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Novel isatin derivative nitration method
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A derivative and a new method technology, applied in the field of nitration of isatin derivatives, can solve the problems of poor nitration selectivity, limited application of concentrated sulfuric acid, poor reaction effect, etc., achieve mild reaction conditions and expand the scope of application
Inactive Publication Date: 2021-03-30
CHANGZHOU UNIV
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[0005] Due to the use of sulfuric acid with very high acidity and oxidizing properties as catalyst and solvent in this type of method, although the reaction speed is fast and the cost is low, there are still problems such as poor nitration selectivity and many side reactions (such as sulfonation), especially for those containing The raw material of the reducing group, the reaction effect is poor, such as sulfuric acid is easy to add reaction to the unsaturated bond to generate the corresponding ester
These all limit the application of concentrated sulfuric acid in the nitration of complex molecules
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Embodiment 1
[0024] At room temperature, 16.1mg and 25.5mg of silver nitrate were added to 1mL of trifluoroacetic acid, heated to 60°C, reacted at this temperature for 30 minutes, the trifluoroacetic acid was removed, and the residue was separated by column chromatography to obtain compound 2a, whose molecular structure was: It was a red solid, 87% yield. 1 H NMR (300MHz, DMSO-d 6 ): δ8.56-8.53(dd, J=2.4Hz, J=8.7Hz, 1H), 8.24-8.23(d, J=3.0Hz, 1H), 7.37-7.34(d, J=9.0Hz, 1H) ,3.22(s,3H); 13 C NMR (75MHz, DMSO-d 6 ): δ181.3, 158.9, 155.7, 142.9, 133.0, 119.0, 117.8, 110.9, 26.5ppm. HRMS (ESI): C 9 h 6 N 2 NaO 4 [M+Na] + The theoretical value is 229.0220, and the measured value is 229.0164.
Embodiment 2
[0027] by As raw material, prepare compound 2b, its molecular structure is: It was a red solid, 29% yield. 1 H NMR (400MHz, DMSO-d 6 ):δ9.51(s,1H),8.44-8.42(dd,J=1.0Hz,J=8.5Hz,1H),8.00-7.98(d,J=7.3Hz,1H),7.36-7.32(dd, J=7.5Hz, J=8.4Hz, 1H).; 13 C NMR (100MHz, DMSO-d 6 ): δ181.5, 159.9, 145.2, 131.9, 131.4, 130.5, 122.5, 121.4ppm. HRMS (ESI): C 8 h 4 N 2 NaO 4 [M+Na] + The theoretical value is 215.0069, and the measured value is 215.0036.
Embodiment 3
[0029] by As raw material, prepare compound 2c, its molecular structure is: It was a red solid, 72% yield. 1 H NMR (400MHz, DMSO-d 6 ):δ7.86-7.86(d,J=2.1Hz,1H),7.73-7.73(d,J=2.1Hz,1H),3.32(s,3H). 13 C NMR (100MHz, DMSO-d 6 ): δ179.4, 158.0, 144.0, 142.2, 125.6, 122.1, 121.3, 121.2, 119.1, 30.2ppm.HRMS(ESI)C 10 h 4 f 3 N 2 o 5 [M-H] - : The theoretical value is 289.0073, and the measured value is 289.0093.
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Abstract
The invention belongs to the technical field of chemical pharmacy and fine chemicalengineering preparation, and particularly discloses a novel isatin derivative nitration method. Trifluoroacetic acidis adopted to replace traditional sulfuric acid, so that a nitro group can be efficiently introduced to the fifth position or the seventh position of the isatin derivative under the action of nitrate. The invention provides a practical synthesis method for preparing the nitro isatin compound, and the method is widely applied to the technical field of chemical pharmacy and fine chemicalengineering preparation.
Description
technical field [0001] The invention belongs to the technical field of chemical pharmacy and fine chemical preparation, and specifically discloses a new method for nitration of isatin derivatives. Background technique [0002] Isatin derivatives are important synthetic intermediates and are widely used to synthesize molecules with anti-tumor, anti-virus and anti-tuberculosis biological activities (Bioorg.Med.Chem.Lett.2006,16,2158–2162.DOI:10.1016 / j.bmcl.2006.01.063; Bioorg.Med.Chem.Lett.2006, 16, 2109–2112. DOI: 10.1016 / j.bmcl.2006.01.066; Bioorg.Med.Chem.Lett.2005, 15, 4451– 4455. DOI: 10.1016 / j.bmcl.2005.07.046). [0003] Aromatic nitration reaction is widely used in modern chemical industry. The development of the nitration reaction of isatin derivatives has important theoretical significance and practical value. The nitration reaction of isatin derivatives in the current literature mainly uses nitrate or nitric acid as the source of nitro, and generally uses sulfuri...
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