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毫升无水氯仿, 开始磁搅拌。</li>
	<li>添加0.15 毫升的 p-磺叠氮化物 (tsn-3) 滴通过注射器。警告!p-磺叠氮化物可能是爆炸性的28 , 必须使用适当的个人防护设备进行处理。</li>
	<li>将密封的微波瓶在100° c 的微波反应器中加热15分钟.警告!请勿使用标准微波炉或未经授权的化学合成设备。 注: 本协议采用商用微波反应器。吸收水平设置为 "正常", 搅拌速度保持在每分钟600轮换 (RPM)。其他的用于化学合成的微波反应器也可能适用于该协议, 尽管理想的时间、温度和其他参数可能会有所不同。</li>
	<li>用压缩空气流将反应釜冷却到室温 (〜 2-3 分钟), 然后将反应混合物转移到100毫升的圆底烧瓶。用额外的 2 x 10 毫升的二氯甲烷清洗反应瓶, 将任何残留的原油转移到100毫升圆底烧瓶中。</li>
	<li>加入〜1.5 克硅胶到相同的圆形底瓶和去除溶剂使用旋转蒸发器。</li>
	<li>紧密包装硅胶吸附与粗产品成一个固体负载墨盒和附加到一个12克包装硅胶柱自动闪光色谱。 注: 本协议采用了自动净化系统、固体负载墨盒和12克硅胶柱。溶剂流动率维持在大约30毫升/分钟. 自动闪光色谱法是不需要纯化的;传统的闪光层析也可以使用。但是, 我们支持自动化, 因为它通常使人能够在发生重大分解之前尽快隔离复合2a 。</li>
	<li>运行该列使用连续梯度 0-100% 乙酸乙酯在 hexanes 超过15分钟, 开始与纯 hexanes 和结束纯乙酸乙酯。收集的主要峰值, 由紫外线吸收在 254 nm 和集中的组合, 相应的分数在一个旋转蒸发器获得纯化产品2a作为一个白色固体。 注: 三唑2a通常在氩气下以 2-5 ° c 储存 1-2 周时被发现是稳定的。但是, 某些批次的产品降解速度较快, 可能是由于来自 CDCl3的 DCl 污染。因此, 我们建议通过使用 CDCl3中和与 K2CO3并立即在随后的反应中使用它来分析产品的纯度, 从而取得最佳效果。</li>
</ol>
2. 合成N-(2-alkoxyvinyl) 磺酰胺 phthalan 3a: (Z)-N-(呋喃-1 (3H)-ylidenemethyl)-4-methylbenzenesulfonamide
<ol>
	<li>添加一个 3 x 10 mm 聚四氟乙烯磁性搅拌棒和4.6 毫克的铑 (II) 乙酸二聚体的烤箱干 0.5-2 毫升微波瓶和密封瓶安全的隔膜帽和机。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>在氩气气氛下, 在1毫升的无水氯仿中溶解152毫克的三唑2a , 然后通过注射器将得到的溶液转移到微波容器。用额外的2毫升氯仿将含有残余三唑的烧瓶冲洗两次, 并将其转移到同一微波容器中, 以确保所有起始物料都被转移。</li>
	<li>将密封的微波瓶在100° c 的微波反应器中加热 1 h.警告!请勿使用标准微波炉或未经授权的化学合成设备。 注: 本协议采用商用微波反应器。吸收水平设置为 "正常", 搅拌速度保持在每分钟600轮换 (RPM)。其他的用于化学合成的微波反应器也可能适用于该协议, 尽管理想的时间、温度和其他参数可能会有所不同。</li>
	<li>用一股压缩空气和过滤器通过短的硅胶, 用乙酸乙酯洗脱, 将反应容器冷却到室温下 (〜 2-3 分钟)。</li>
	<li>将滤液在真空中, 使用带有温暖 (〜30° c) 水浴的旋转式蒸发器, 以获得足够纯度的产品, 以便立即用于随后的反应。 
	注意产品快速分解 (在1h 以内), 如在 CDCl3中含有残余 DCl 的轻度酸性条件下, 并逐渐 (在 1-3d 以内), 当在氩下在 3-5 ° c 下储存整齐时。因此, 我们建议通过使用 CDCl3中和与 K2CO3并立即在随后的反应中使用它来分析产品的纯度, 从而取得最佳效果。</li>
	<li>如有必要, 通过用 0-75% 梯度的乙酸乙酯在 hexanes 超过15分钟, 从纯 hexanes 开始, 以75% 乙酸乙酯在 hexanes。 注: 本协议采用了自动净化系统、固体负载墨盒和12克硅胶柱。溶剂流动率维持在大约30毫升/分钟. 自动闪光色谱法是不需要纯化的;传统的闪光层析也可以使用。但是, 我们支持自动化, 因为它通常使人能够在发生重大分解之前尽快隔离复合3a 。</li>
</ol>
3。Phthalan 4 的合成: N-((13-dihydroisobenzofuran-1-基) 甲基)-4-methylbenzenesulfonamide
<ol>
