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首页> 外文学位 >Inverse electron demand Diels-Alder reactions of imidazoles with heterocyclic azadienes and applications in the syntheses of heterocyclic natural products and scaffolds in chemical library development.
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Inverse electron demand Diels-Alder reactions of imidazoles with heterocyclic azadienes and applications in the syntheses of heterocyclic natural products and scaffolds in chemical library development.

机译：咪唑与杂环氮杂二烯的电子反需求Diels-Alder反应及其在化学文库开发中杂环天然产物和支架的合成中的应用。

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摘要

Various 2-position substituted imidazoles were employed as electron rich dienophiles in inverse electron demand Diels-Alder (IEDDA) chemistry with 1,2,4-triazines, leading to a variety of biologically interesting heterocyclic compounds. Intramolecular [4+2] cycloadditions of trimethylene-tethered imidazole/1,2,4-triazine pairs readily produced 1,2,3,4-tetrahydro-1,5-naphthyridines as a major product, instead of forming the anticipated deazapurines. Microwave-promoted cycloadditions of trimethylene-tethered imidazole/triazine pairs were briefly examined and showed promising results in promoting these cycloadditions. The intramolecular cycloadditions of imidazole/triazine pairs with four-methylene tethers were also successful, though these reactions were more sluggish than those with trimethylene tethers, and only worked under thermal conditions to provide 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines along with small yet reproducible amounts of aromatized deazapurines. Furthermore, all the cycloadditions were sensitive to substituent electronic effects.; Some of the 1,2,3,4-tetrahydro-1,5-naphthyridines were shown to be active against the drug resistant Mycobacterium avium complex, M. tuberculosis, as well as several fungal species. The efficiency and the ease of IEDDA methodology to prepare these naphthyridines together with their promising biological activities led to the use of these heterocycles as scaffolds to develop a diverse chemical library. Several reactions were tested mainly on the N-1 position of the tetrahydronaphthyridines to confirm the suitability of these heterocycles as library structural cores. Indeed, the N-1 position of the tetrahydronaphthyridines proved to be reactive, and a small 24-membered naphthyridine dimer library was successfully developed, setting the stage for a larger library.; In order to expand the scope and the application of this methodology, cycloadditions of imidazoles and isatin-derived 1,2,4-triazines were intended to synthesize the complete core of the grossularines, anticancer natural products with an alpha-carboline subunit. Extensive efforts were put in to this project, however, both inter- and intramolecular cycloadditions of imidazoles and isatin-derived 1,2,4-triazines were unsuccessful. Nevertheless, a novel and facile route to alpha-carbolines and 6H-indolo[2,3-b][1,5]naphthyridines by intramolecular IEDDA reactions between isatin-derived 1,2,4-triazines with alkynes and imidazoles, respectively, was developed.
机译：各种2位取代的咪唑被用作反电子需求Diels-Alder（IEDDA）化学中与1,2,4-三嗪的富电子亲二烯体，从而产生了多种生物学上有趣的杂环化合物。三亚甲基连接的咪唑/ 1,2,4-三嗪对的分子内[4 + 2]环加成反应很容易产生作为主要产物的1,2,3,4-四氢-1,5-萘啶，而不是形成预期的脱氮嘌呤。微波检测了三亚甲基束缚的咪唑/三嗪对的环加成反应，并在促进这些环加成反应中显示了令人鼓舞的结果。咪唑/三嗪对与四亚甲基醚的分子内环加成反应也很成功，尽管这些反应比三亚甲基醚更慢，并且仅在热条件下可提供2,3,4,5-四氢-1H-吡啶基[3,2-b] a庚因以及少量但可重现的芳香化脱氮嘌呤。此外，所有的环加成对取代基电子效应均敏感。 1,2,3,4-四氢-1,5-萘啶中的某些已显示对抗药性鸟分枝杆菌复合物结核分枝杆菌以及几种真菌具有活性。制备这些萘啶的IEDDA方法的效率和简便性及其有前途的生物活性导致使用这些杂环作为支架来开发各种化学文库。主要在四氢萘啶的N-1位置测试了几个反应，以确认这些杂环作为文库结构核心的适用性。确实，四氢萘啶的N-1位被证明具有反应性，并且成功开发了一个小的24元萘啶二聚体文库，为建立更大的文库奠定了基础。为了扩大该方法的范围和应用，咪唑和伊斯汀衍生的1,2,4-三嗪的环加成反应旨在合成具有α-咔啉亚基的抗癌天然产物grosularines的完整核心。对该项目进行了广泛的努力，但是，分子间和分子内的咪唑和伊斯汀衍生的1,2,4-三嗪均未成功。然而，通过伊斯兰衍生的1,2,4-三嗪分别与炔烃和咪唑之间的分子内IEDDA反应，可以轻松而新颖地制得α-咔啉和6H-吲哚并[2,3-b] [1,5]萘啶已开发。

著录项

  • 作者

    Woo, Grace Hyun Chong.;

  • 作者单位

    Boston University.;

  • 授予单位 Boston University.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 2005
  • 页码 250 p.
  • 总页数 250
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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