Maurya Anand, Patel Upendra Kumar, Kumar Sanjeev, Agarwal Alka
Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University Varanasi-221005 Uttar Pradesh India
RSC Adv. 2024 Sep 18;14(40):29505-29517. doi: 10.1039/d4ra05443a. eCollection 2024 Sep 12.
The present work has developed a straightforward, gentle, and effective approach for synthesizing arylamines and 5-substituted-1-tetrazole derivatives, and among the two tested catalysts, molybdenum trioxide (MoO) proved to be highly effective. The selective hydrogenation of nitroarenes to arylamines presents a significant challenge due to the complex reaction mechanism and the competitive hydrogenation of other reducible functional groups. It facilitated the transfer hydrogenation of nitrobenzene using hydrazine hydrate-produced amino compounds and enabled the [3 + 2] cycloaddition of sodium azide with aromatic nitriles to yield 5-substituted-1-tetrazoles. The structure of compound 5-(4-bromophenyl)-1-tetrazole (5k) was verified through single-crystal X-ray analysis, and the calculation of Green Chemistry Metrics showed the optimal range. Notably, the MoO catalyst can be reutilized for up to seven cycles with minimal loss of effectiveness. These attributes make molybdenum trioxide particularly attractive for industrial applications. This methodology offers several advantages over traditional synthetic methods.
本研究开发了一种简单、温和且有效的方法来合成芳胺和5-取代-1-四唑衍生物,在两种测试催化剂中,三氧化钼(MoO)被证明是高效的。由于反应机理复杂以及其他可还原官能团的竞争性氢化,将硝基芳烃选择性氢化为芳胺面临重大挑战。它促进了使用水合肼生成氨基化合物对硝基苯的转移氢化,并使叠氮化钠与芳腈发生[3 + 2]环加成反应生成5-取代-1-四唑。通过单晶X射线分析验证了化合物5-(4-溴苯基)-1-四唑(5k)的结构,绿色化学指标计算显示了最佳范围。值得注意的是,MoO催化剂可重复使用多达七个循环,而有效性损失最小。这些特性使三氧化钼对工业应用特别有吸引力。该方法相对于传统合成方法具有几个优点。