	<li>在一个25毫升的圆形底瓶与磁性搅拌棒, 溶解211毫克新鲜制备的 phthalan 3a在15毫升的绝对乙醇在氩气气氛下。</li>
	<li>在碳瓶上加入149毫克的 10% 钯, 注意尽量减少暴露在空气中。警告!确保反应混合物在氩气或氮气气氛下是非常重要的。碳钯可以在空气、氢气和/或易燃溶剂的存在下点燃。佩带所有适当的个人防护设备, 并主动在附近放置一个灭火器和/或一桶沙子来扑灭火焰。</li>
	<li>用氢气把标准的乳胶气球装在注射器上。请勿超过建议的气球容量。</li>
	<li>用针头将气球和注射器连接到反应血管, 穿透隔膜。检查以确保气球和/或隔膜没有泄漏。</li>
	<li>用氢气代替氩气, 在将球囊捏出时, 在反应釜上应用微弱的真空, 然后在停止真空后, 用氢气填充容器。重复两次。</li>
	<li>搅拌24小时的反应, 然后取出气球。</li>
	<li>用氩气清洗烧瓶, 然后通过硅胶塞洗液和乙酸乙酯过滤溶液。小心丢弃含有钯的硅胶, 并将其与水混合, 放入密封的固体废物容器内。</li>
	<li>将溶剂在真空中删除以提供产品。</li>
</ol>
4. 乙胺5的合成: N-(2-(羟甲基) 苯乙基)-4-methylbenzenesulfonamide
<ol>
	<li>在一个10毫升的圆形底瓶, 溶解169毫克新鲜制备的 phthalan 3a与5毫升乙醚下的氩气气氛。</li>
	<li>冷却反应混合物到0° c 使用冰浴, 然后慢慢地增加0.52 毫升的 60% 溶液的钠双 (2-氧) 铝氢化物在甲苯。警告!二 (2-氧) 氢化钠与水发生剧烈反应。仅在无湿气、惰性的气氛中使用此试剂。</li>
	<li>室温下将反应混合物搅拌18小时。</li>
	<li>冷却反应混合物到0° c, 然后小心地加入0.5 毫升的甲醇滴超过2分钟搅拌为一个额外的2分钟, 在0° c。警告!将甲醇添加到双 (2-氧) 铝氢化物是放热的。确保解决方案足够冷, 并注意避免同时添加甲醇。</li>
	<li>在0° c 时, 加入0.6 毫升饱和水氯化铵, 除去冰浴, 在室温下搅拌5分钟。</li>
	<li>将所得到的溶液倒入含有90毫升1M 盐酸的分漏斗中, 并提取60毫升乙酸乙酯三倍的水层。</li>
	<li>用30毫升水和30毫升盐水洗涤混合的有机层, 然后在硫酸钠上烘干。</li>
	<li>使用傅书礼漏斗过滤硫酸钠, 并将滤液集中在真空中, 以获得粗乙胺产品。 注意: 通常, 该产品在这一步之后是足够纯的, 但偶尔会出现来自N的分解 (2-alkoxyvinyl) 磺胺 phthalan 3a的污染物。</li>
	<li>如有必要, 用 0-100% 梯度的乙酸乙酯在 hexanes 超过15分钟, 从纯 hexanes 开始, 以纯乙酸乙酯结束, 通过柱层析在硅胶上提纯产品。 注: 本协议采用了净化系统、固体负载盒和12克硅胶柱。溶剂流动率维持在大约30毫升/分钟. 自动闪光色谱法是不需要纯化的;传统的闪光层析也可以使用。</li>
</ol>
5. 酮6c 的合成: N-((1-(2-基)-13-dihydroisobenzofuran-1-基) 甲基)-4-methylbenzenesulfonamide
<ol>
	<li>在一个10毫升的圆底烧瓶与搅拌棒, 溶解211毫克新鲜合成 phthalan 3a在2毫升的乙二醇下空气气氛和开始搅拌。</li>
	<li>使用1毫升注射器配备18针, 增加1滴三甲基硅氯的搅拌解决方案。</li>
	<li>将橡胶隔膜放在烧瓶上, 用透气针将空气打开, 并在室温下搅拌18小时的反应混合物。</li>
	<li>将反应混合物转移到125毫升分漏斗, 用50毫升的二氯甲烷冲洗, 然后加入10毫升饱和水碳酸氢钠和40毫升去离子水。</li>
	<li>用力搅拌, 经常排气, 并将有机层分离成干净的烧瓶。每次用30毫升的二氯甲烷萃取额外的三次水层。</li>
	<li>结合有机层和干硫酸钠。</li>
	<li>用傅书礼漏斗过滤硫酸钠, 将滤液集中在旋转蒸发器上。</li>
	<li>在10毫升的二氯甲烷中溶解原油, 在混合物中加入 ~ 750 毫克的硅胶, 用旋转蒸发器除去溶剂。</li>
	<li>紧密包装硅胶吸附与粗产品成一个固体负载墨盒和附加到一个12克包装硅胶柱自动闪光色谱。 注: 本协议采用了净化系统、固体负载盒和12克硅胶柱。溶剂流动率维持在大约30毫升/分钟. 自动闪光色谱法是不需要纯化的;传统的闪光层析也可以使用。</li>
	<li>运行该列使用连续梯度 0-70% 乙酸乙酯在 hexanes 超过15分钟, 开始与纯 hexanes 和结束纯乙酸乙酯。收集的主要峰值, 由紫外线吸收在 254 nm 和集中的组合, 相应的分数在一个旋转蒸发器获得纯化产品6c作为一个白色固体。</li>
</ol>

