A Cycloaddition Protocol For the Synthesis of Functionalised Heteroaromatic Boronic Esters

合成官能化杂芳硼酯的环加成方案

• 批准号: EP/E016898/1
• 负责人: Joseph Harrity
• 金额: $ 29.71万
• 依托单位: University of Sheffield
• 依托单位国家: 英国
• 项目类别: Research Grant
• 财政年份: 2007
• 资助国家: 英国
• 起止时间: 2007 至 无数据
• 项目状态: 已结题
• 来源: https://gtr.ukri.org/projects?ref=EP%2FE016898%2F1
• 关键词: Cycloaddition; Protocol; Synthesis; Functionalised; Heteroaromatic

Increasing pressure on the Fine Chemicals Industry to produce novel therapeutics with an efficacious clinical profile but within a shorter timeframe has revolutionised medicinal chemistry over the last decade. In particular, the acquisition of structure activity relationships (SAR) data, the primary means by which medicinal chemists design new potential bioactive molecules, has been significantly promoted by the advent of high throughput synthesis techniques. A key element of this drug discovery process is the availability of starting compounds that bear useful functionality for further elaboration, such that a systematic investigation of the biological and physiochemical properties can be made. In this context, we have embarked upon a programme of research in our labs to develop a new strategy to aromatic and heteroaromatic boronic esters. These compounds are amongst the most valuable synthetic intermediates in modern organic chemistry. They are used throughout both industry and academia, largely because of their ability to form carbon-carbon bonds to various aromatic substrates through a Pd-catalysed cross-coupling reaction. Despite their popularity, their synthesis can be rather arduous, especially if one wishes to generate complex analogues. In an effort to address these limitations, this proposal sets out to use cycloaddition reactions of readily available alkynylboronates to prepare highly functionalised aromatic and heteroaromatic boronic esters.

精细化学品行业面临越来越大的压力，要求在更短的时间内生产具有有效临床特征的新型疗法，这在过去十年中彻底改变了药物化学。特别是，结构活性关系（SAR）数据的获取是药物化学家设计新的潜在生物活性分子的主要手段，高通量合成技术的出现极大地促进了这种数据的获取。该药物发现​​过程的一个关键要素是起始化合物的可用性，这些化合物具有用于进一步阐述的有用功能，以便可以对生物和理化特性进行系统研究。在这种背景下，我们在实验室开展了一项研究计划，以开发芳香族和杂芳香族硼酸酯的新策略。这些化合物是现代有机化学中最有价值的合成中间体之一。它们在工业界和学术界得到广泛应用，主要是因为它们能够通过钯催化的交叉偶联反应与各种芳香族底物形成碳-碳键。尽管它们很受欢迎，但它们的合成可能相当困难，特别是如果人们希望生成复杂的类似物。为了解决这些限制，该提案提出使用易于获得的炔基硼酸酯的环加成反应来制备高官能化的芳香族和杂芳香族硼酸酯。