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The Research Of Multicomponent Reactions

Posted on:2012-10-02Degree:MasterType:Thesis
Country:ChinaCandidate:H J WangFull Text:PDF
GTID:2131330335473916Subject:Organic Chemistry
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A major challenge of modern drug discovery is to design of efficient chemical reaction sequences that provide maximum complexity and diversity with a minimum of synthetic steps. Recently Multi-component Reactions (MCRs) which is three or more different types of raw materials to form products directly without separation of intermediates, have emerged as a valuable synthetic tool in the context of modern drug discovery. A great variety of polycyclic compounds particularly many natural products can be formed in a higher yield than by conventional multistep synthesis. Multi-component reactions (MCRs) which is an important organic chemical reactions, is a simple, efficient materials easy to get, easy to automate, eco-friendly and high atom economy and other characteristics. In the design and synthesis of new drugs, combination chemical and natural products it has a wide range of uses. In recent years MCRs have received considerable attention from the organic community due to their advantages. On the basis of that pioneering works we have synthesized a series of heterocyclic compounds using Multi-component reactions.Firstly, According to multi-component reactions we summarized functions in organic synthesis as synthetic tools, such as three-component reactions four-component reactions and five-componnet reactions and so on. The reaction of multi-component involves Mannich Ractions, Cannizzaro Ractions and Ugi Ractions.The modern scientist's research focus on using environmental friendly solvents in organic synthesis, and it fits for the requirements of green chemistry. But even so, it will bring recycling and solvent treatment and other issues inevitably. Therefore, we are interesting in solvent-free reactions. In this paper, based on previous work, we successfully synthesized of 2-aminochromene derivatives and phthalazine derivatives under solvent-free conditions, and this method is applying to various substrates, simplicity of a"one-pot"procedure. Most of compounds were characterized by IR, 1HNMR and 13CNMR.2-Amino-4H-chromenes are important class of compounds found in many natural products and are widely used as cosmetics, pigments, and agrochemicals. The current interest in 2-amino-4H-chromene derivatives arises from their potential application in the treatment of rheumatoid and psoriatic arthritis to human inflammatory. We herein report a new method for the synthesis of 2-aminochromenes by the one-pot, three-component reaction of an aromatic aldehyde, malononitrile and naphthol in the presence of a catalytic amount of disodium hydrogen phosphate under solvent-free conditions.Heterocycles containing the phthalazine ring are important targets in synthetic and medicinal chemistry, phthalazine derivatives, which have two bridgehead nitrogen atoms in a fused ring system, possess antimicrobial, anticonvulsant anticancer, vasorelaxant and anti-inflammatory activities. Phthalazinone zopolrestat is a potent inhibitor of aldose reductase for catalytic and enantioselective alkyne addition. We describe a simple synthesis of 1H-indazolo[1,2-b]phthalazinetriones by three-component condensation reaction of aldehyde, dimedone, and phthalhydrazide in the presence of a catalytic amount of tungstosilicic acid under solvent-free conditions.The chromene derivatives are a class of important compounds, due to their biological activity, which have wide application in medicinal chemistry. Among these known bioactive chromenes, pyrano chromenes were of great interest. They are valuable synthons for the synthesis of pharmacological agents. We describe a simple procedure for the synthesis of dihydropyrano [3,2-c] chromene derivatives by three-component reaction of aldehydes, malononitrile, and 4-hydroxycoumarin in the presence of a catalytic amount of hexamethylenetetramine.Piperidine compounds which present in many natural products, are important drug molecule structural units, in the past decade,compounds containing piperidine rings have been used in pre-clinical and clinical trials. A highly atom-economic one-pot synthesis of functionalized tetrahydropyridines by a multicomponent condensation reaction ofβ-keto ester, two equivalents of aromatic aldehyde, and two equivalents of amine in the presence of a catalytic amount of cerium ammonium nitrate (CAN) is reported.As mentioned above four types of material containing nitrogen heterocyclic which play an important role are important compounds, so the research on nitrogen Heterocyclic Compounds is of great significance. We on the basis of previous research successfully synthesized the four substances, using"one pot"of Multi-component Reactions in the absence of solvent, ethanol, acetonitrile under reflux conditions, using cheap and easily obtained catalyst. The advantages of the method are suitable for various substrates, mild condition,operation and experimental simplicity,high yield. It will promote the development of organic synthesis chemistry.
Keywords/Search Tags:Multi-component, Reactions, 2-Amino-4H-chromenes, Phthalazine derivatives chromene derivatives Piperidines
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