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Synthesis Of 1,3-Disubstituted Indolizine Compounds

Posted on:2012-10-07Degree:MasterType:Thesis
Country:ChinaCandidate:J J SunFull Text:PDF
GTID:2181330335468254Subject:Organic Chemistry
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Organic Chemistry of heterocyclic chemistry has been very active in one of the areas, and heterocyclic compounds because of their good biological activity by organic chemists of all ages. Indolizine compounds which belong to a class of cyclization of nitrogen are that five-membered ring bicyclic system and share a six-membered ring nitrogen heterocycles, the effective synthesis method has been the focus of attention. Today, organic chemistry is moving towards environmentally friendly, easy to operate atom economy in areas such as development. Response and multiple-component cascade reaction afford the atom efficiency and green chemistry, etc., and developed a new type of synthetic strategy, we want to develop a simple and easy to get the compound to the substrate in the direct synthesis of indolizine approach.This paper more a very detailed overview of indolizine synthesis in recent years including the synthesis of five-membered ring structure of indolizine, indolizine six-membered ring structure and the structure of the nitrogen both in the five- membered rings and six-membered ring synthesis. Indolizine compounds as well drug activity, has potential applications in many areas, therefore we propose the idea of the synthesis of these compounds.Based on the study of the a-iodide reaction in our research team, we have a simple easy to get the aromatic ketones as the starting material B by the reaction of a-iodination of a-iodo ketones without intermediate separation and purification, to continue Nitrile and allyl (allyl ester), pyridine (4-methyl-pyridine) by 1,3-dipolar cycloaddition in the synthesis of indolizine derivatives. We proposed the reaction mechanism hypothesis, the target molecular structure by the 1H NMR,13C NMR, IR and HRMS and other characterization, in which the compoundsⅡ-2c has also been confirmed by the crystal structure.Finally, we conducted the research based on glycoluril diethyl heterocyclic synthesis and analysis of crystal. Due to the good application performance of glycoluril molecular in host-guest chemistry in a very in recent years, the first time in this chapter aromatic amines and ethyl-based glycoluril apply to such reactions. All the target compounds were characterized by the 1H NMR,13C NMR, IR and HRMS. In addition, we use X-ray diffraction confirms the structure of productsⅢ-4d and conformation. Research in this area provides the basis of preparation for the next studys for their physiological activity.
Keywords/Search Tags:Indolizine, α-iodide reaction, 1, 3-Dipolar cycloaddition, aromatic amines, diethoxycarbonyl glycoluril(DEG)
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