Moussa Ziad, Ramanathan Mani, Al-Masri Harbi Tomah, Ahmed Saleh A
Department of Chemistry, College of Science, United Arab Emirates University, Al Ain P.O. Box 15551, United Arab Emirates.
Department of Chemistry, Faculty of Sciences, Al al-Bayt University, P.O. Box 130040, Mafraq 25113, Jordan.
Molecules. 2024 Dec 3;29(23):5710. doi: 10.3390/molecules29235710.
The development of efficient synthetic procedures to access fused N, O-heterocyclic skeletons has been a pivotal research topic in organic synthesis for several years. Owing to the applications of N, O-fused heterocycles in organic synthesis, material sciences, and medicinal chemistry, significant efforts have been dedicated to design novel methods for their construction. To this end, 1,3-benzoxazin-4-ones are privileged candidates for N, O-heterocyclic molecules often found in natural products, agrochemicals, and materials science applications. In this review, we aim to summarize the existing literature on the synthesis of 1,3-benzoxazin-4-ones from 2010 onwards. Moreover, 1,3-benzoxazin-4-ones have also been identified as an excellent native directing group for the ortho-functionalization via C-H activation, which is often a strenuous task requiring pre-functionalized substrates. In the latter part of this report, we compiled several interesting examples of -directed functionalizations of 1,3-benzoxazin-4-ones. Additionally, to emphasize biological importance, recent developments on the anticancer evaluations of benzoxazine-4-one core are included. We believe that by harnessing the methodologies discussed herein, new possibilities could be unlocked for the synthesis of fused N, O-heterocycles, leading to the development of novel biologically active compounds and functional materials.
多年来，开发高效的合成方法以构建稠合的氮、氧杂环骨架一直是有机合成领域的一个关键研究课题。由于氮、氧稠合杂环在有机合成、材料科学和药物化学中的应用，人们付出了巨大努力来设计构建它们的新方法。为此，1,3 - 苯并恶嗪 - 4 - 酮是氮、氧杂环分子的理想候选物，这些分子常见于天然产物、农用化学品和材料科学应用中。在这篇综述中，我们旨在总结2010年以来关于1,3 - 苯并恶嗪 - 4 - 酮合成的现有文献。此外，1,3 - 苯并恶嗪 - 4 - 酮也被确定为通过C - H活化进行邻位官能化的优良天然导向基团，而这通常是一项艰巨的任务，需要预官能化的底物。在本报告的后半部分，我们汇编了几个关于1,3 - 苯并恶嗪 - 4 - 酮导向官能化的有趣例子。此外，为了强调其生物学重要性，还纳入了苯并恶嗪 - 4 - 酮核心的抗癌评估的最新进展。我们相信，通过利用本文讨论的方法，可以为稠合氮、氧杂环的合成开辟新的可能性，从而推动新型生物活性化合物和功能材料的开发。
