Abeed Ahmed A O, El-Emary Talaat I, Youssef Mohamed S K
Department of Chemistry, Faculty of Science, Assiut University, Assiut 71516, Egypt.
Curr Org Synth. 2019;16(3):405-412. doi: 10.2174/1570179416666181210160908.
This work presents the synthetic capability and the exploitation of 1,3-diphenyl- 1H-pyrazole-4-carboxladehyde 1 and 5-diphenyl pyrazolyl-2-pyrazoline analogue 8 to serve as excellent precursors for the synthesis of substituted indol-2,3-dione, trizolo[3,4-a]benzazoles, thiazolo[2,3- a]benzimidazole-3-one, substituted 2-pyrazoline and pyrazole-substituted-pyrazolines using various reagents.
Using chemicals from Aldrich, Fluka, or Merck, and pure solvents, we apply the synthetic procedures for the synthesis of novel heterocycles. The melting points of these compounds were determined using APP. Digital ST 15 melting point apparatus. SP3-100 spectrophotometer recorded FT-IR spectra (KBr) (cm-1). NMR spectra (δ, ppm) were recorded on 400 MHz AVANCE-III High-Performance FT-NMR Spectrometer BRUCKER (Switzerland) and some 1H NMR spectra were recorded on Varian EM-360L NMR Spectrophotometer (90 MHz) (USA) in CDCl3 or DMSO-d6 as a solvent. Elemental analyses were carried out at a Vario EL C, H, N, and S Analyzer. Bromine was determined using direct titration method after carius combustion.
The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analyses.
1,3-Diphenyl-1H-pyrazole-4-carboxladehyde 1 and 2-pyrazoline derivative 9 confirmed their importance in the synthetic organic chemistry. Depending on the formyl group of aldehyde 1 and active methylene of pyrazoline 8, we synthesized new series of heterocycles; indol-2,3-dione, trizolo[3,4-a]benzazole, thiazolo[2,3-a]benzimidazole-3-one and pyrazolyl-pyrazoline derivatives expecting their pharmacological applications. The targeted compounds were substantiated from its spectral data.
本研究展示了1,3 - 二苯基 - 1H - 吡唑 - 4 - 甲醛1和5 - 二苯基吡唑基 - 2 - 吡唑啉类似物8的合成能力及其作为优异前体的应用，可用于使用各种试剂合成取代的吲哚 - 2,3 - 二酮、三唑并[3,4 - a]苯并唑、噻唑并[2,3 - a]苯并咪唑 - 3 - 酮、取代的2 - 吡唑啉和吡唑取代的吡唑啉。
使用来自Aldrich、Fluka或Merck的化学试剂以及纯溶剂，我们应用合成程序来合成新型杂环化合物。这些化合物的熔点使用APP Digital ST 15熔点仪测定。SP3 - 100分光光度计记录FT - IR光谱（KBr）（cm⁻¹）。NMR光谱（δ，ppm）在400 MHz AVANCE - III高性能FT - NMR光谱仪BRUCKER（瑞士）上记录，部分¹H NMR光谱在Varian EM - 360L NMR分光光度计（90 MHz）（美国）上以CDCl₃或DMSO - d₆作为溶剂记录。元素分析在Vario EL C、H、N和S分析仪上进行。溴在卡里乌斯燃烧后使用直接滴定法测定。
化合物的结构通过IR、¹H NMR、¹³C NMR和元素分析得以确认。
1,3 - 二苯基 - 1H - 吡唑 - 4 - 甲醛1和2 - 吡唑啉衍生物9证实了它们在有机合成化学中的重要性。基于醛1的甲酰基和吡唑啉8的活性亚甲基，我们合成了一系列新的杂环化合物；吲哚 - 2,3 - 二酮、三唑并[3,4 - a]苯并唑、噻唑并[2,3 - a]苯并咪唑 - 3 - 酮和吡唑基 - 吡唑啉衍生物，并期望它们具有药理学应用。目标化合物通过其光谱数据得到证实。
