Novel syntheses of functionalized indoles, quinolines, and isoquinolines

功能化吲哚、喹啉和异喹啉的新合成

• 批准号: 9232361
• 负责人: BJORN C SODERBERG
• 金额: $ 44万
• 依托单位: WEST VIRGINIA UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 2016
• 资助国家: 美国
• 起止时间: 2016-09-15 至 2022-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/9232361
• 关键词: Academia; Alkaloids; Alkenes; Area; Biological; Complex; Cyclization; Development; Experimental Designs; Goals; Heterocyclic Compounds; Indoles; Industry; Isoquinolines; Laboratories; Mediating; Methodology; Methods; Oxides; Palladium; Participant; Pharmacologic Substance; Public Health; Reaction; Reagent; Research; Route; Scientist; Side; Solvents; Source; Students; System; Time; Training; Work; base; catalyst; drug candidate; expectation; flexibility; functional group; graduate student; innovation; interest; novel; pyrroloquinoline; quinoline; scaffold; undergraduate student

Project Summary The objective of this proposal is to develop innovative new synthetic methodologies for the synthesis of indole, quinoline, and isoquinoline scaffolds. It is anticipated that the methodologies proposed would furnish simple, mild, and flexible synthetic routes to an array of functionalized indoles, N-hydroxy, N-alkoxyindoles, quinolines, quinoline N- oxides, isoquinolines, and isoquinoline N-oxides. The research is of relevance to synthetic, medicinal, and pharmaceutical chemists and scientists in related fields both in industry and academia. The proposed work is divided into four sections each describing a novel methodology for expedient synthesis of functionalized heterocyclic compounds. In the first section, palladium catalyzed, base and CO mediated, indole/quinoline/isoquinoline syntheses will be presented together with a short synthesis of pyrroloquinolines alkaloids. The second section expands on the first section into the synthesis of 4-arylquinolines and applications in pyridoacridine alkaloid synthesis. Photochemically induced, palladium catalyzed, reactions will be examined in the third section, with the expectation of the development of complementary, mild, methodologies. Finally, base-mediated reactions to N-oxygenated ring systems in the absence of a catalyst will be studied in the fourth section. The participants, other that the PI, on the project will be one undergraduate student (3 months during each summer for three years) and two graduate students (full time for 3 years). The students will be trained in state of the art organic and organometallic synthesis including experimental design and execution, product purification, and product identification and characterization by spectroscopical means (NMR, IR, HRMS, UV-VIS, etc.).

项目摘要 这项提议的目标是开发创新的新的合成方法 用于合成吲哚、喹啉和异喹啉支架。据预计， 建议的方法将提供简单、温和和灵活的合成路线 官能化吲哚，N-羟基，N-烷氧基吲哚，喹啉，喹啉N- 氧化物、异喹啉和异喹啉N-氧化物。这项研究与以下方面有关 相关领域的合成、药物和药物化学家和科学家 工业界和学术界。 拟议的工作分为四个部分，每个部分描述了一种新的方法 用于官能化杂环化合物的简便合成。在第一节中， 钯催化、碱和CO催化的吲哚/喹啉/异喹啉合成 将与一段简短的吡咯喹啉生物碱的合成一起介绍。这个 第二节在第一节的基础上扩展到4-芳基喹啉的合成和 在吡啶生物碱合成中的应用。光化学诱导的钯 在催化下，反应将在第三节中进行审查，期望 开发补充的、温和的方法。最后，碱基介导的反应 第四章将研究无催化剂条件下的TO-N-氧代环体系 一节。 该项目的参与者，除PI外，将是一名本科生(3 三年中每年暑假的几个月)和两个研究生(全日制三年 年)。学生将接受最先进的有机和有机金属的培训。 综合包括实验设计和实施、产品提纯和产品 利用光谱手段(核磁共振、红外光谱、高分辨质谱、紫外-可见光谱、 等)。

项目成果

Syntheses of three naturally occurring polybrominated 3,3'-bi-1H-indoles.

• DOI: 10.1016/j.tetlet.2017.01.103
• 发表时间: 2017-03-15
• 期刊: Tetrahedron letters
• 影响因子: 1.8
• 作者: Ansari NH;Taylor MC;Söderberg BCG
• 通讯作者: Söderberg BCG

Palladium-Catalyzed Double Reductive Cyclization of 2,3-Dinitro-1,4-dialkenylbenzenes. Synthesis of 1H,8H-Pyrrolo[3,2-g]indoles.

• DOI: 10.1021/acs.joc.9b03290
• 发表时间: 2020-03-20
• 期刊: JOURNAL OF ORGANIC CHEMISTRY
• 影响因子: 3.6
• 作者: Ansari, Nurul H.;Banini, Serge;Cummings, Matthew M.;Soderberg, Bjorn C. G.
• 通讯作者: Soderberg, Bjorn C. G.

Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin.

• DOI: 10.1016/j.tet.2018.02.051
• 发表时间: 2018-05-24
• 期刊: Tetrahedron
• 影响因子: 2.1
• 作者: Ansari NN;Cummings MM;Söderberg BCG
• 通讯作者: Söderberg BCG

A palladium-catalyzed Barluenga cross-coupling - reductive cyclization sequence to substituted indoles.

• DOI: 10.1016/j.tet.2021.132331
• 发表时间: 2021-08
• 期刊: Tetrahedron
• 影响因子: 2.1
• 作者: S. Rahman;Björn C. G. Söderberg

Synthesis of the tricyclic indole alkaloids, dilemmaones A and B.

三环吲哚生物碱、困境 A 和 B 的合成。

• DOI: 10.1016/j.tet.2019.130714
• 发表时间: 2019
• 期刊: Tetrahedron
• 影响因子: 2.1
• 作者: Lambson,KatharineE;Dacko,ChristopherA;McNeill,JeffreyM;Akhmedov,NovruzG;Söderberg,BjörnCG
• 通讯作者: Söderberg,BjörnCG