Palaniraja Jeyakannu, Mohana Roopan Selvaraj, Mokesh Rayalu G, Abdullah Al-Dhabi Naif, Valan Arasu Mariadhas
Chemistry of Heterocycles & Natural Product Research Laboratory, Department of Chemistry, School of Advanced Sciences, VIT University, Vellore 632014, Tamilnadu, India.
G Mokesh Rayalu, Department of mathematics, School of Advanced Sciences, VIT University, Vellore 632014, Tamilnadu, India.
Molecules. 2016 Nov 18;21(11):1571. doi: 10.3390/molecules21111571.
This study deals with a new and efficient metal-free regioselective synthesis of pyrimido-fused indazoles with nitrogen ring junction motifs. We have developed a metal-free domino type reaction between 3-aminoindazole, aryl aldehydes and aceotophenones in the presence of KOH/DMF that leads to pyrimido[1,2-]indazole analogues. Response Surface Methodology (RSM) coupled with a Box-Behnken design (BBD) were utilized for exploring the effect of base used (A), temperature of reaction (B) and (C), reaction time. This approach can allow access to a variety of pyrimidoindazole fluorophores and related compounds. The compound -dimethyl-4-(2-phenylpyrimido[1,2-]indazol-4-yl)aniline () displays the maximum fluorescence intensity at 518 nm and shows a fluorescence quantum yield of 0.068. The synthesized pyramido-fused indazoles have been evaluated for their free radical scavenging activity and compound showed good antioxidant activity.
本研究涉及一种新型高效的无金属区域选择性合成含氮环连接基序的嘧啶并稠合吲唑的方法。我们在KOH/DMF存在下，开发了3-氨基吲唑、芳基醛和苯乙酮之间的无金属多米诺型反应，该反应可生成嘧啶并[1,2 -]吲唑类似物。采用响应面法（RSM）结合Box-Behnken设计（BBD）来探究所用碱（A）、反应温度（B）和（C）以及反应时间的影响。这种方法能够合成多种嘧啶并吲唑荧光团及相关化合物。化合物 -二甲基-4-(2-苯基嘧啶并[1,2 -]吲唑-4-基)苯胺（）在518 nm处显示出最大荧光强度，荧光量子产率为0.068。已对合成的嘧啶并稠合吲唑的自由基清除活性进行了评估，化合物显示出良好的抗氧化活性。
