Functionalized Triazines and Tetrazines: Synthesis and Applications

IF 7.1 2区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Joydip Mondal, Akella Sivaramakrishna
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引用次数: 9

Abstract

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.

Graphical Abstract

Abstract Image

功能化三嗪和四嗪:合成及应用
含有三嗪和四嗪基团的分子属于一类特殊的杂环化合物。三嗪和四嗪都是构建单元,为设计生物学上重要的有机分子提供了一个新的维度。它们的一些衍生物具有精细的电子特性,已被鉴定为多功能、适应性强、可切换、显著的抗真菌、抗癌、抗病毒、抗肿瘤、强心、抗hiv、镇痛、抗原虫等。本文综述了三嗪和四嗪分子的合成、配位性质及其应用的最新进展。丰富的文献展示了微波辅助、固相、金属基、[4+2]环加成和多组分一锅反应等多种合成三嗪和四嗪的途径。通过组合方法,合成方法包含线性、角化和融合的三嗪和四嗪杂环。值得注意的是,三嗪和四嗪经历了各种有机转化,包括亲电加成、偶联、亲核位移和分子内环化。对这些杂环的机理进行了详细的讨论。这些多嗪类化合物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。本文系统地综述了各种三嗪和四嗪体系的合成和潜在应用的最新进展和挑战。图形抽象
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来源期刊
Topics in Current Chemistry
Topics in Current Chemistry Chemistry-General Chemistry
CiteScore
13.70
自引率
1.20%
发文量
48
期刊介绍: Topics in Current Chemistry is a journal that presents critical reviews of present and future trends in modern chemical research. It covers all areas of chemical science, including interactions with related disciplines like biology, medicine, physics, and materials science. The articles in this journal are organized into thematic collections, offering a comprehensive perspective on emerging research to non-specialist readers in academia or industry. Each review article focuses on one aspect of the topic and provides a critical survey, placing it in the context of the collection. Selected examples highlight significant developments from the past 5 to 10 years. Instead of providing an exhaustive summary or extensive data, the articles concentrate on methodological thinking. This approach allows non-specialist readers to understand the information fully and presents the potential prospects for future developments.
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