Name: preparation of n-(2-alkoxyvinyl)sulfonamides from n-tosyl-1,2,3-triazoles and subsequent conversion to substituted phthalans and phenethylamines
Uploaded: 2018-01-03T15:00:00
Description: Watch this Scientific Journal Video about Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines at JoVE.com

这项工作由汉密尔顿学院和爱德华和弗吉尼亚泰勒基金资助, 用于学生/教员的化学研究。

1. 合成n-磺唑 2a: (2-(1-磺-1H-12, 3-唑-4-基) 苯基) 甲醇
<ol>
	<li>添加一个 3 x 10 mm 聚四氟乙烯磁性搅拌棒, 139 毫克 2 ethynylbenzyl 酒精, 和20毫克的铜 (I) 吩 (CuTC) 的烤箱干 2-5 毫升微波瓶和密封瓶安全与隔膜帽和机。由于微波的快速加热, 总是使用新的小瓶和无任何缺陷的瓶盖, 并确保瓶盖是安全和适当的安装。</li>
	<li>真空下从瓶子中取出空气, 再用氩气充三次。</li>
	<li>通过注射器加入4毫?...

<ol>
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Lett. 18 (21), 5500-5503 (2016).</li><li>Yu, Y., Zhu, L., Liao, Y., Mao, Z., Huang, X. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Rhodium(II)-Catalysed+Skeletal+Rearrangement+of+Ether+Tethered+N-Sulfonyl+1,2,3-Triazoles:+a+Rapid+Approach+to+2-Aminoindanone+and+Dihydroisoquinoline+Derivatives.">Rhodium(II)-Catalysed Skeletal Rearrangement of Ether Tethered N-Sulfonyl 1,2,3-Triazoles: a Rapid Approach to 2-Aminoindanone and Dihydroisoquinoline Derivatives.</a> Adv. Synth. Catal. 358 (7), 1059-1064 (2016).</li><li>Sun, R., Jiang, Y., Tang, X. -. Y., Shi, M. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=RhII-Catalyzed+Cyclization+of+Ester/Thioester-Containing+N-Sulfonyl-1,2,3-triazoles:+Facile+Synthesis+of+Alkylidenephthalans+and+Alkylidenethiophthalans.">RhII-Catalyzed Cyclization of Ester/Thioester-Containing N-Sulfonyl-1,2,3-triazoles: Facile Synthesis of Alkylidenephthalans and Alkylidenethiophthalans.</a> Asian J. Org. Chem. 6 (1), 83-87 (2017).</li><li>Miura, T., Tanaka, T., Biyajima, T., Yada, A., Murakami, M. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=One-Pot+Procedure+for+the+Introduction+of+Three+Different+Bonds+onto+Terminal+Alkynes+through+N-Sulfonyl-1,2,3-Triazole+Intermediates.">One-Pot Procedure for the Introduction of Three Different Bonds onto Terminal Alkynes through N-Sulfonyl-1,2,3-Triazole Intermediates.</a> Angew. Chem. 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P. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Synthesis+of+2,5-epoxy-1,4-benzoxazepines+via+rhodium(II)-catalyzed+reaction+of+1-tosyl-1,2,3-triazoles+and+salicylaldehydes.">Synthesis of 2,5-epoxy-1,4-benzoxazepines via rhodium(II)-catalyzed reaction of 1-tosyl-1,2,3-triazoles and salicylaldehydes.</a> Tetrahedron. 72 (1), 176-183 (2016).</li><li>Cheng, X., Yu, Y., Mao, Z., Chen, J., Huang, X. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Facile+synthesis+of+substituted+3-aminofurans+through+a+tandem+reaction+of+N-sulfonyl-1,2,3-triazoles+with+propargyl+alcohols.">Facile synthesis of substituted 3-aminofurans through a tandem reaction of N-sulfonyl-1,2,3-triazoles with propargyl alcohols.</a> Org. Biomol. Chem. 14 (16), 3878-3882 (2016).</li><li>Mi, P., Kumar, R. 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三2 a-b可以通过铜 (I)-催化叠氮化-炔烃 [3 + 2] 加 (CuAAC) 以 CuTC 为催化剂清洁地获得。值得注意的是, 在高温下, 三唑2a是最有效的, 通过标准氯仿回流在3h 或加热到100° c, 在微波反应器中15分钟 (注: 时间可能因微波效率的不同而变化);然而, 三唑2b通过室温下的 CuAAC 最有效地制备。因此, 在新的基板上执行本协议时, 必须努力确定此基板相关反应的最佳条件。在微?...

