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Immobilized dithianylium salts and ylidene dithianes for the flexible syntheses of selectively labeled building blocks

固定化二噻烷基盐和亚基二噻烷用于选择性标记结构单元的灵活合成

基本信息

批准号：
262361502
负责人：
Professor Dr. Stefan Bräse
金额：
--
依托单位：
Institut für Organische Chemie (IOC)
依托单位国家：
德国
项目类别：
Research Grants
财政年份：
2014
资助国家：
德国
起止时间：
2013-12-31 至 2017-12-31
项目状态：
已结题

来源：
https://gepris.dfg.de/gepris/projekt/262361502?language=en
关键词：
Immobilized dithianylium salts ylidene dithianes

项目摘要

With this research project, we want to establish new procedures that allow the specific modification of dithiane derivatives on solid phases. By this, new concepts for the up to now often cumbersome introduction of fluorine and deuterium groups in aliphatic as well as heterocyclic building blocks shall be developed. Depending on the synthetic strategy, a selective construction of CDF2-, CHF2-, CD2F- or CF3-groups will be available on immobilized compounds that may offer further modifications for a diversity oriented synthesis. To expand this concept, the introduction of other electrophiles and nucleophiles in alpha- and beta-position will be investigated in order to synthesize a large number of diverse heterocyclic compounds on solid phases. The herein used dithiane derivatives (dithianylium ions and ylidene dithianes) shall allow the construction of novel functionalities on the core structure via a step by step protocol. In combination with various existing protocols (e.g. cyclizations) for modifications, the concept of immobilized dithiane derivatives provides perfect preconditions for solid phase-supported method development. Most of the method developing experiments will be done in solution and on solid phases to allow the investigation of the success of the reactions in both variants and to enhance basic knowledge in solution and solid phases via the direct comparison. Due to the use of the novel dithiane-based linkers, we will establish the basic knowledge for the selective synthesis of labeled and fluorinated compounds that are required in many fields (of research and beyond) and we will work on novel synthetic procedures for the construction of heterocyclic compounds. The results of the herein described work in form of the analytical data will be added during the project (and at least at its end) to the repository chemotion. Thereby, characterizations of the molecules are visible and available for all interested researchers for free.

通过这一研究项目，我们希望建立新的程序，允许二硫杂环戊烷衍生物在固相上进行特定的修饰。通过这一点，将开发出迄今为止在脂肪族和杂环构造物中引入氟基和重基通常很麻烦的新概念。根据合成策略的不同，可在固定化化合物上选择性地构建CDF2-、CHF2-、CD2F-或CF3-基团，这可能为以多样性为导向的合成提供进一步的修饰。为了扩展这一概念，将研究在α和β位置引入其他亲电性和亲核性，以便在固相上合成大量不同的杂环化合物。本文中使用的二硫代衍生物(二硫代锂离子和亚叶基二硫杂环戊烷)将允许通过逐步方案在核心结构上构建新的官能团。结合各种现有的修饰方案(如环化反应)，固定化二硫杂环戊烷衍生物的概念为固相支持的方法开发提供了完美的前提条件。大多数方法开发实验将在溶液和固相中进行，以便于研究这两个变体中反应的成功情况，并通过直接比较来增强溶液和固相中的基础知识。由于新型二硫杂环连接体的使用，我们将为许多领域(研究和其他领域)所需的标记和含氟化合物的选择性合成奠定基础，并将致力于构建杂环化合物的新合成方法。这里描述的工作的结果以分析数据的形式将在项目期间(以及至少在其结束时)添加到储存库化学中。因此，分子的表征是可见的，所有感兴趣的研究人员都可以免费获得。