胍 (guanidines) 是一種具多種用途的藥理活性分子，因此在文獻上有許多方法被建立用來合成胍。而氰胺 (cyanamides ) 則是合成胍的前驅物，且氰胺也是一種抗腫瘤 (tumor inhibitors) 藥物。合成氰胺有許多方法，然而受限於合成條件的關係，在產率或是製備上均有其缺點。本論文首先開發合成氰胺的新方法，利用商業化且具立體障礙的鹼—雙(三甲基矽基)醯胺鈉 [NaN(SiMe3)2] 化合物和異硫氰酸酯進行反應，合成中高產率且具有藥理活性的氰胺化合物，此一新合成方法可應用於各種類型的異硫氰酸酯。接著我們藉著催化劑的使用，結合上述的新方法，建立一個新的一鍋反應來合成胍化合物；分子生物活性的篩檢資料顯示，有幾個我們合成出的胍分子在抗腫瘤測試上有不錯的效果。
吡唑為主體結構的衍生物已被研究出具有廣泛生物活性及藥理作用，近年來也有不少關於其在發光材料上應用的報導；基於吡唑分子的重要性，我們針對吡唑環上的鹵素原子，利用鈀催化劑[PdCl2(PPh3)2]將其氫化，得到高產率的吡唑分子，並做了一系列催化劑與其他條件的研究。最後為利用銅(CuI)催化系統來使5-胺基吡唑(5-aminopyrazole)與芳香鹵化物(arylhalide)進行碳氮鍵的偶合反應，我們找到一個適合的反應條件，來改善5-胺基吡唑其親核性較差的缺點，並能選擇性得到中高產率的兩種偶合產物。

The guanidinium group is present in many natural and synthetic biologically active compounds. Due to its broad spectrum of activity, the guanidine unit has been intensively studied as a synthetic goal and a diversity of new methods has been developed. Cyanamides are important precursors in the synthesis of guanidines. They also exhibit apparent tumor growth inhibition activity. Many of reagents are developed as a cyano cation (CN+) agent to synthesize the cyanamide products. Although their syntheses are straightforward, they do not produce quantitative yields and require tedious purification procedures. Herein, we report a transformation method of isothiocyanates to cyanamides using the commercially available alkali amide NaN(SiMe3)2. Additionally, we expanded the reaction to one pot synthesis of guanidines hydrochloride by using catalyst. Screening data indicated that several compounds exhibited significant in vitro activities against numerous human tumor cell.

Pyrazoles are an important family of heterocyclic compounds due to their wide range of pharmacological proprieties. In particular, modified pyrazoles are also the basis of various active material. For this reason, we report the use of palladium chloride in the presence of triphenylphosphine to remove the halogen atom in pyrazoles. The reaction went rapidly and efficiently. Finally, we have developed a new and efficient copper-catalyzed C-N bond formation for 5-aminopyrazoles with arylhalides. The reaction conditions for the copper-mediated N-arylation of heteroarylamines were optimized. The desired compounds of N-monoarylation or N-diarylation of 5-aminopyrazoles were synthesized in different reaction conditions.

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