New Synthetic Methodologies to Access N-Heterocycles
获取 N-杂环的新合成方法
基本信息
- 批准号:RGPIN-2014-05189
- 负责人:
- 金额:$ 3.93万
- 依托单位:
- 依托单位国家:加拿大
- 项目类别:Discovery Grants Program - Individual
- 财政年份:2018
- 资助国家:加拿大
- 起止时间:2018-01-01 至 2019-12-31
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
The proposed research falls in the category of synthetic organic chemistry, more specifically developing new reactions and methods of synthesis for application in natural products synthesis. We also propose to synthesize a new thermo- and photoresponsive scaffold to make molecular switches.*The proposed research is divided in four parts, the first is concerned with developing a new (4+1)-cycloaddition reaction of chromium aminocarbenes (CAMCs) destined to make 5-membered N-heterocycles. The latter are molecular fragments ubiquitously found in natural alkaloids. The second part is a new twist to the Nobel-Prize winning ring-closing metathesis (RCM) reaction: we have found and would like to exploit a newly discovered reaction of CAMCs to make dienamines. Such fragments can be very useful to make more complex N-heterocyclic structures. The third part is concerned with the photochemical or thermal ring-contraction of N-activated lactams. It is also aimed at making N-heterocycles and ultimately natural alkaloids. We propose to study, develop, and expand each methodology. Mechanistic aspects of the reactions will be probed to better understand them and thus be better able to control reactivity and selectivity issues. We also propose to use each method in total synthesis of natural alkaloids as a way to underscore their usefulness.*The last part of the proposed research is a venture into a new area of research in our laboratory. We believe we have discovered a new structural scaffold that could be used to make molecular switches. The scaffold is easily prepared and one such molecular scaffold, previously prepared for a totally different purpose, displayed the main attributes of a molecular switch: it isomerizes thermally and photochemically between two stable states. However, it needs to be studied and developed before we can call it a new thermo- and photoresponsive core structure. The synthesis is modular allowing for easy structural changes. We propose, at this stage, a proof of concept and will leave more complex studies and devices for a next discovery grant application.
拟议的研究福尔斯属于合成有机化学的范畴,更具体地说,开发新的反应和合成方法,用于天然产物的合成。我们还建议合成一种新的热响应和光响应支架来制造分子开关。本论文的研究工作分为四个部分,第一部分是发展一种新的氨基卡宾铬(CAMCs)的(4+1)-环加成反应,以制备五元N-杂环。后者是天然生物碱中普遍存在的分子片段。第二部分是一个新的转折诺贝尔奖获奖的闭环复分解(RCM)反应:我们已经发现,并希望利用一个新发现的反应CAMCs,使二烯胺。这样的片段对于制备更复杂的N-杂环结构非常有用。第三部分是关于N-活化内酰胺的光化学或热收缩环。它还旨在制造N-杂环并最终制造天然生物碱。我们建议研究、发展和扩展每一种方法。将探讨反应的机理方面,以更好地理解它们,从而能够更好地控制反应性和选择性问题。我们还建议在天然生物碱的全合成中使用每种方法,以强调它们的有用性。建议的研究的最后一部分是在我们的实验室进入一个新的研究领域的冒险。我们相信我们已经发现了一种新的结构支架,可以用来制造分子开关。这种支架很容易制备,而一种这样的分子支架,以前是为了完全不同的目的而制备的,显示了分子开关的主要属性:它在两种稳定状态之间进行热异构化和光化学异构化。然而,它需要研究和开发之前,我们可以称之为一个新的热和光响应的核心结构。合成是模块化的,允许容易的结构变化。在这个阶段,我们提出了一个概念证明,并将留下更复杂的研究和设备,为下一个发现补助金申请。
项目成果
期刊论文数量(0)
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Spino, Claude其他文献
Stereoselective Synthesis of (+)-Aspidofractinine
- DOI:
10.1021/jo9009497 - 发表时间:
2009-08-21 - 期刊:
- 影响因子:3.6
- 作者:
Gagnon, David;Spino, Claude - 通讯作者:
Spino, Claude
O-Heterocycles from Unsaturated Carbonyls and Dimethoxycarbene
- DOI:
10.1021/acs.joc.8b00613 - 发表时间:
2018-05-18 - 期刊:
- 影响因子:3.6
- 作者:
Croisetiere, Jean-Philippe;Spino, Claude - 通讯作者:
Spino, Claude
Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides:: Application to the total syntheses of alkaloids
- DOI:
10.1021/jo800817p - 发表时间:
2008-08-15 - 期刊:
- 影响因子:3.6
- 作者:
Lauzon, Sophie;Tremblay, Francois;Spino, Claude - 通讯作者:
Spino, Claude
N-Heteropolycyclic Compounds from the Formal Intramolecular (4+1)-Cycloaddition of Chromium Aminocarbenes
- DOI:
10.1021/ol4025887 - 发表时间:
2013-11-01 - 期刊:
- 影响因子:5.2
- 作者:
Dery, Martin;Lefebvre, Louis-Philippe D.;Spino, Claude - 通讯作者:
Spino, Claude
A Photorearrangement To Construct the ABDE Tetracyclic Core of Palau'amine
- DOI:
10.1021/acs.orglett.8b00819 - 发表时间:
2018-05-04 - 期刊:
- 影响因子:5.2
- 作者:
Aubert-Nicol, Samuel;Lessard, Jean;Spino, Claude - 通讯作者:
Spino, Claude
Spino, Claude的其他文献
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{{ truncateString('Spino, Claude', 18)}}的其他基金
Applying our synthesis skills : natural products and molecular machinery
应用我们的合成技能:天然产物和分子机械
- 批准号:
RGPIN-2019-05301 - 财政年份:2022
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
Applying our synthesis skills : natural products and molecular machinery
应用我们的合成技能:天然产物和分子机械
- 批准号:
RGPIN-2019-05301 - 财政年份:2021
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
Applying our synthesis skills : natural products and molecular machinery
应用我们的合成技能:天然产物和分子机械
- 批准号:
RGPIN-2019-05301 - 财政年份:2020
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
Applying our synthesis skills : natural products and molecular machinery
应用我们的合成技能:天然产物和分子机械
- 批准号:
RGPIN-2019-05301 - 财政年份:2019
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
New Synthetic Methodologies to Access N-Heterocycles
获取 N-杂环的新合成方法
- 批准号:
RGPIN-2014-05189 - 财政年份:2017
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
New Synthetic Methodologies to Access N-Heterocycles
获取 N-杂环的新合成方法
- 批准号:
RGPIN-2014-05189 - 财政年份:2016
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
New Synthetic Methodologies to Access N-Heterocycles
获取 N-杂环的新合成方法
- 批准号:
RGPIN-2014-05189 - 财政年份:2015
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
New Synthetic Methodologies to Access N-Heterocycles
获取 N-杂环的新合成方法
- 批准号:
RGPIN-2014-05189 - 财政年份:2014
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
The (4+1)-cycloaddition of electron-rich carbenes / la cycloaddition-(4+1) de carbènes riches en électrons
富电子卡宾的 (4 1)-环加成 / la cycloaddition-(4 1) de carbènes riches en électrons
- 批准号:
180845-2009 - 财政年份:2013
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
The (4+1)-cycloaddition of electron-rich carbenes / la cycloaddition-(4+1) de carbènes riches en électrons
富电子卡宾的 (4 1)-环加成 / la cycloaddition-(4 1) de carbènes riches en électrons
- 批准号:
180845-2009 - 财政年份:2012
- 资助金额:
$ 3.93万 - 项目类别:
Discovery Grants Program - Individual
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