Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology (VIT), Vellore, Tamil Nadu, 632 014, India.
Top Curr Chem (Cham). 2022 Jun 23;380(5):34. doi: 10.1007/s41061-022-00385-7.
The molecules possessing triazine and tetrazine moieties belong to a special class of heterocyclic compounds. Both triazines and tetrazines are building blocks and have provided a new dimension to the design of biologically important organic molecules. Several of their derivatives with fine-tuned electronic properties have been identified as multifunctional, adaptable, switchable, remarkably antifungal, anticancer, antiviral, antitumor, cardiotonic, anti-HIV, analgesic, anti-protozoal, etc. The objective of this review is to comprehensively describe the recent developments in synthesis, coordination properties, and various applications of triazine and tetrazine molecules. The rich literature demonstrates various synthetic routes for a variety of triazines and tetrazines through microwave-assisted, solid-phase, metal-based, [4+2] cycloaddition, and multicomponent one-pot reactions. Synthetic approaches contain linear, angular, and fused triazine and tetrazine heterocycles through a combinatorial method. Notably, the triazines and tetrazines undergo a variety of organic transformations, including electrophilic addition, coupling, nucleophilic displacement, and intramolecular cyclization. The mechanistic aspects of these heterocycles are discussed in a detailed way. The bioorthogonal application of these polyazines with various strained alkenes and alkynes provides a new prospect for investigations in chemical biology. This review systematically encapsulates the recent developments and challenges in the synthesis and possible potential applications of various triazine and tetrazine systems.
含有三嗪和四嗪部分的分子属于一类特殊的杂环化合物。三嗪和四嗪都是构建块,为设计具有重要生物学意义的有机分子提供了新的维度。它们的一些具有精细电子性质的衍生物已被确定为多功能、适应性强、可切换的,具有显著的抗真菌、抗癌、抗病毒、抗肿瘤、强心、抗 HIV、镇痛、抗原生动物等作用。本综述的目的是全面描述三嗪和四嗪分子的合成、配位性质和各种应用的最新进展。丰富的文献展示了通过微波辅助、固相、基于金属、[4+2]环加成和多组分一锅反应的各种合成路线来合成各种三嗪和四嗪。合成方法包括通过组合方法合成线性、角形和融合的三嗪和四嗪杂环。值得注意的是,三嗪和四嗪经历了多种有机转化,包括亲电加成、偶联、亲核取代和分子内环化。这些杂环的机理方面进行了详细的讨论。这些多嗪与各种应变烯烃和炔烃的生物正交应用为化学生物学的研究提供了新的前景。本综述系统地总结了各种三嗪和四嗪体系的合成以及可能的潜在应用的最新进展和挑战。