<ol>
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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. Int. Ed. 52 (14), 3883-3886 (2013).</li><li>Medina, F., Besnard, C., Lacour, J. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=One-Step+Synthesis+of+Nitrogen-Containing+Medium-Sized+Rings+via+&#945;-Imino+Diazo+Intermediates.">One-Step Synthesis of Nitrogen-Containing Medium-Sized Rings via &#945;-Imino Diazo Intermediates.</a> Org. Lett. 16 (12), 3232-3235 (2014).</li><li>Alford, J. S., Davies, H. M. L. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Mild+Aminoacylation+of+Indoles+and+Pyrroles+through+a+Three-Component+Reaction+with+Ynol+Ethers+and+Sulfonyl+Azides.">Mild Aminoacylation of Indoles and Pyrroles through a Three-Component Reaction with Ynol Ethers and Sulfonyl Azides.</a> J. Am. Chem. Soc. 136 (29), 10266-10269 (2014).</li><li>Miura, T., Tanaka, T., Matsumoto, K., 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+Synthesis+of+2,5-Dihydropyrroles+from+Terminal+Alkynes,+Azides,+and+Propargylic+Alcohols+by+Relay+Actions+of+Copper,+Rhodium,+and+Gold.">One-Pot Synthesis of 2,5-Dihydropyrroles from Terminal Alkynes, Azides, and Propargylic Alcohols by Relay Actions of Copper, Rhodium, and Gold.</a> Chem. Eur. J. 20 (49), 16078-16082 (2014).</li><li>Jung, D. J., Jeon, J. J., Lee, J. 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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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Catal. 358 (7), 1078-1087 (2016).</li><li>Miura, T., Nakamuro, T., Kiraga, K., 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=The+stereoselective+synthesis+of+&#945;-amino+aldols+starting+from+terminal+alkynes.">The stereoselective synthesis of &#945;-amino aldols starting from terminal alkynes.</a> Chem. Commun. 50 (72), 10474-10477 (2014).</li><li>Hazen, G. G., Weinstock, L. M., Connell, R., Bollinger, F. W. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=A+Safer+Diazotransfer+Reagent.">A Safer Diazotransfer Reagent.</a> Synth. Commun. 11 (12), 947-956 (1981).</li><li>Easton, N. R., Bartron, L. R., Meinhofer, F. L., Fish, V. 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作者没有什么可透露的。

