The Study On The Copper-catalyzed Synthesis Of 3-substituted Indole Derivatives In Water

Indole and its derivatives are important chemical raw materials, widely used in medicine, pesticides, perfumes, dyes, food and feed additives. Including in particular a 3-substituted indole derivatives which is a lot of natural products and biologically active compounds constitute an important framework, and therefore synthesis of compounds of this type has been one of the hot areas of organic synthesis.In recent years, with the development of green chemistry, water phase organometallic chemistry has made great breakthroughs in many organic reactions in water in the reaction medium to achieve. In order to further the establishment of ecological, green, environmentally friendly synthetic methods indoles, the paper carried a copper-catalyzed aqueous phase 3-substituted indole synthesis work. The specific contents are as follows:The first part explores included water in the use of Salicylaldehyde imine-Cu(II)complexes catalyzing to synthesis of 3-substituted indoles. Reference literature methods, we synthesized five Salicylaldehyde imine-Cu(II). Kind of catalyst in water can be smoothly catalytic indole and β- nitrostyrene Michael addition reaction. The reaction conditions are mild green. In water at room temperature the reaction can work, and the reaction substrates broad adaptability and high catalytic efficiency. Finally we synthesized 25 kinds of indole-3-substituted substrates, for 10 hours to obtain a yield of 80%-97%. And the successful implementation of the gram-scale amplification; while circulating catalyst used four times in the future still be able to obtain the compound substrate 87% yield.The second part explores included 2-pyrrole imide-Cu(II) complexes catalyzing to synthesis the three components reaction of the indole, malononitrile and aldehyde in the water phase,. First we synthesized four kinds of 2-pyrrole imide-Cu(II) complexes. Under the optimal reaction conditions [water, rt, Cat 7(5 mol %), 10 h], the separation of the model reaction yield reached 96%, meanwhile to other substrates instead of indole and aromatic aldehyde aldehyde. we got 16 kinds of target product yield being 70%-96%. Contrast to other methods, the literature has no alkaline, imild reaction condition, less catalyst.The third part was on the basis of the research content and further studyed 2-pyrrole imide-Cu(II) complexes catalyzing to synthesis the three components reaction of the indole, aniline and aldehyde. Under the optimal reaction conditions [water, rt, Cat 6(2 mol %), 12 h], the yield reached 93%, meanwhile extend to other substrates instead of indole and aldehyde, amine. 68%-95% of the yield of about 10 kinds of target products. Also, the method with other methods, the literature has a synthesis method is simple, does not need to be alkaline, mild reaction condition, catalyst dosage of the advantages of less.