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A kind of synthetic method of 5-oxo-2h-aryl[g]indole-1-oxide
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A synthesis method and oxide technology, applied in organic chemistry and other directions, can solve problems such as practical limitations, harsh reaction conditions, and serious environmental pollution of waste.
Active Publication Date: 2021-09-10
HENAN NORMAL UNIV
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Although these methods can effectively synthesize benzindole-1-oxides, there are still some problems that need to be solved urgently, such as: harsh reaction conditions, serious environmental pollution by waste, low oxidation selectivity, and the use of metal catalysts, etc. These deficiencies also make the practicability of the above method greatly limited.
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Embodiment 1
[0022]
[0023] 1a (0.5mmol, 122mg), 3a (volume fraction 95%, 10mmol, 614μL) and 2 (1mmol, 119μL) were sequentially added into the reaction tube, and the reaction was stirred at room temperature under air atmosphere for 3h. Then, the system was cooled to 0°C, and when a large amount of yellow solid precipitated, it was filtered with suction, washed with EtOH (volume fraction 95%, 500 μL), and dried to obtain product 4a (131 mg, 82%). The characterization data of this compound are as follows: mp: 104-105°C. 1 H NMR (600MHz, CDCl 3 )δ: 1.24(t, J=7.2Hz, 3H), 3.40-3.47(m, 2H), 3.53(dd, J 1 =18.6Hz,J 2 =1.8Hz,1H),3.70-3.75(m,1H),6.38(s,1H),7.25-7.30(m,3H),7.37-7.38(m,2H),7.56-7.63(m,2H), 8.20(dd,J 1 =7.2Hz,J 2 =1.2Hz,1H),9.12(d,J=7.2Hz,1H). 13 C NMR (150MHz, CDCl 3 )δ: 15.1, 37.3, 60.9, 106.8, 120.6, 124.9, 125.3, 125.6, 127.2, 128.8, 129.4, 130.9, 131.4, 133.1, 136.9, 138.1, 146.8, 183.4. HRMS calcd for C 20 h 16 NO 3 :318.1136[M-H] - ,found: 318.1143.
Embodiment 2
[0025] 1a (0.5mmol, 122mg), 3a (volume fraction 95%, 5mmol, 308μL) and 2 (1mmol, 119μL) were sequentially added into the reaction tube, and the reaction was stirred at room temperature under an air atmosphere for 3h. Then, the system was cooled to 0°C, and when a large amount of yellow solid precipitated, it was filtered with suction, washed with EtOH (volume fraction 95%, 500 μL), and dried to obtain product 4a (121 mg, 76%).
Embodiment 3
[0027] 1a (0.5mmol, 122mg), 3a (volume fraction 95%, 100mmol, 6.14mL) and 2 (1mmol, 119μL) were sequentially added into the reaction tube, and the reaction was stirred at room temperature under air atmosphere for 3h. Then, the system was cooled to 0°C, and when a large amount of yellow solid precipitated, it was filtered with suction, washed with EtOH (volume fraction 95%, 500 μL), and dried to obtain product 4a (123 mg, 77%).
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Abstract
The invention discloses a synthesis method of 5-oxo-2H-aryl[g]indole-1-oxide, which belongs to the technical field of organic synthesis. The key points of the technical scheme of the present invention are: the present invention directly synthesizes 5-oxo-2H ‑Aromatic ring [g]indole‑1‑oxide, the whole process is simple and efficient; the synthesis process can be carried out smoothly without using any metal catalyst or solvent, and the post-reaction treatment does not require column chromatography separation, It is economical, green, and environmentally friendly; the atom economy of the reaction is high, which meets the requirements of green chemistry; the substrate has a wide range of applications.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a synthesis method of 5-oxo-2H-aryl[g]indole-1-oxide. Background technique [0002] Benzindole-1-oxide widely exists in natural alkaloids, such as stephacidin B and wakialoid A, which have important biological activities in the treatment of breast cancer and anti-infection. At present, the synthesis methods of this kind of compounds mainly include: 1) the oxidation of benzindole; 2) the intramolecular reductive condensation reaction of 1-(2-nitrophenyl)-2-one catalyzed by zinc, etc. Although these methods can effectively synthesize benzindole-1-oxides, there are still some problems that need to be solved urgently, such as: harsh reaction conditions, serious environmental pollution by waste, low oxidation selectivity, and the use of metal catalysts, etc. These deficiencies also greatly limit the practicability of the above-mentioned method. In view of this, ...
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