One-pot sequential diprop-2-ynylation and cycloaddition: An efficient synthesis of novel N,N-bis(1,2,3-triazol-4-yl) methylarylamines starting from primary amines

Zhu-Jun He; Mei-Hong Wei; Xiao-Lan Zhang; Jun-Min Chen; Shou-Ri Sheng

首页> 外文期刊>Synthetic Communications >One-pot sequential diprop-2-ynylation and cycloaddition: An efficient synthesis of novel N,N-bis(1,2,3-triazol-4-yl) methylarylamines starting from primary amines

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One-pot sequential diprop-2-ynylation and cycloaddition: An efficient synthesis of novel N,N-bis(1,2,3-triazol-4-yl) methylarylamines starting from primary amines

机译：单壶顺序DiProp-2-ynylation和环加成：从原发性胺开始的新型N，N-BIS（1,2,3-三唑-4-基）的高效合成甲基芳基胺

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摘要

A facile, one-pot synthesis strategy for the tertiary arylamines bearing N,N-bis(1,2,3-triazol-4-yl)methyl structure has been developed by sequential diprop-2-ynylation of primary amines with propargyl bromide in the presence of calcium hydride in DMF and [3+2] “click” cycloaddition with organic azides promoted by cupric acetate in the mixed DMF-H_2O media. This protocol provides some features, such as high efficiency and regioselectivity, easy operation, and moderate to good product yield (56-84%) with a wide substrate scope under mild conditions.

机译：用于轴承N，N-BIS（1,2,3-三唑-4-基）甲基结构的亚芳基胺的容纳，一锅合成策略已经通过母胺与丙基溴IN的顺序DiPROP-2-炔胺开发在DMF和[3 + 2]中的氢化钙在混合DMF-H_2O培养基中通过醋酸铜衍生促进的有机叠氮。该方案提供了一些特征，例如高效率和地区选择性，易于操作，并且在温和条件下具有宽的基板范围的良好产品产量（56-84％）。

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来源
《Synthetic Communications》 |2019年第20期|共7页
作者
Zhu-Jun He; Mei-Hong Wei; Xiao-Lan Zhang; Jun-Min Chen; Shou-Ri Sheng;
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作者单位

Key Laboratory of Functional Small Organic Molecule Ministry of Education Jiangxi Normal University Nanchang People’s Republic of China;

Key Laboratory of Functional Small Organic Molecule Ministry of Education Jiangxi Normal University Nanchang People’s Republic of China;

Key Laboratory of Functional Small Organic Molecule Ministry of Education Jiangxi Normal University Nanchang People’s Republic of China;

Key Laboratory of Functional Small Organic Molecule Ministry of Education Jiangxi Normal University Nanchang People’s Republic of China;

Key Laboratory of Functional Small Organic Molecule Ministry of Education Jiangxi Normal University Nanchang People’s Republic of China;

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原文格式 PDF
正文语种 eng
中图分类有机化学;
关键词
Cycloaddition; diprop-2-ynylation; N; N-bis(1; 2; 3-triazol-4-yl) methylarylamines; one-pot procedure;

机译：环加成;DiProp-2- ynylation;N;N-BIS（1;2;3-三唑-4-基）甲基芳基胺;单盆手术;

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专利

1. One-pot sequential diprop-2-ynylation and cycloaddition: An efficient synthesis of novel N,N-bis(1,2,3-triazol-4-yl) methylarylamines starting from primary amines [J] . Zhu-Jun He, Mei-Hong Wei, Xiao-Lan Zhang, Synthetic Communications . 2019,第17a20期

机译：单壶顺序DiProp-2-ynylation和环加成：从原发性胺开始的新型N，N-BIS（1,2,3-三唑-4-基）的高效合成甲基芳基胺
2. One-pot synthesis of novel N,N-bis(isoxazol-5-yl)methyl tertiary arylamines via sequential diprop-3-ynylation and 1,3-dipolar cycloaddition from primary amines [J] . Zhang Xiao-Lan, Wei Mei-Hong, Sheng Shou-Ri, Journal of chemical research: reviews and research papers from all branches of chemistry . 2019,第9a10期

机译：通过顺序DiPROP-3-ynylation和1,3-偶极环加入的新型N，N-BIS（异恶唑-5-基）甲基叔芳基的单壶合成伯胺
3. ONE-POT SYNTHESIS OF NOVEL (2-OXO-1,2-DIHYDROPYRIDIN-3-YL)-1,3,5-TRIAZINE DERIVATIVES FROM METHYL 2-(N-TRIPHENYLPHOSPHORANYLIDENE)AMINONICOTINATE ARYL ISOCYANATES AND PRIMARY AMINES - SEQUENTIAL AZA-WITTIG/CYCLOADDITION/RING-TRANSFORMATION REACTIONS [J] . Okawa T., Eguchi S., Kakehi A., Tetrahedron . 1997,第47期

机译：一锅合成甲基（2-氧-1,2-二羟基吡啶-3-基）-1,3,5-三嗪衍生物的甲基2-（N-对苯二膦烯）氨基壬酸酯异氰酸酯和初级酰胺-顺序的氮杂氮杂WITTIG /循环载荷/环转变反应
4. Highly Efficient Organic and Macromolecular Synthesis Using Sequential Copper Catalyzed Azide-Alkyne 3+2 Cycloaddition and ATRA/ATRP [C] . Carolynne L. Ricardo, Tomislav Pintauer American Chemical Society symposium on controlled/living radical polymerization . 2012

机译：连续铜催化叠氮化物-炔烃3 + 2环加成反应和ATRA / ATRP的高效有机和大分子合成
5. I. Synthesis of N,N-bis(3-butenyl)amines from (2-azaallyl)nitriles. II. Synthesis of highly substituted pyrrolizidines from cyclic carbinol amides. III. Synthesis of potential phototriggered DNA crosslinking agents. [D] . Dietz, Amber L. 2005

机译：I.由（2-氮杂烯丙基）腈合成N，N-双（3-丁烯基）胺。二。由环状甲醇酰胺合成高度取代的吡咯烷核苷。三，潜在的光触发DNA交联剂的合成。
6. Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles [O] . Kuppusamy Bharathimohan, Thanasekaran Ponpandian, A Jafar Ahamed, 2014

机译：顺序脱羧叠氮-炔环加成和脱氢偶联反应：多锅稠合三唑的一锅合成
7. Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide [O] . Johansson, Johan R., Lincoln, Per, Nordén, Bengt, 2011

机译：伯烷基卤化物和叠氮化钠顺序一锅钌催化的叠氮化物-炔烃环加成反应
8. Use of Nitrone Cycloadditions in the Synthesis of Beta-Amino Aldehydes and Unsaturated Amines [R] . Lander, S. W. 1986

机译：硝酮环加成反应在β-氨基醛和不饱和胺合成中的应用

One-pot sequential diprop-2-ynylation and cycloaddition: An efficient synthesis of novel N,N-bis(1,2,3-triazol-4-yl) methylarylamines starting from primary amines

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