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。

<table border="0" cellpadding="0" cellspacing="0" width="829">
	<tbody>
		<tr height="21">
			<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 ...

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

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9.6K 次观看.  Hamilton College. 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。

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

Preparation and Characterization of SDF-1&#945;-Chitosan-Dextran Sulfate Nanoparticles

Chitosan (CS) and dextran sulfate (DS) are charged polysaccharides (glycans), which form polyelectrolyte complex-based nanoparticles when mixed under appropriate conditions. The glycan nanoparticles are useful carriers for protein factors, which facilitate the in vivo delivery of the proteins and sustain their retention in the targeted tissue. The glycan polyelectrolyte complexes are also ideal for protein delivery, as the incorporation is carried out in aqueous solution, which reduces the likelihood of inactivation of the proteins. Proteins with a heparin-binding site adhere to dextran sulfate readily, and are, in turn, stabilized by the binding. These particles are also less inflammatory and toxic when delivered in vivo. In the protocol described below, SDF-1&#945; (Stromal cell-derived factor-1&#945;), a stem cell homing factor, is first mixed and incubated with dextran sulfate. Chitosan is added to the mixture to form polyelectrolyte complexes, followed by zinc sulfate to stabilize the complexes with zinc bridges. The resultant SDF-1&#945;-DS-CS particles are measured for size (diameter) and surface charge (zeta potential). The amount of the incorporated SDF-1&#945; is determined, followed by measurements of its in vitro release rate and its chemotactic activity in a particle-bound form.

The objective of this protocol is to incorporate SDF-1&#945;, a stem cell homing factor, into dextran sulfate-chitosan nanoparticles. The resultant particles are measured for their size and zeta potential, as well as the content, activity, and in vitro release rate of SDF-1&#945; from the nanoparticles.

SDF-1α - 壳聚糖硫酸葡聚糖纳米粒子的制备与表征

Chitosan (CS) and dextran sulfate (DS) are charged polysaccharides (glycans), which form polyelectrolyte complex-based nanoparticles when mixed under ...

科研

化学

Preparation of Mica and Silicon Substrates for DNA Origami Analysis and Experimentation

The designed nature and controlled, one-pot synthesis of DNA origami provides exciting opportunities in many fields, particularly nanoelectronics. Many of these applications require interaction with and adhesion of DNA nanostructures to a substrate. Due to its atomically flat and easily cleaned nature, mica has been the substrate of choice for DNA origami experiments. However, the practical applications of mica are relatively limited compared to those of semiconductor substrates. For this reason, a straightforward, stable, and repeatable process for DNA origami adhesion on derivatized silicon oxide is presented here. To promote the adhesion of DNA nanostructures to silicon oxide surface, a self-assembled monolayer of 3-aminopropyltriethoxysilane (APTES) is deposited from an aqueous solution that is compatible with many photoresists. The substrate must be cleaned of all organic and metal contaminants using Radio Corporation of America (RCA) cleaning processes and the native oxide layer must be etched to ensure a flat, functionalizable surface. Cleanrooms are equipped with facilities for silicon cleaning, however many components of DNA origami buffers and solutions are often not allowed in them due to contamination concerns. This manuscript describes the set-up and protocol for in-lab, small-scale silicon cleaning for researchers who do not have access to a cleanroom or would like to incorporate processes that could cause contamination of a cleanroom CMOS clean bench. Additionally, variables for regulating coverage are discussed and how to recognize and avoid common sample preparation problems is described.

Reproducible cleaning processes for substrates used in DNA origami research are described, including bench-top RCA cleaning and derivatization of silicon oxide. Protocols for surface preparation, DNA origami deposition, drying parameters, and simple experimental set-ups are illustrated.

对于DNA折纸分析和实验准备云母和硅衬底

The designed nature and controlled, one-pot synthesis of DNA origami provides exciting opportunities in many fields, particularly nanoelectronics. Many of ...

