| Aryl C-N,C-O bonds widely exist in numerous important products in the fields of biological, pharmaceutical, and material sciences. Cross-coupling reactions are important methods to form these bonds. In the chapter one of this dissertation, based on the latest work about the copper-catalyzed cross-coupling reactions, a three component coupling reaction was developed to prepare diaryl ethers with nitrogenous substituent for the first time. In the model reaction of 4-bromphenyl iodide, caprolactam with phenol, with varied solvents, ligands, bases and the ratio between CuI and ligand, the reaction condition was optimized as follows: 15 mol% CuI, 20 mol% N,N-dimethyl- glycine, using K3PO4 as the base and DMSO as the solvent. Under these conditions, many functional groups such as keto, methoxy, and chloro need no protection and most of substrates could be transformed into the desired products in moderate to good yields. The hindered substrates also worked well. However, phenols bearing strong electron-withdrawing groups behaved poorly. In short, the advantages of this method include: the catalyst is cheap and environment-friendly; the scope of substrates is large; it is more easier to handle and more efficient than two-component reaction.CA-4 (Combretastatin A4) is a new cytotoxic agent (target in tubulin protein) as well as a tumor angiogenesis inhibitor. Furthermore, it is relatively inactive in normal tissues. Therefore, a lot of CA-4 derivatives have been synthesized and evaluated in recent years. In the chapter two of this dissertation, based on the research achievements about the SAR (Structure-Activity Relationship) of CA-4, a new kind of CA-4 derivative (the ethyleniclinkage of CA-4 anchored by heterocyclic ring) was proposed. And a new CA-4 derivative was synthesized fromβ-alanine by three-step reactions. In the future, we will synthesize a series of derivatives and evaluate their activity.
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