肼基二硫代甲酸甲酯席夫碱的合成

肼基二硫代甲酸甲酯席夫碱的合成

摘要

席夫碱类化合物在药学、催化、分析化学、防腐蚀以及光致变色领域都有重要的应用。多种研究表明席夫碱结构具有重要的生物学意义。肼基二硫代甲酸甲酯席夫碱是合成缩氨硫脲的重要中间体，可由肼基二硫代甲酸甲酯与醛、酮反应得到，产品易于纯化，性质稳定，产率较高，并且研究表明其本身具有一定的抗癌活性。为合成含其他杂环的缩氨基硫脲化合物，本论文设计并合成了一系列肼基二硫代甲酸甲酯席夫碱中间体。

目标产品的合成主要分两步进行：第一步是肼基二硫代甲酸甲酯的合成，对合成过程进行了分析，讨论了可能形成的杂质及提高产率的方法；第二步为肼基二硫代甲酸甲酯席夫碱的合成。对所合成产品进行了熔点的测定和氢核磁谱的表征。

关键词：肼基二硫代甲酸甲酯，席夫碱，核磁，表征

The synthesis of methyl hydrazinecarbodithioate Schiff bases

Abstract

Schiff base compounds have important applications in pharmaceutical, catalysis, analytical chemistry, corrosion and photo chromic fields. Many studies show that the schiff base structure has vital biological importance. Methyl hydrazinecarbodithioate is an important intermediate to synthesis thiosemicarbazones, which can be obtained by the reaction of methyl hydrazinecarbodithioate with aldehydes or ketones, and they are easy to be purified and stable. There is evidence that methyl hydrazinecarbodithioate Schiff base has certain anti-cancer activity too. In order to obtain other thiosemicarbazones containing heteroatom, a series of methyl hydrazinecarbodithioate Schiff bases were designed and synthesized.

The synthesis of target products was divided into two parts: the synthesis of methyl hydrazinecarbodithioate is the first step, furthermore, the synthetic process was analyzed as well as impurities and the methods of enhancing the yields; the preparation of methyl hydrazinecarbodithioate Schiff base is the second step. In this article, the synthetic products were characterized by melting point determination and 1H NMR.

Keyword: methyl hydrazinecarbodithioate, Schiff base, 1H NMR, characterization

目录

1 绪论 (1)

1.1 引言 (1)

1.2 席夫碱的合成及应用概况 (2)

1.2.1 席夫碱化合物在发光材料领域的应用 (2)

1.2.2 席夫碱化合物在医药领域的应用 (3)

1.2.3 席夫碱化合物在防腐蚀领域的应用 (7)

1.2.4 席夫碱化合物在催化领域的应用 (7)

1.3 肼基二硫代甲酸甲酯席夫碱的合成及生物活性研究 (8)

2实验部分 (10)

2.1试剂与仪器 (10)

2.1.1 试剂 (10)

2.1.2 仪器 (10)

2.2 原料的制备 (11)

2.2.1 肼基二硫代甲酸甲酯1的制备 (11)

2.3 产物的制备 (11)

2.3.1 3-苯基乙撑肼基二硫代甲酸甲酯2的制备 (11)

2.3.2 3-（吡啶基乙撑）肼基二硫代甲酸甲酯3的制备 (12)

2.3.3 3-（吡嗪基乙撑）肼基二硫代甲酸甲酯4的制备 (12)

2.3.4 3-（2-羟基苯基甲撑）肼基二硫代甲酸甲酯5的制备 (13)

2.3.5 3-（3’,5’-二叔丁基-2-羟基苯基甲撑）肼基二硫代甲酸甲酯6的制备.. 13 2.3.6 3-（5’-氯-2’-羟基苯基甲撑）肼基二硫代甲酸甲酯7的制备 (13)

2.3.7 3-（3’,5’-二溴-2-羟基苯基甲撑）肼基二硫代甲酸甲酯8的制备 (14)

3结果与讨论 (15)

3.1 核磁共振 (15)

3.1.1 核磁共振的产生与核磁共振谱 (15)

3.1.2 化学位移 (15)

3.2 肼基二硫代甲酸甲酯的合成及产物的表征 (16)

3.2.1 肼基二硫代甲酸甲酯的合成 (16)

3.2.2 产物的表征 (17)

3.3 合成机理 (22)

结论 (23)

参考文献 (24)