Preparation and Characterization of Individual and Multi-drug Loaded Physically Entrapped Polymeric Micelles

Amphiphilic block copolymers like polyethyleneglycol-block-polylactic acid (PEG-b-PLA) can self-assemble into micelles above their critical micellar concentration forming hydrophobic cores surrounded by hydrophilic shells in aqueous environments. The core of these micelles can be utilized to load hydrophobic, poorly water soluble drugs like docetaxel (DTX) and everolimus (EVR). Systematic characterization of the micelle structure and drug loading capabilities are important before in vitro and in vivo studies can be conducted. The goal of the protocol described herein is to provide the necessary characterization steps to achieve standardized micellar products. DTX and EVR have intrinsic solubilities of 1.9 and 9.6 &#181;g/ml respectively Preparation of these micelles can be achieved through solvent casting which increases the aqueous solubility of DTX and EVR to 1.86 and 1.85 mg/ml, respectively. Drug stability in micelles evaluated at room temperature over 48 hr indicates that 97% or more of the drugs are retained in solution. Micelle size was assessed using dynamic light scattering and indicated that the size of these micelles was below 50 nm and depended on the molecular weight of the polymer. Drug release from the micelles was assessed using dialysis under sink conditions at pH 7.4 at 37 oC over 48 hr. Curve fitting results indicate that drug release is driven by a first order process indicating that it is diffusion driven.

The goal of this protocol is to describe the preparation and characterization of physically entrapped, poorly water soluble drugs in micellar drug delivery systems composed of amphiphilic block copolymers.

制备及个体表征和多载药物理截留聚合物胶束

Amphiphilic block copolymers like polyethyleneglycol-block-polylactic acid (PEG-b-PLA) can self-assemble into micelles above their critical micellar ...

Facile Preparation of 4-Substituted Quinazoline Derivatives

Reported in this paper is a very simple method for direct preparation of 4-substituted quinazoline derivatives from a reaction between substituted 2-aminobenzophenones and thiourea in the presence of dimethyl sulfoxide (DMSO). This is a unique complementary reaction system in which thiourea undergoes thermal decomposition to form carbodiimide and hydrogen sulfide, where the former reacts with 2-aminobenzophenone to form 4-phenylquinazolin-2(1H)-imine intermediate, whilst hydrogen sulfide reacts with DMSO to give methanethiol or other sulfur-containing molecule which then functions as a complementary reducing agent to reduce 4-phenylquinazolin-2(1H)-imine intermediate into 4-phenyl-1,2-dihydroquinazolin-2-amine. Subsequently, the elimination of ammonia from 4-phenyl-1,2-dihydroquinazolin-2-amine affords substituted quinazoline derivative. This reaction usually gives quinazoline derivative as a single product arising from 2-aminobenzophenone as monitored by GC/MS analysis, along with small amount of sulfur-containing molecules such as dimethyl disulfide, dimethyl trisulfide, etc. The reaction usually completes in 4-6 hr at 160 &#186;C in small scale but may last over 24 hr when carried out in large scale. The reaction product can be easily purified by means of washing off DMSO with water followed by column chromatography or thin layer chromatography.

A protocol for facile preparation of 4-substituted quinazoline derivatives from 2-aminobenzophenones, thiourea and dimethyl sulfoxide is presented.

的4-取代喹唑啉衍生物简便制备

Reported in this paper is a very simple method for direct preparation of 4-substituted quinazoline derivatives from a reaction between substituted ...

Laboratory Production of Biofuels and Biochemicals from a Rapeseed Oil through Catalytic Cracking Conversion

The work is based on a reported study which investigates the processability of canola oil (bio-feed) in the presence of bitumen-derived heavy gas oil (HGO) for production of transportation fuels through a fluid catalytic cracking (FCC) route. Cracking experiments are performed with a fully automated reaction unit at a fixed weight hourly space velocity (WHSV) of 8 hr-1, 490-530 &#176;C, and catalyst/oil ratios of 4-12 g/g. When a feed is in contact with catalyst in the fluid-bed reactor, cracking takes place generating gaseous, liquid, and solid products. The vapor produced is condensed and collected in a liquid receiver at -15 &#176;C. The non-condensable effluent is first directed to a vessel and is sent, after homogenization, to an on-line gas chromatograph (GC) for refinery gas analysis. The coke deposited on the catalyst is determined in situ by burning the spent catalyst in air at high temperatures. Levels of CO2 are measured quantitatively via an infrared (IR) cell, and are converted to coke yield. Liquid samples in the receivers are analyzed by GC for simulated distillation to determine the amounts in different boiling ranges, i.e., IBP-221 &#176;C (gasoline), 221-343 &#176;C (light cycle oil), and 343 &#176;C+ (heavy cycle oil). Cracking of a feed containing canola oil generates water, which appears at the bottom of a liquid receiver and on its inner wall. Recovery of water on the wall is achieved through washing with methanol followed by Karl Fischer titration for water content. Basic results reported include conversion (the portion of the feed converted to gas and liquid product with a boiling point below 221 &#176;C, coke, and water, if present) and yields of dry gas (H2-C2's, CO, and CO2), liquefied petroleum gas (C3-C4), gasoline, light cycle oil, heavy cycle oil, coke, and water, if present.

