Topics in Current Chemistry ( IF 7.1 ) Pub Date : 2021-02-05 , DOI: 10.1007/s41061-020-00317-3 Ivan S Golovanov 1 , Alexey Yu Sukhorukov 1, 2
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Abstract
Cyclic boronate esters play important roles in organic synthesis, pharmacology, supramolecular chemistry and materials science owing to their stability in air and versatile reactivity. Most of these compounds contain a B–O–C linkage with an alkoxy- or carboxylate group bound to the boron atom (e.g. boronate-diol esters, MIDA boronates). Boron chelates comprising a B–O–N motif (BON heterocycles) are much less explored, although first representatives of this class were prepared in the early 1960s. In recent years, there has been a growing interest in BON heterocycles as new chemotypes for drug design. The exocyclic B–O–N linkage, which is readily formed under mild conditions, shows surprising hydrolytic and thermal resistance. This allows the formation of BON heterocycles to be used as click-type reactions for the preparation of bioconjugates and functionally modified polymers. We believe that BON heterocycles are promising yet underrated organoboron derivatives. This review summarizes the scattered information about known types of BON heterocycles, including their synthesis, reactivity and structural data. Available applications of BON heterocycles in materials science and medicinal chemistry, along with their prospects, are also discussed. The bibliography contains 289 references.
Graphic Abstract
中文翻译：
硼与氮-氧键的合并：BON杂环的综述
摘要
环状硼酸酯由于在空气中的稳定性和多种反应性，在有机合成，药理学，超分子化学和材料科学中起着重要的作用。这些化合物大多数都含有一个与硼原子相连的烷氧基或羧酸根基团的B–O–C键（例如硼酸酯，二醇酯，MIDA硼酸酯）。尽管1960年代初已经制备了此类的首批代表，但对包含B–O–N基序（BON杂环）的硼螯合物的研究却很少。近年来，人们对BON杂环作为药物设计的新化学型越来越感兴趣。在温和条件下容易形成的环外B-O-N键显示出令人惊讶的耐水解性和耐热性。这使得BON杂环的形成可用作制备生物缀合物和功能改性聚合物的点击型反应。我们相信，BON杂环是有前途但被低估的有机硼衍生物。这篇综述总结了有关已知类型的BON杂环的分散信息，包括其合成，反应性和结构数据。还讨论了BON杂环在材料科学和药物化学中的可用应用及其前景。参考书目包含289个参考文献。还讨论了BON杂环在材料科学和药物化学中的可用应用及其前景。参考书目包含289个参考文献。还讨论了BON杂环在材料科学和药物化学中的可用应用及其前景。参考书目包含289个参考文献。
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