I2/NaH2PO2-mediated deoxyamination of cyclic ethers for the synthesis of N-aryl-substituted azacycles

被引：2

作者：

Lin, Ying ^{[1
]}

Li, Dongyang ^{[1
]}

Zhang, Jingjing ^{[1
]}

Tang, Zhi ^{[1
]}

Liu, Long ^{[1
]}

Huang, Tianzeng ^{[1
]}

Li, Chunya ^{[1
]}

Chen, Tieqiao ^{[1
]}

机构：

[1] Hainan Univ, Hainan Prov Fine Chem Engn Res Ctr, Key Lab Minist Educ Adv Mat Trop Isl Resources, Hainan Prov Key Lab Fine Chem, Haikou 570228, Hainan, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2021年 / 45卷 / 45期

关键词：

AROMATIC-AMINES; PYRROLIDINE; EFFICIENT; TETRACARBONYLHYDRIDOFERRATE; HETEROCYCLIZATION; DERIVATIVES; PIPERIDINE; AMINATION; ARYLATION; CATALYST;

D O I：

10.1039/d1nj04752c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a protocol for efficient synthesis of N-aryl-substituted azacycles from aryl amines and cyclic ethers using I-2/NaH2PO2 as the mediator. A diverse range of aryl amines and cyclic ethers undergo amination reaction to generate products in good to excellent yields with good functional group tolerance. This reaction can be easily scaled up to give N-aryl-substituted azacycles on a gram scale. Further chemical manipulation of the products enabled useful transformations of the quinoline ring, including bromination and acetylation.

引用

页码：21011 / 21014

页数：4

共 41 条

[1] Ruthenium-complex-catalyzed N-(cyclo)alkylation of aromatic amines with diols.: Selective synthesis of N-(ω-hydroxyalkyl)anilines of type PhNH(CH2)nOH and of some bioactive arylpiperazines [J].

Abbenhuis, RATM ;

Boersma, J ;

van Koten, G .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4282-4290

[2] THE REACTION OF TETRAHYDROPYRAN WITH PRIMARY AROMATIC AMINES OVER ACTIVATED ALUMINA [J].

BOURNS, AN ;

EMBLETON, HW ;

HANSULD, MK .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1952, 30 (01) :1-8

[3] Transition-Metal-Free O-, S-, and N-Arylation of Alcohols, Thiols, Amides, Amines, and Related Heterocycles [J].

Cano, Rafael ;

Ramon, Diego J. ;

Yus, Miguel .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02) :654-660

[4] Sustainable electrochemical cross-dehydrogenative coupling of 4-quinolones and diorganyl diselenides [J].

Chen, Jin-Yang ;

Wu, Hong-Yu ;

Gui, Qing-Wen ;

Yan, Shan-Shu ;

Deng, Jie ;

Lin, Ying-Wu ;

Cao, Zhong ;

He, Wei-Min .

CHINESE JOURNAL OF CATALYSIS, 2021, 42 (09) :1445-1450

[5] Synthesis of n-phenylpyrrolidine and n-hexahydrophenylpyrrolidine [J].

Craig, LC ;

Hixon, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1930, 52 :804-808

[6] Development of a General Non-Noble Metal Catalyst for the Benign Amination of Alcohols with Amines and Ammonia [J].

Cui, Xinjiang ;

Dai, Xingchao ;

Deng, Youquan ;

Shi, Feng .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (11) :3665-3675

[7] Cp*Ir complex-catalyzed N-heterocyclization of primary amines with diols:: A new catalytic system for environmentally benign synthesis of cyclic amines [J].

Fujita, KI ;

Fujii, T ;

Yamaguchi, R .

ORGANIC LETTERS, 2004, 6 (20) :3525-3528

[8] Molecular iodine-catalyzed multicomponent synthesis of α-cyanopyrrolines with ambient air as the oxidant under neat conditions [J].

Gui, Qing-Wen ;

Teng, Fan ;

Li, Zhou-Chao ;

Jin, Xue-Feng ;

Zhang, Mei ;

Dai, Jia-Ni ;

Lin, Ying-Wu ;

Cao, Zhong ;

He, Wei-Min .

ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (24) :4026-4030

[9] Efficient Iron-Catalyzed N-Arylation of Aryl Halides with Amines [J].

Guo, Diliang ;

Huang, He ;

Xu, Jinyi ;

Jiang, Hualiang ;

Liu, Hong .

ORGANIC LETTERS, 2008, 10 (20) :4513-4516

[10] GEM-CYCLODIALKYLATION - A FACILE SYNTHETIC ROUTE TO N-SUBSTITUTED HETEROCYCLES [J].

HARGIS, DC ;

SHUBKIN, RL .

TETRAHEDRON LETTERS, 1990, 31 (21) :2991-2994

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