This paper presents an experimental method to produce biofuels and biochemicals from canola oil mixed with a fossil-based feed in the presence of a catalyst at mild temperatures. Gaseous, liquid, and solid products from a reaction unit are quantified and characterized. Conversion and individual product yields are calculated and reported.

通过催化裂化转换从菜籽油生物燃料和生物化学实验室生产

The work is based on a reported study which investigates the processability of canola oil (bio-feed) in the presence of bitumen-derived heavy gas oil ...

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

We present herein the optimized synthesis of a triphosphenium bromide salt. Apart from being a versatile metathesis reagent, this unusually stable low-valent-phosphorus-containing compound acts as a useful P+ transfer agent. Unlike traditional methods employed to access low-coordinate phosphorus species which usually require pyrophoric phosphorus-containing precursors (white phosphorus, Tris(trimethylsilyl)phosphine, etc.), or harsh reducing agents (alkali metals, potassium graphite, etc.), the current approach does not involve pyrophoric or explosive reagents and can be done on large scales (&#62;20 g) in excellent yields by undergraduates with basic air-free synthetic training. The bromide counter ion is readily exchanged with other anions such as tetraphenyl borate (described herein) using typical salt metathesis reagents to obtain materials with desired properties and reactivities. The versatility of this P+ transfer approach is exemplified by the reactions of these triphosphenium precursors with an N-heterocyclic carbene and an anionic bisphosphine, each of which readily displace the neutral bisphosphine to give an NHC-stabilized phosphorus(I) cation and a phosphorus(I) containing zwitterion, respectively.

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

The synthesis of a triphosphenium bromide salt is described and its use as a P+ transfer agent is outlined by reactions with an N-heterocyclic carbene and an anionic bisphosphine, yielding an NHC-stabilized P(I) cation and a P(I) containing zwitterion, respectively.

制备及反应性的Triphosphenium溴化物盐:磷方便稳定来源（I）

We present herein the optimized synthesis of a triphosphenium bromide salt. Apart from being a versatile metathesis reagent, this unusually stable ...

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

The goal of the following procedure is to provide a demonstration of the one-pot conversion of a 2-azido-1-nitrate-ester to a trichloroacetimidate glycosyl donor. Following azido-nitration of a glycal, the product 2-azido-1-nitrate ester can be hydrolyzed under microwave-assisted irradiation. This transformation is usually achieved using strongly nucleophilic reagents and extended reaction times. Microwave irradiation induces hydrolysis, in the absence of reagents, with short reaction times. Following denitration, the intermediate anomeric alcohol is converted, in the same pot, to the corresponding 2-azido-1-trichloroacetimidate.

A 2-azido-1-nitrate-ester can be converted to the corresponding 2-azido-1-trichloroacetimidate in a one-pot procedure. The goal of the manuscript is to demonstrate utility of the microwave reactor in carbohydrate synthesis.

硝酸酯 Anomeric Trichloroacetimidates 的单锅微波辅助转化

The goal of the following procedure is to provide a demonstration of the one-pot conversion of a 2-azido-1-nitrate-ester to a trichloroacetimidate ...

