one (2a)

[0044]

[0045] Put a rotor into a 10mL dry Schlenk tube, weigh 0.2mmol of raw material 1a (1.0eq), 0.02mmol of palladium iodide (10mol%), 0.6mmol of cesium carbonate (3eq) and 0.04mmol of 4-(dimethylamino ) triphenylphosphine (20mol%) was placed in the bottle; under argon atmosphere, add ultra-dry acetonitrile / toluene (1:1, 2mL) and 1.4mmol H 2 O (7.0 equivalents), the mixture was pre-stirred at room temperature for 30min, and the reaction mixture was placed in a 100°C oil bath and stirred for 12h; after the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate, filtered with diatomaceous earth, and the filtrate was vacuum Concentration gave a yellow oily liquid; the obtained crude product was separated by flash column chromatography (silica gel soaked in triethylamine, petroleum ether / ethyl acetate=4:1, v / v) to obtain t...

Embodiment 2

[0047] Example 2: Preparation of 5-methyl-7-(naphthalene-2-yl)-5,6,7,12-tetrahydro-14H-7,13-methylbenzo[7,8]azo[4 ,3-b]indol-14-one (2b)

[0048]

[0049] 1b was used as the starting substrate for the reaction to prepare the target product 2b, the reaction temperature was 100°C, and the reaction was carried out for 12 hours. The preparation method was basically the same as that in Example 1.

[0050] Product yield 78%; white solid; 1 H NMR (400MHz, CDCl 3 )δ8.09–8.00(m,1H),7.84–7.72(m,4H),7.54–7.42(m,2H),7.36–7.30(m,1H),7.28–7.14(m,7H),5.54( dd,J=16.1,2.0Hz,1H),4.51(d,J=16.1Hz,1H),4.28(dd,J=14.3,2.1Hz,1H),4.18(d,J=17.2Hz,1H), 3.89(s,3H),3.56(d,J=14.4Hz,1H),3.51(d,J=17.2Hz,1H). 13 C NMR (101MHz, CDCl 3 )δ169.05,143.88,143.39,140.31,137.23,135.65,133.10,132.18,129.77,128.64,128.04,127.62,127.50,127.23,127.16,127.00,126.66,126.39,125.67,125.34,122.57,121.74,121.05,109.60,109.41 ,57.82,49.54,49.13,38.82,30.21.HRMS(ESI)m / z calculated for C 30 h 25 N 2 O for[M+H] + :429...

Embodiment 3

[0051] Example 3: Preparation of 5-methyl-7-(4-methoxyphenyl)-5,6,7,12-tetrahydro-14H-7,13-methylbenzo[7,8]azo [4,3-b]indol-14-one (2c)

[0052]

[0053] 1c was used as the starting substrate of the reaction to prepare the target product 2c, the reaction temperature was 100°C, and the reaction was carried out for 12 hours. The preparation method was basically the same as that in Example 1.

[0054] Product yield 76%; white solid; 1 H NMR (400MHz, CDCl 3)δ8.06–7.99(m,1H),7.34–7.29(m,1H),7.27–7.21(m,4H),7.20–7.12(m,4H),6.90–6.80(m,2H),5.50( dd,J=16.1,2.0Hz,1H),4.47(d,J=16.1Hz,1H),4.21(dd,J=14.2,2.1Hz,1H),4.03(d,J=17.3Hz,1H), 3.84(s,3H),3.79(s,3H),3.46(d,J=17.2Hz,1H),3.44(d,J=14.0Hz,1H). 13 C NMR (101MHz, CDCl 3 )δ168.96,158.41,143.78,140.42,138.84,137.23,135.63,129.69,128.19,127.39,127.16,127.01,122.54,121.72,121.05,114.04,109.59,109.37,58.13,55.44,49.09,48.91,39.17,30.15.HRMS (ESI)m / z calculated for C 27 h 25 N 2 o 2 for[M+H] + :409.1916,found:409.1913.

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Abstract

The invention discloses a preparation method of a fused ring compound containing an indole skeleton. The preparation method comprises the following steps: carrying out intramolecular Heck reaction under the action of a palladium catalyst, a ligand, an additive and alkali carbonate, and further carrying out cascade reaction by using a sigma-alkyl palladium (II) intermediate generated in situ to obtain the fused ring compound containing the indole skeleton. The one-step method is adopted, construction of a complex fused ring structure is achieved through palladium catalysis, operation is easy, the complex fused ring compound containing the indole skeleton can be obtained without additional treatment, the substrate applicability is wide, the compound can tolerate multiple functional groups, and the product yield is good. An effective means is provided for synthesizing the fused ring compound containing the indole skeleton, and the method has economic practicability and industrial development prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a condensed ring compound containing an indole skeleton. Background technique [0002] Nitrogen-containing fused heterocyclic compounds refer to polycyclic organic compounds fused together by nitrogen-containing heterocyclic rings and benzene rings or heterocyclic rings. This type of compound has special physical and chemical properties of low toxicity and high systemic absorption and unique biological properties. Activity and other characteristics, can be used as intermediates of drug molecules, pesticides and materials. On the other hand, nitrogen-containing fused heterocyclic compounds can also easily introduce various functional groups to modify the chemical structure, and are widely used in the fields of total synthesis of natural products and research and development of new drug molecules. [0003] The fused ring compound conta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/18C07D495/22
CPCC07D471/18C07D495/22
Inventor 徐允河李曼
Owner UNIV OF SCI & TECH OF CHINA
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