不同氮源制备无叠氮化物1,2,3-三唑的研究进展。

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC
Xinxin Zhou and Changchun Liu
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引用次数: 0

摘要

1,2,3-三唑是一类重要的五元氮杂环化合物,具有良好的生物活性和材料性质,在药物开发、功能材料和农用化学品等方面具有广泛的应用潜力。虽然使用叠氮化物的传统合成方法已经建立,但它们面临固有的局限性,包括与有机叠氮化物相关的爆炸危险和有限的官能团耐受性。近年来,利用替代氮源(如腙、重氮化合物和亚硝酸盐酯/盐)的新合成策略已经被开发出来。这些方法利用多种反应途径,包括[3 + 2]环加成、分子内偶联、重排-环化、光/电催化氧化和多组分偶联,从而有效地构建结构多样的三唑衍生物。本文系统总结了基于不同氮源的1,2,3-三唑环的构建策略,重点介绍了2017 - 2025年的研究进展。通过对反应机理、效率、官能团耐受性和安全性的深入探讨,批判性地分析了每种方法的优点和局限性。对未来的研究方向进行了展望,优先考虑更安全的氮源(如肟)、非贵金属催化、计算辅助的机理研究、一锅串联反应和高级三唑衍生物的靶向合成(如氟化或融合环)。本研究旨在为安全、高效、可持续、可扩展地合成功能化1,2,3-三唑衍生物提供有价值的参考。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Recent advances in azide-free 1,2,3-triazole construction from diverse nitrogen sources

Recent advances in azide-free 1,2,3-triazole construction from diverse nitrogen sources

1,2,3-Triazoles represent an important class of five-membered nitrogen heterocycles, exhibiting promising biological activities and material properties that underpin their broad application potential in drug discovery, functional materials, and agrochemicals. While traditional synthetic methods employing azides are well-established, they face inherent limitations, including explosion hazards associated with organic azides and restricted functional group tolerance. In recent years, novel synthetic strategies utilizing alternative nitrogen sources—such as hydrazones, diazo compounds, and nitrite esters/salts—have been developed. These approaches leverage diverse reaction pathways, including [3 + 2] cycloadditions, intramolecular couplings, rearrangement-cyclizations, photo-/electro-catalytic oxidations, and multicomponent couplings, enabling efficient construction of structurally diverse triazole derivatives. This review systematically summarizes strategies for constructing the 1,2,3-triazole ring based on distinct nitrogen sources, focusing primarily on advances from 2017 to 2025. Through in-depth exploration of reaction mechanisms, efficiency, functional group tolerance, and safety, the advantages and limitations of each methodology are critically analyzed. Perspectives on future research directions are also discussed, prioritizing safer nitrogen sources (e.g., oximes), non-precious-metal catalysis, mechanistic studies aided by computation, one-pot tandem reactions, and targeted synthesis of advanced triazole derivatives (e.g., fluorinated or fused-ring). This work aims to provide mechanistic insights and serve as a valuable reference for the safe, efficient, sustainable, and scalable synthesis of functionalized 1,2,3-triazole derivatives.

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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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