One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

被引：32

作者：

Ladouceur, Sebastien ^{[1
]}

Soliman, Ahmed M. ^{[1
]}

Zysman-Colman, Eli ^{[1
]}

机构：

[1] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada

来源：

SYNTHESIS-STUTTGART | 2011年 / 22期

基金：

加拿大自然科学与工程研究理事会;

关键词：

click chemistry; Huisgen cycloaddition; triazoles; alkynes; azides; RHENIUM TRICARBONYL COMPLEXES; SITU GENERATED AZIDES; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; TERMINAL ALKYNES; 1,3-DIPOLAR CYCLOADDITIONS; REGIOSELECTIVE SYNTHESIS; RUTHENIUM(II) COMPLEXES; IRIDIUM(III) COMPLEXES; COUPLING REACTION; LIGANDS;

D O I：

10.1055/s-0030-1260256

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.

引用

页码：3604 / 3611

页数：8

共 50 条

[21] An Efficient, One-Pot, Regioselective Synthesis of 1,4-Diaryl-1H-1,2,3-triazoles Using Click Chemistry
Kumar, Dalip
Reddy, Vaddula Buchi
SYNTHESIS-STUTTGART, 2010, (10): : 1687 - 1691
[22] One-pot multistep synthesis of 1-fluoroalkylisoquinolines and fused fluoroalkylpyridines from N-fluoroalkyl-1,2,3-triazoles
Kubickova, Anna
Voltrova, Svatava
Kleman, Adam
Klepetarova, Blanka
Beier, Petr
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (16): : 4442 - 4448
[23] One-pot chemoenzymatic synthesis of chiral disubstituted 1,2,3-triazoles in aqueous media
de Oliveira, Camila de Souza
de Andrade, Kleber Tellini
Omori, Alvaro Takeo
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 91 : 93 - 97
[24] From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles
Huang, Kai
Sheng, Guorong
Lu, Ping
Wang, Yanguang
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10): : 5294 - 5300
[25] Recyclable clay supported Cu (II) catalyzed tandem one-pot synthesis of 1-aryl-1,2,3-triazoles
Mohammed, Shabber
Padala, Anil K.
Dar, Bashir A.
Singh, Baldev
Sreedhar, B.
Vishwakarma, Ram A.
Bharate, Sandip B.
TETRAHEDRON, 2012, 68 (39) : 8156 - 8162
[26] Mass Spectrometric Characterization of N-Alkyl-4-nitro-1,2,3-triazoles
Sukhanov, G. T.
Bosov, K. K.
Filippova, YU. V.
Sukhanova, A. G.
Krupnova, I. A.
Pivovarova, E. V.
CHEMISTRY FOR SUSTAINABLE DEVELOPMENT, 2022, 30 (06): : 676 - 685
[27] Copper(I)-Catalyzed Interrupted Click/Sulfenylation Cascade: One-Pot Synthesis of Sulfur Cycle Fused 1,2,3-Triazoles
Wang, Weiguo
Huang, Shuai
Yan, Shikun
Sun, Xuejun
Tung, Chen-Ho
Xu, Zhenghu
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (05) : 445 - 448
[28] One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides
Feldman, AK
Colasson, B
Fokin, VV
ORGANIC LETTERS, 2004, 6 (22) : 3897 - 3899
[29] Click chemistry inspired one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their Src kinase inhibitory activity
Kumar, Dalip
Reddy, V. Buchi
Kumar, Anil
Mandal, Deendayal
Tiwari, Rakesh
Parang, Keykavous
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (01) : 449 - 452
[30] THE STRUCTURE OF QUATERNARY SALTS FROM 1-ALKYL-1,2,3-TRIAZOLES
WILEY, RH
MOFFAT, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (06) : 1703 - 1704

← 1 2 3 4 5 →