Direct methods for the preparation of heterocycles and bis-heteroaromatics

制备杂环和双杂芳族化合物的直接方法

• 批准号: EP/E020607/1
• 负责人: Nicholas Tomkinson
• 金额: $ 28.86万
• 依托单位: CARDIFF UNIVERSITY
• 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%2FE020607%2F1
• 关键词: Direct; methods; preparation; heterocycles; bis

Within this project we will develop new reagent based methodology to provide simple, robust and highly practical synthetic methods of broad applicability within organic synthesis. N-Methyl-O-tosyl hydroxylamine will provide a new method for the direct conversion of both aldehydes and ketones to alpha-oxysulfonyl carbonyl compounds, which, when treated directly with a variety of bis-hetero nucleophiles in-situ will provide a one-pot reaction sequence to access a variety of biologically significant heterocycles. Buchwald coupling of N-methyl-O-benzoyl hydroxylamine (and analogues) with aryl halides will lead to a cascade reaction sequence to provide direct access to bis-functionalised heteroaromatics which are present in a wide variety of both synthetic and naturally occurring compounds of biological importance. Application of these new methods to the praparation of targeted chemical arrays will provide access to a series of densely functionalised products for biological assay.

在这个项目中，我们将开发新的基于试剂的方法，以提供简单，强大和高度实用的合成方法，广泛适用于有机合成。N-甲基-O-对甲苯磺酰基羟胺将提供一种将醛和酮直接转化为α-氧磺酰基羰基化合物的新方法，当直接与各种双杂亲核试剂原位处理时，将提供一锅反应序列以获得各种生物学上重要的杂环。N-甲基-O-苯甲酰基羟胺（和类似物）与芳基卤化物的Buchwald偶联将导致级联反应序列，以提供直接获得双官能化杂芳族化合物的途径，所述双官能化杂芳族化合物存在于多种具有生物重要性的合成和天然存在的化合物中。应用这些新方法制备靶向化学阵列将提供一系列用于生物测定的密集功能化产品。

项目成果

Palladium-Catalyzed Coupling of Hydroxylamines with Aryl Bromides, Chlorides, and Iodides

• DOI: 10.1021/ol8025022
• 发表时间: 2009-01-01
• 期刊: ORGANIC LETTERS
• 影响因子: 5.2
• 作者: Porzelle, Achim;Woodrow, Michael D.;Tomkinson, Nicholas C. O.
• 通讯作者: Tomkinson, Nicholas C. O.