One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

Rajasekar Shanmugam; Yadagiri Dongari; Anbarasan Pazhamalai

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One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

机译：炔烃和磺酰叠氮化物对吲哚/吡咯的一锅氨基乙基化

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A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of a-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-beta-carboline and tryptoline.

机译：使用炔烃和磺酰基叠氮化物的组合作为易于获得的氨基乙基化剂，完成了用于取代各种吲哚/吡咯的一般有效的一锅氨基乙基化反应，以合成各种色胺。该反应的特征是成功地将铜催化的炔烃和叠氮化物环加成到N-磺酰基-1,2,3-三唑上，铑催化的将a-亚氨基卡宾选择性插入到吲哚的C3-H键上，并降低了生成量在一锅中使用NaCNBH3或钯催化剂将乙酰胺酰胺化为色胺类衍生物。该反应还显示出优异的官能团耐受性，并允许以良好至优异的产率合成各种取代的色胺。这种转化构成了末端炔烃的一锅形式正式的区域选择性功能化。合成的色胺的效用在二氢-β-咔啉和色氨酸的合成中得到了进一步证明。

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《Chemistry: A European journal》 |2015年第47期|共6页
作者
Rajasekar Shanmugam; Yadagiri Dongari; Anbarasan Pazhamalai;
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正文语种 eng
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aminoethylation; indoles; rhodium; triazoles; tryptamine;

机译：氨基乙基化;吲哚;铑;三唑;色胺;

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1. One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides [J] . Rajasekar Shanmugam, Yadagiri Dongari, Anbarasan Pazhamalai Chemistry: A European journal . 2015,第47期

机译：炔烃和磺酰叠氮化物对吲哚/吡咯的一锅氨基乙基化
2. Synthesis of Pyrroles from Terminal Alkynes, N?Sulfonyl Azides, and Alkenyl Alkyl Ethers through 1?Sulfonyl-1,2,3-triazoles [J] . Cheol-Eui Kim, Sangjune Park, Dahan Eom, Organic letters . 2014,第7期

机译：通过1？磺酰基-1,2,3-三唑从末端炔烃，N？磺酰基叠氮化物和烯基烷基醚合成吡咯
3. Copper-mediated reaction of zirconacyclopentadienes with azides: A one-pot three-component synthesis of multiply substituted pyrroles from one azide and two alkynes [J] . Zhou Y., Yan X., Chen C., Organometallics . 2013,第21期

机译：铜介导的氧化锆环戊二烯与叠氮化物的反应：由一个叠氮化物和两个炔烃一锅三组分合成多取代吡咯
4. Indium-Catalyzed Three Component Reaction of Alkynes,Pyrroles and Hydrosilanes:Regioselective beta-Alkylation of Pyrroles [C] . Teruhisa Tsuchimoto, Tatsuya Wagatsuma, Taku Ainoya Symposium on Organometallic Chemistry . 2007

机译：铟催化炔烃，吡咯和氢硅烷的三种组分反应：胃肠杆菌的区域选择性β-烷基化
5. New developments toward the synthesis of heterocycles and applications in green chemistry. I. A simple and essentially one-pot synthesis of N-aminated heterocycles using phase transfer catalyst (Aliquat-336). II. Synthesis of pharmaceutically important pyrrole derivatives. III. Applications in green chemistry: Surfactant-mediated environmentally friendly cleavage of aromatic esters and trans-esterification under solvent-free neutral conditions . [D] . Patel, Nitinchandra. 2005

机译：杂环合成的新进展及其在绿色化学中的应用。 I.使用相转移催化剂（Aliquat-336）简单且基本上一锅合成N-胺化的杂环。二。药学上重要的吡咯衍生物的合成。三，在绿色化学中的应用：在无溶剂的中性条件下，表面活性剂介导的环境友好的芳族酯裂解和酯交换反应。
6. Triflic acid controlled successive annelation of aromatic sulfonamides: An efficient one-pot synthesis of N-sulfonyl pyrroles indoles and carbazoles [O] . Mohammed Abid, Liliana Teixeira, Béla Török -1

机译：三氟甲磺酸控制的芳香族磺酰胺的连续成环反应：一种有效的一锅法合成N-磺酰基吡咯吲哚和咔唑
7. Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides [O] . Yu Zhao, Zitong Zhou, Man Chen, 2021

机译：来自磺酰肼，末端炔烃和磺酰肼的N-磺酰脒的铜催化的单罐合成

One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

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