Name: synthesis of antiviral tetrahydrocarbazole derivatives by photochemical and acid-catalyzed c-h functionalization via intermediate peroxides (chips)
Uploaded: 2014-06-20T14:00:00
Description: Watch this Scientific Journal Video about Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS at JoVE.com

Financial support from the DFG (Heisenberg scholarship to M.K., KL 2221/4-1; KL 2221/3-1) and the Max-Planck-Institut fuer Kohlenforschung is gratefully acknowledged.

Tetrahydrocarbazole 과산화물의 1. 합성 <ol><li> tetrahydrocarbazole 매우 착색되면 로퍼 옥사이드의 형성이 느려진다. 이 경우, 무색의 출발 물질을 얻기 위하여, 톨루엔 / 펜​​ 테인을 사용하여 재결정 화 또는 컬럼 크로마토 그래피로 정제. 칼럼 크로마토 그래피에 의한 정제를 위해, 실리카 겔의 하층과 알루미나의 상층과 열을 포장한다. 칼럼의 상단에 tetrahydrocarbazole을 넣고 톨루엔으로 용출. 모든 원?...

<ol>
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요약하면, 우리는 tetrahydrocarbazoles의 CH 결합 편리 두 단계 절차에서 CN-커플 링 제품을 생성하도록 작용 될 수 있음을 입증 있었다. 첫 번째 단계는 퍼옥이주는 tetrahydrocarbazole (1) 또는 산소 원자 (17, 19)와 그 유도체의 공지 photocatalyzed 산화이다. 톨루엔에서 수행하는 경우, 하이드 로퍼 옥사이드 제품이 침전 및 여과에 의해 편리하게 단리 할 수...

CH 결합의 직접적인 작용은 유기 화학 1에서 중요하고 오랜 목표입니다. 이러한 변환은 그룹을 활성화 또는 지시의 도입 및 제거를 요구하는 기존의 방법에 비해 단계, 시간과 물질을 저장하여 합성을 간소화하기 위해 매우 강력한 될 수 있습니다. 따라서, CH 결합의 작용은 또한 녹색 화학 2의 매력입니다. 산화 조건, 두 개의 CH 결합 또는 하나 CH 하나의 헤테로 원자-H 결합에서 각각 CC와 C-헤테로 원자 결합, (그림 1) 3-9로 변환 할 수 있습니다. 종종 이러한 산화 커플 링 반응은 합성 산화 방지제, 고가의 촉매 또는 높은 온도를 필요로한다. 따라서, 많은 시도는 터미널 산화제 10으로 저렴한 촉매, 양성 조건과 산소 또는 공기를 사용하는 방법을 개발하기 위해 만들어집니다. <img alt="그림 1" fo:content-width = &quot;5 인치&quot;SRC = &quot;/ files/ftp_upload/51504/51504fig1highres.jpg&quot;폭 = &quot;500&quot;/&gt; 그림 1. 산화 커플 링 반응. <a href="https://www.jove.com/files/ftp_upload/51504/51504fig1highres.jpg" target="_blank">이 그림의 더 큰 버전을 보려면 여기를 클릭하십시오.</a> 많은 유기 화합물은 효과적으로 로퍼 옥사이드 부분 (11, 12)를 형성하는 O 2를 삽입하여 CH 결합을 기능화 수 자동 산화 반응에서 공기로부터 산소와 느리게 반응한다. 자동 산화 공정은 탄화수소 공급 원료에서 생성되는 산소 화합물 산업 규모에 사용하지만, 자동 산화는 가치있는 화합물 또는 물질의 분해에 이르게하는 경우도 원치 않는 과정이다됩니다. 어떤 경우에는, 예를 들어 디 에틸 에테르에 대해, 공기 형성 로퍼 또한 폭발성 일 수있다. 최근에, 우리는 산화 - 환원 활성 촉매 (13, 14)의 필요없이 CH 결합에서 새로운 CC 결합을 형성 할 수있는 자동 산화를 활용하는 반응을 발견 </SUP&gt;. 단순히 산 촉매의 존재하에 산소의 기판을 교반하는 새로운 제품의 형성에 이르게한다. 반응의 핵심은 산 촉매 (15)에 의해 제 2 기판으로 대체하는 중간 하이드 로퍼 옥사이드의 손쉬운 형성이다. 반응은, 그러나, 크 산텐하도록 제한하고 쉽게 산소 및 제품의 분위기 하에서 산화 몇 관련 화합물은 지금까지 발견되지 어플리케이션을 가지고있다. 그럼에도 불구하고이 발견에 의해 영감을, 우리는 약학 적 활성 인돌 유도체 (16)를 합성하는 중간 과산화물 (칩)을 통해 CH의 작용의 원리를 활용하여 관련 산화 커플 링 방법을 개발했다. 인돌, 특히 1 tetrahydrocarbazoles 쉽게 증감 제 및 가시광 (20)를 사용하여 생성 될 수있는 일 중항 산소 17-19의 존재하에 하이드 로퍼 옥사이드를이 산화 될 수있다. 유압operoxide 부분 할 수있는 산 촉매에 의해 활성화 및 친핵체 (21, 22)의 도입을 허용하는 경우 이탈 기로서 원칙적으로 행동합니다. 과산화수소는 쿠멘, 호크 과정 (23)로부터 페놀의 산업 합성에 이용으로 산 재 배열 반응을 촉매 받아야하는 것으로 알려져있다. 주의 최적화 연구에 의해, 우리는 재 배열 (16)에 의해 원치 않는 분해 경로를 통해 아닐린 3와 같은 N-친핵체를 사용하여 원하는 치환 반응을 선호하는 조건을 찾아 낼 수 있었다. 여기에서, 우리는 가시 광선, 과민성, 산소와 산을 사용, 구체적으로이 두 단계 CHIPS 절차를 설명합니다. 선택한 제품은 높은 항 바이러스 활성을 나타내거나 종양 치료 24-26에 중요 할 수있다 혈관 내피 성장 인자 (VGF)을 억제하는 인돌 유도체 4입니다 사이.

