Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarb onyl-N-Propargylanilines

被引：4

作者：

Arcadi, Antonio ^{[1
]}

Calcaterra, Andrea ^{[2
]}

Fabrizi, Giancarlo ^{[2
]}

Fochetti, Andrea ^{[2
]}

Goggiamani, Antonella ^{[2
]}

Iazzetti, Antonia ^{[2
]}

Marrone, Federico ^{[2
]}

Marsicano, Vincenzo ^{[1
]}

Mazzoccanti, Giulia ^{[2
]}

Serraiocco, Andrea ^{[2
]}

机构：

[1] Univ Aquila, Dipartimento Sci Fis & Chim, I-67100 Coppito, Italy

[2] Sapienza Univ Roma, Dipartimento Eccellenza 2018 2022, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy

来源：

MOLECULES | 2021年 / 26卷 / 11期

关键词：

gold catalysis; intramolecular hydroarylation; 1,2-dihydroquinolines; QUINOLINE DERIVATIVES; CHROMENES; PLATINUM; ALKYNES;

D O I：

10.3390/molecules26113366

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the-6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-meta-substituted anilines, the regiodivergent cyclization at the ortho-/para position is achieved by the means of catalyst fine tuning.

引用

页数：13

共 7 条

[1] Synthesis of substituted 1,2-dihydroquinolines and quinolines from aromatic amines and alkynes by gold(I)-Catalyzed tandem hydroamination-hydroarylation under microwave-assisted conditions
Liu, Xin-Yuan
Ding, Pan
Huang, Jie-Sheng
Che, Chi-Ming
ORGANIC LETTERS, 2007, 9 (14) : 2645 - 2648
[2] An efficient synthesis of 4-bromo-N-substituted oxindoles by an intramolecular copper-catalyzed amidation reaction
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[3] Gold-Catalyzed Multicomponent Reaction: Facile Strategy for the Synthesis of N-Substituted 1,4-Dihydropyridines by Using Activated Alkynes, Aldehydes, and Methanamine
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[4] Gold-Catalyzed Intramolecular Hydroarylation and Transfer Hydrogenation of N-Aryl Propargylamines to Construct Tetrahydroquinolines and 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolines
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[5] N-Heterocyclic Carbene-Catalyzed Kinetic Resolution of 3-Nitro-1,2-Dihydroquinolines: Asymmetric Synthesis of All C2-, C3- and C4-Functionalized Tetrahydroquinolines
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[6] Ferric Chloride-Catalyzed Reaction of [60]Fullerene with tert-Butyl N-Substituted Carbamates: Synthesis of Oxazolidino[4,5:1,2][60]fullerenes
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JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01): : 117 - 121
[7] CuI-catalyzed synthesis of multisubstituted pyrido[1,2-a]pyrimidin-4-ones through tandem Ullmann-type C-N cross-coupling and intramolecular amidation reaction
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