Preparation and Characterization of C60/Graphene Hybrid Nanostructures

Physical thermal deposition in a high vacuum environment is a clean and controllable method for fabricating novel molecular nanostructures on graphene. We present methods for depositing and passively manipulating C60 molecules on rippled graphene that advance the pursuit of realizing applications involving 1D C60/graphene hybrid structures. The techniques applied in this exposition are geared towards high vacuum systems with preparation areas capable of supporting molecular deposition as well as thermal annealing of the samples. We focus on C60 deposition at low pressure using a homemade Knudsen cell connected to a scanning tunneling microscopy (STM) system. The number of molecules deposited is regulated by controlling the temperature of the Knudsen cell and the deposition time. One-dimensional (1D) C60 chain structures with widths of two to three molecules can be prepared via tuning of the experimental conditions. The surface mobility of the C60 molecules increases with annealing temperature allowing them to move within the periodic potential of the rippled graphene. Using this mechanism, it is possible to control the transition of 1D C60 chain structures to a hexagonal close packed quasi-1D stripe structure.

Preparation and Characterization of C60/Graphene Hybrid Nanostructures

Here we present a protocol for the fabrication of C60/graphene hybrid nanostructures by physical thermal evaporation. Particularly, the proper manipulation of deposition and annealing conditions allow the control over the creation of 1D and quasi 1D C60 structures on rippled graphene.

C 型60/石墨烯混合纳米结构的制备与表征

Physical thermal deposition in a high vacuum environment is a clean and controllable method for fabricating novel molecular nanostructures on graphene. We ...

The Effect of Ultraviolet Radiation on the Chemical Bath Deposition of Bis(thiourea) Cadmium Chloride Crystals and the Subsequent CdS Obtention

In this work, the effects on the preparation of bis(thiourea) cadmium chloride crystals when illuminated with ultraviolet (UV) light at a wavelength of 367 nm using the chemical bath deposition technique are studied comparatively. Two experiments are performed to make a comparison: one without UV light and the other with the aid of UV light. Both experiments are performed under equal conditions, at a temperature of 343 K and with a pH of 3.2. The precursors used are cadmium chloride (CdCl2) and thiourea [CS(NH2)2], which are dissolved in 50 mL of deionized water with an acidic pH. In this experiment, the interaction of electromagnetic radiation is sought at the moment the chemical reaction is carried out. The results demonstrate the existence of an interaction between the crystals and the UV light; the UV light assistance causes crystal growths in an acicular shape. Also, the final product obtained is cadmium sulfide and shows no evident difference when synthesized with or without the use of UV light.

The Effect of Ultraviolet Radiation on the Chemical Bath Deposition of Bisthiourea Cadmium Chloride Crystals and the Subsequent CdS Obtention

This article presents a protocol for the synthesis of bis(thiourea) cadmium chloride crystals by chemical bath deposition. Two experiments are described: one aided by ultraviolet light compared to one without ultraviolet light.

紫外辐射对双 (硫脲) 氯化镉晶体化学镀液沉积的影响及随后的 CdS 获得

In this work, the effects on the preparation of bis(thiourea) cadmium chloride crystals when illuminated with ultraviolet (UV) light at a wavelength of ...

Synthesis of In37P20(O2CR)51 Clusters and Their Conversion to InP Quantum Dots

This text presents a method for the synthesis of In37P20(O2C14H27)51 clusters and their conversion to indium phosphide quantum dots. The In37P20(O2CR)51 clusters have been observed as intermediates in the synthesis of InP quantum dots from molecular precursors (In(O2CR)3, HO2CR, and P(SiMe3)3) and may be isolated as a pure reagent for subsequent study and use as a single-source precursor. These clusters readily convert to crystalline and relatively monodisperse samples of quasi-spherical InP quantum dots when subjected to thermolysis conditions in the absence of additional precursors above 200 &#176;C. The optical properties, morphology, and structure of both the clusters and quantum dots are confirmed using UV-Vis spectroscopy, photoluminescence spectroscopy, transmission electron microscopy, and powder X-ray diffraction. The molecular symmetry of the clusters is additionally confirmed by solution-phase 31P NMR spectroscopy. This protocol demonstrates the preparation and isolation of atomically-precise InP clusters, and their reliable and scalable conversion to InP QDs.

Synthesis of In37P20O2CR51 Clusters and Their Conversion to InP Quantum Dots

A protocol for the synthesis of In37P20(O2C14H27)51 clusters and their conversion to indium phosphide quantum dots is presented.

37p20 (o2cr)51聚类中的合成及其转化为 inp 量子点

This text presents a method for the synthesis of In37P20(O2C14H27)51 clusters and their conversion to indium phosphide quantum dots. The In37P20(O2CR)51 ...