摘要
以1-苯基-3-甲基-5-苯氧基-吡唑-4-甲醛为原料,与苯乙酮(取代苯乙酮)发生羟醛缩合,生成相应的查尔酮,再在冰醋酸中与不同的肼反应,高产率的合成出10种新的5位含1-苯基-3-甲基-5-苯氧基-吡唑基的吡唑啉类衍生物。冰乙酸既是反应溶剂,又是催化剂,产率最高可达72%。目标化合物的结构经元素分析、红外光谱和核磁共振测试技术加以确认。化合物的荧光测定证明,化合物3a^3e发射紫色荧光,λem约为377 nm,化合物4a^4e发射蓝色荧光,λem约为480 nm。在荧光光谱中,不同取代基的联吡唑啉类化合物表现出不同的荧光强度,其中化合物4e具有最强的荧光发射,其强度值可达到4694。所合成出的化合物是一类较好的联吡唑啉类荧光化合物。
Five chalcones were synthesized via the aldol condensation reaction of acetophenone or parasubstituted acetophenones with 1-phenyl-3-methyl-5-phenoxyl-pyrazol-4-aldehyde, which reacted with two kinds of hydrazine in glacial acetic acid under refluxing to give a series of bipyrazoline derivatives. In this synthetic course, glacial acetic acid is not only a solvent, but also a catalyzer. An optimal yield of 72% was achieved when the reaction was carried out in refluxing. The structures of the compounds were confirmed by means of IR spectrum, I H NMR and elemental analysis. The fluorescent spectra of the prepared compounds show that compounds 3a -3e emits blue fluorescence, the emission wavelength was at about 377 nm. Compounds 4a -4e emits purple fluorescence, the emission wavelength was at about 480 nm. In the fluorescence spectrum, the bipyrazoline compounds of different substituents have diferent fluorescence intensity, compound 4e shows a maximum fluorescence intensity of 4 694. The results show that the compounds may be better fluorescence materials.
出处
《应用化学》
CAS
CSCD
北大核心
2007年第7期765-769,共5页
Chinese Journal of Applied Chemistry
基金
国家自然科学基金(20562011)
新疆大学青年启动基金资助项目
关键词
查尔酮
联吡唑啉
荧光性能
chalcone, bipyrazoline, fluorescent compound