铑 (II)-azavinyl carbenoids 最近出现了作为一个异常地多才多艺的反应中间 en 到许多可贵的产品的路线。1,2,3,4,5,6,7,8,9,10特别地, 这些中间体的许多新颖的用途为生产杂10为化学家提供了新的和高效率的综合战略。为此, 我们集团发起了一项新的 phthalans11合成协议的开发, 这将利用最近在和 oxygen-based 核内分子内添加的进展到 Rh (II)-azavinyl carbenoids从N-sulfonyl-1,2,3-triazoles 派生的。12,13,14,15,16,17我们的方法具有一个简单的 two-step 协议, 用于将终端炔烃如1转换为N-sulfonyl-1,2,3-triazoles 2 , 并带有一个下垂的酒精 (图 1)。随后, Rh (II)-催化脱/13 OH 插入级联从2提供 phthalans 3具有反应性的N(2-alkoxyvinyl) 磺胺类官能团。
由于n-(2-alkoxyvinyl) 磺胺类基团是一种潜在的多用途, 但相对 (的n-和O-包含 synthon,16,17,18,19,20,21,22,23,24,25,26,27在各种条件下 (图 2), 我们对其熔融烯-醚/烯-磺酰胺系统的反应性感兴趣。在筛选各种还原协议后, 确定了两种方法, 它们导致了稳定的 phthalan 和/或包含乙胺的产品 (图 2, 3 → 4/5)。首先, 它被发现, 标准氢化的N-(2-alkoxyvinyl) 磺酰胺的3a与催化钯碳 (Pd/c) 有选择地减少 c = c 键屈服 phthalan 4。另外, 在乙醚/甲苯中使用钠双 (2-氧) 铝氢化物处理的3a提供了唯一替代的乙胺导数5。我们认为, 这两种转换都是有价值的, 因为它们导致具有潜在生物活性的产品类别, 包括嵌入乙胺产生的活性属性, 而在4的情况下, 金属螯合通过面向cis的N和O-原子。
在调查酸性促进的添加物以利用富含电子的 c = c 键的3a时, 发现在酒精或硫醇存在的情况下, 用催化的三甲基硅基氯化物处理此化合物, 产生了酮6 c和分别 thioketal 6e, 同时保持双 phthalan 框架的完整性。另外, 在1:1 乙酸/水溶液中搅拌3a会产生稳定的 hemiketal 6d。

