Peglow Thiago J, Thomaz João Pedro S S C, Gomes Luana S, Nascimento Vanessa
SupraSelen Laboratory, Department of Chemistry, Universidade Federal Fluminense, Institute of Chemistry, Campus do Valonguinho, 24020-141 Niterói-RJ, Brazil.
ACS Omega. 2024 Dec 17;9(52):51295-51305. doi: 10.1021/acsomega.4c08079. eCollection 2024 Dec 31.
Our research presents selective direct selenylation at the C-4 pyrazole ring using KSO as an oxidant under simple and mild conditions. This elegant synthesis involves the one-pot method under acidic conditions, thus minimizing reaction steps and waste generation. This innovative method allowed us to create a library of 4-selanylpyrazoles in good to excellent yields. Furthermore, with slight changes in the protocol, we describe the synthesis of the unprecedented 4,5-bis-selanylpyrazole. The selectivity of the new insertion of organoselenium into the pyrazole core was demonstrated by several H and Se NMR experiments.
我们的研究展示了在简单温和的条件下,使用KSO作为氧化剂,在吡唑环的C-4位进行选择性直接硒化反应。这种精妙的合成方法涉及酸性条件下的一锅法,从而最大限度地减少了反应步骤和废物产生。这种创新方法使我们能够以良好至优异的产率创建一系列4-硒代吡唑化合物库。此外,通过对实验方案进行微小改变,我们描述了前所未有的4,5-双硒代吡唑的合成。通过多个氢核磁共振(H NMR)和硒核磁共振(Se NMR)实验证明了有机硒在吡唑核心中的新插入反应的选择性。