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A method for synthesizing natural product clausenine
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A natural product, p-methoxyaniline technology, applied in the direction of organic chemistry, can solve cumbersome problems and achieve the effect of simple operation, high yield and convenient synthesis
Active Publication Date: 2016-01-27
CHANGZHOU XIAOGUO INFORMATION SERVICES
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[0011] Method (1) requires more steps to obtain the target product, which is cumbersome
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Embodiment 1
[0030] Example 1: Under the condition of oxygenatmosphere, p-methoxyaniline (2g), 6-diazo-3-methyl-2-cyclohexen-1-one (2.2g), copper acetate were added to the sealed tube (0.65g) and 1,4-dioxane (50mL); the reaction system was heated to 80 degrees Celsius for 3 hours under airtight conditions. The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2-(4-methoxyanilino)-5-methylphenol (3.1 g, yield: 83%); 1 HNMR (400MHz, CDCl 3 )δ6.98(d,J=7.6Hz,1H),6.79(d,J=8.4Hz,3H),6.70(d,J=7.6Hz,3H),5.86(s,1H),4.92(s, 1H),3.75(s,3H),2.31(s,3H); 13 CNMR (100MHz, CDCl 3 )δ154.0, 150.9, 139.5, 135.9, 127.6, 124.3, 121.6, 117.6, 115.8, 114.8, 55.7, 21.2
Embodiment 2
[0031] Example 2: Under the condition of oxygenatmosphere, p-methoxyaniline (2g), 6-diazo-3-methyl-2-cyclohexen-1-one (6.6g), copper acetate were added to the sealed tube (0.016g) and 1,4-dioxane (50mL); the reaction system was heated to 80 degrees Celsius for 3 hours under airtight conditions. The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2-(4-methoxyanilino)-5-methylphenol (3.4 g, yield: 91%); 1 HNMR (400MHz, CDCl 3 )δ6.98(d,J=7.6Hz,1H),6.79(d,J=8.4Hz,3H),6.70(d,J=7.6Hz,3H),5.86(s,1H),4.92(s, 1H),3.75(s,3H),2.31(s,3H); 13 CNMR (100MHz, CDCl 3 )δ154.0, 150.9, 139.5, 135.9, 127.6, 124.3, 121.6, 117.6, 115.8, 114.8, 55.7, 21.2
[0032] Step Ⅱ: Synthesis of N-(2-methoxy-4-methylphenyl)-p-methoxyaniline (literature method)
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Abstract
The invention discloses a method of synthesizing a natural product Clausenine and belongs to the field of organic synthesis. The method comprises the steps of reacting 6-diazo-3-methyl-2-cyclohexene-1-ketone with anisidine under the catalysis action of copper to generate 2-(4-methoxyphenyl amino)-5-methyl phenol, and then carrying out methylation and Pd-catalyzed C-C bond coupling to prepare the natural product, namely (b) Clausenine ( / b). The method has the advantages of few steps, simple operation and high yield.
Description
technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing natural product Clausenine. Background technique [0002] Clausenine is a carbazole natural product with antibacterial activity. Its structure is as follows: [0003] [0004] The synthetic method of this product that has been reported has following: [0005] (1) Synthesis 2007, No. 13, 1943–1948 [0006] [0007] (2)a: J. Org. Chem., 2008, 73(13), 5022–5028 [0008] b: Tetrahedron68 (2012) 6727e6736 [0009] [0010] Of the above two methods: [0011] Method (1) requires more steps to obtain the target product, which is cumbersome [0012] Method (2) requires the use of expensive phosphine ligands for the synthesis of intermediates. Contents of the invention [0013] The invention provides a method of using copper to catalyze the reaction of 6-diazo-3-methyl-2-cyclohexen-1-one and p-methoxyaniline to generate 2-(4-methoxyaniline)-5- m...
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