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			<td height="21" style="height:21px;width:324px;">2-Ethynylbenzyl alcohol, 95%</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">520039</td>
			<td style="width:167px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Copper (I) thiophene-2-carboxylate</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">682500</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Chloroform, &#8805;99%</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">372978</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Toluenesulfonylazide, 99.24%</td>
			<td style="width:219px;">Chem-Impex International</td>
			<td style="width:119px;">26107</td>
			<td>Potentially explosive</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Dichloromethane, &#8805;99.5%</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">320269</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Rhodium (II) acetate dimer, 99%</td>
			<td style="width:219px;">Strem Chemicals</td>
			<td style="width:119px;">45-1730</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Silica Gel, 32-63, 60A</td>
			<td style="width:219px;">MP Biomedicals Inc.</td>
			<td style="width:119px;">2826</td>
			<td>For silica gel plugs</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Hexanes</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">178918</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Ethyl acetate</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">439169</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Chlorofom-D</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">151823</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Ethylene glycol</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">293237</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Chlorotrimethylsilane, 98%</td>
			<td style="width:219px;">Acros</td>
			<td style="width:119px;">11012</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Sodium bicarbonate</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">S6014</td>
			<td>Dissolved in deionized water to prepare a saturated aqueous solution</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Sodium sulfate</td>
			<td style="width:219px;">Fisher Scientific</td>
			<td style="width:119px;">S429</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Ethyl alcohol, absolute - 200 proof</td>
			<td style="width:219px;">Aaper Alcohol and Chemical Co.</td>
			<td style="width:119px;">82304</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">10 wt% Palladium on carbon</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">520888</td>
			<td>Can ignite in the presence of air, hydrogen gas, and/or a flammable solvent</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Hydrogen gas</td>
			<td style="width:219px;">Praxair</td>
			<td style="width:119px;">UN1049</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Diethyl ether</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">309966</td>
			<td></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:324px;">60 wt% sodium bis(2-methoxyethoxy)aluminum hydride solution in toluene</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">196193</td>
			<td>Reacts violently with water</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Methanol</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">34966</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Ammonium chloride</td>
			<td style="width:219px;">Fisher Scientific</td>
			<td style="width:119px;">A661</td>
			<td>Dissolved in deionized water to prepare a saturated aqueous solution</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Hydrochloric acid, 37%</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">258148</td>
			<td>Dissolved in deionized water to prepare a 1M solution</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Sodium Chloride</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">S25541</td>
			<td>Dissolved in deionized water to prepare a saturated aqueous solution</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">2-5 mL Microwave vials</td>
			<td style="width:219px;">Biotage</td>
			<td style="width:119px;">355630</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Microwave vial caps</td>
			<td style="width:219px;">Biotage</td>
			<td style="width:119px;">352298</td>
			<td></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:324px;">RediSep Rf Gold Normal Phase, Silica Columns, 20 &#8211; 40 micron</td>
			<td style="width:219px;">Teledyne Isco</td>
			<td style="width:119px;">69-2203-345</td>
			<td>For column chromatography</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Balloons</td>
			<td style="width:219px;">CTI Industries Corp.</td>
			<td style="width:119px;">912100</td>
			<td>For hydrogenation</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Biotage Initiator+ Microwave Reactor</td>
			<td style="width:219px;">Biotage</td>
			<td style="width:119px;">356007</td>
			<td></td>
		</tr>
	</tbody>
</table>

preparation of n-(2-alkoxyvinyl)sulfonamides from n-tosyl-1,2,3-triazoles and subsequent conversion to substituted phthalans and phenethylamines

分解的N-tosyl-1,2,3-triazoles 与铑 (II) 乙酸二聚体在醇的存在形式综合地多才多艺的N-(2-alkoxyvinyl) 磺胺, 在各种各样的情况下起反应到负担得起有用的n和包含化合物的O。酸催化添加醇或硫到N-(2-alkoxyvinyl) 含有磺胺类的 phthalans, 分别提供了酮和 thioketals 的通道。选择性还原乙烯基在N-(2-alkoxyvinyl) 含有磺酰胺的 phthalans 通过加氢生成相应的 phthalan 在良好的产量, 而减少与钠双 (2-氧) aluminumhydride 产生环形开启的乙胺模拟。由于N-(2-alkoxyvinyl) 磺酰胺官能团是综合通用的, 但通常作用不稳定, 因此该协议强调在准备、处理和反应这些关键基板的几个有用转换.

本研究的所有化合物都以1H 和13C 核磁共振波谱和电喷雾质谱 (ESI) 为特征, 以确认产品结构并评估纯度。本节描述了代表性化合物的关键数据。
光谱数据与2a (图 3) 的三唑结构有很好的一致性。在2a的1H 核磁共振谱中, 三唑的特征 C5 质子出现在 8.45 ppm, 为1H ...

Watch this Scientific Journal Video about Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines at JoVE.com

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

准备n-(2-alkoxyvinyl) 磺胺从n-tosyl-1,2,3-triazoles 和随后转换为取代 Phthalans 和 Phenethylamines

本文详细介绍了合成N-(2-alkoxyvinyl) 磺胺以及随后转换为 phthalan 和乙胺衍生物的典型实验过程。

Decomposition of N-tosyl-1,2,3-triazoles with rhodium(II) acetate dimer in the presence of alcohols forms synthetically versatile ...

Research

Education

JoVE Core

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Organic Chemistry

Chemistry

Unit 1

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Amines

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