<table border="0" cellpadding="0" cellspacing="0" width="797">
	<tbody>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">1,2,3,4-Tetrahydrocarbazole</td>
			<td style="width:139px;">Sigma Aldrich</td>
			<td style="width:151px;">T12408</td>
			<td style="width:291px;">If coloured, purification may be necessary. See Protocol 1.1</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">Methanol</td>
			<td style="width:139px;">Sigma Aldrich</td>
			<td>322415</td>
			<td>99.8% purity</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;">4-Nitroaniline</td>
			<td style="width:139px;">Acros Organics</td>
			<td>128371000</td>
			<td>99% purity</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">Trifluoroacetic acid</td>
			<td style="width:139px;">Sigma Aldrich</td>
			<td>T6508</td>
			<td>99% purity</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">Acetic acid</td>
			<td style="width:139px;">J. T. Baker</td>
			<td style="width:151px;">JTB RS 426960101</td>
			<td>99-100% purity</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">Aniline</td>
			<td style="width:139px;">Merck</td>
			<td>8222560100</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">4-Aminobenzonitrile</td>
			<td style="width:139px;">Sigma Aldrich</td>
			<td>147753</td>
			<td>98% purity</td>
		</tr>
	</tbody>
</table>

synthesis of antiviral tetrahydrocarbazole derivatives by photochemical and acid-catalyzed c-h functionalization via intermediate peroxides (chips)

The direct functionalization of C-H bonds is an important and long standing goal in organic chemistry. Such transformations can be very powerful in order to streamline synthesis by saving steps, time and material compared to conventional methods that require the introduction and removal of activating or directing groups. Therefore, the functionalization of C-H bonds is also attractive for green chemistry. Under oxidative conditions, two C-H bonds or one C-H and one heteroatom-H bond can be transformed to C-C and C-heteroatom bonds, respectively. Often these oxidative coupling reactions require synthetic oxidants, expensive catalysts or high temperatures. Here, we describe a two-step procedure to functionalize indole derivatives, more specifically tetrahydrocarbazoles, by C-H amination using only elemental oxygen as oxidant. The reaction uses the principle of C-H functionalization via Intermediate PeroxideS (CHIPS). In the first step, a hydroperoxide is generated oxidatively using visible light, a photosensitizer and elemental oxygen. In the second step, the N-nucleophile, an aniline, is introduced by Br&#248;nsted-acid catalyzed activation of the hydroperoxide leaving group. The products of the first and second step often precipitate and can be conveniently filtered off. The synthesis of a biologically active compound is shown.

1 - (5 - nitroindolin -1 - 일) -2,3,4,9 - 테트라 하이드로-1H-카바 졸 (4A) 방법 A, R의 F = 0.63 (헥산 / 에틸 아세테이트 70:30)에 따라 합성. 정제 : 방법 A, 워크 업 변이체 A1을 사용하여 생성물을 정제는 (2.4, 2.5, 2.6 단계). 오렌지색 고체, 수율 : 95 %. 1 H NMR (500 MHz 이상, DMSO-D6) : <em...

Watch this Scientific Journal Video about Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS at JoVE.com

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

중간 과산화물을 통해 광화학 및 산 - 촉매 CH 기능화에 의한 항 바이러스 Tetrahydrocarbazole 유도체의 합성 (CHIPS)

A two-step procedure for the synthesis of pharmaceutically active indole-derivatives by C-H functionalization with anilines is described, using photo- and Br&#248;nsted acid catalysis.

The direct functionalization of C-H bonds is an important and long standing goal in organic chemistry. Such transformations can be very powerful in order ...

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Unit 1

Acids and Bases

SCIENTISTS IN ACTION

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