Cu/Pd-Catalyzed One-Pot Synthesis of 2-(1,2,3-Triazolyl)methyl-3-alkynylImidazo[1,2-a]pyridines Involving Sequential SN Reaction/[3+2] Cycloaddition/Sonogashira Coupling Reactions

被引:1
作者
El Qami, Abdelkarim [1 ,2 ]
Jismy, Badr [1 ]
El Hakmaoui, Ahmed [2 ]
Akssira, Mohamed [2 ]
Abarbri, Mohamed [1 ]
机构
[1] Univ Tours, Dept Chem, Lab Phys Chim Mat & Electrolytes Energie PCM2E, Fac Sci,EA 6299, Ave Monge,Parc Grandmt, F-37200 Tours, France
[2] Univ Hassan II Casablanca, Lab Chim Phys & Chim Bioorgan, URAC 22 BP,146, Casablanca 28800, Mohammedia, Morocco
关键词
Click chemistry; Cross-coupling; CuAAC; Imidazo[1; 2-a]pyridine; One-pot synthesis; EFFICIENT SYNTHESIS; ZOLPIDEM; 1,2,3-TRIAZOLES; ALPIDEM; ACCESS; AGENTS; ACID;
D O I
10.1002/slct.202102228
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient one-pot regioselective synthesis of 2-(1,2,3-triazolyl)methyl-3-alkynyl imidazo[1,2-a]pyridines is reported under simple and mild reaction conditions. The new imidazo[1,2-a]pyridines embedded with 4-substituted-[1,2,3]-triazole were obtained in good to excellent yields from 2-(chloromethyl)-3-iodo imidazo[1,2-a]pyridines via a one-pot sequence involving an SN reaction with azide, followed by copper-catalyzed [3+2]cycloaddition and a Sonogashira coupling reaction.
引用
收藏
页码:9415 / 9420
页数:6
相关论文
共 34 条
[1]   Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].
Agalave, Sandip G. ;
Maujan, Suleman R. ;
Pore, Vandana S. .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718
[2]  
[Anonymous], 2014, ANGEW CHEM-GER EDIT, V126, P593
[3]   A novel approach for the identification of efficient combination therapies in primary human acute myeloid leukemia specimens [J].
Baccelli, I. ;
Krosl, J. ;
Boucher, G. ;
Boivin, I. ;
Lavallee, V-P ;
Hebert, J. ;
Lemieux, S. ;
Marinier, A. ;
Sauvageau, G. .
BLOOD CANCER JOURNAL, 2017, 7 :e529-e529
[4]  
Berson A, 2001, J PHARMACOL EXP THER, V299, P793
[5]   Imidazo[1,2-a]pyridin-3-amines as potential HIV-1 non-nucleoside reverse transcriptase inhibitors [J].
Bode, Moira L. ;
Gravestock, David ;
Moleele, Simon S. ;
van der Westhuyzen, Christiaan W. ;
Pelly, Stephen C. ;
Steenkamp, Paul A. ;
Hoppe, Heinrich C. ;
Khan, Tasmiyah ;
Nkabinde, Lindiwe A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (14) :4227-4237
[6]   Fused Tetrazoles as Azide Surrogates in Click Reaction: Efficient Synthesis of N-Heterocycle-Substituted 1,2,3-Triazoles [J].
Chattopadhyay, Buddhadeb ;
Vera, Claudia I. Rivera ;
Chuprakov, Stepan ;
Gevorgyan, Vladimir .
ORGANIC LETTERS, 2010, 12 (09) :2166-2169
[7]   Role of Zolpidem in the Management of Insomnia [J].
Dang, Amit ;
Garg, Amit ;
Rataboli, Padmanabh V. .
CNS NEUROSCIENCE & THERAPEUTICS, 2011, 17 (05) :387-397
[8]   Synthesis, Characterization, and in Vitro Evaluation of a New TSPO-Selective Bifunctional Chelate Ligand [J].
Denora, Nunzio ;
Margiotta, Nicola ;
Laquintana, Valentino ;
Lopedota, Angela ;
Cutrignelli, Annalisa ;
Losacco, Maurizio ;
Franco, Massimo ;
Natile, Giovanni .
ACS MEDICINAL CHEMISTRY LETTERS, 2014, 5 (06) :685-689
[9]   Medicinal attributes of 1,2,3-triazoles: Current developments [J].
Dheer, Divya ;
Singh, Virender ;
Shankar, Ravi .
BIOORGANIC CHEMISTRY, 2017, 71 :30-54
[10]   Olprinone Attenuates the Acute Inflammatory Response and Apoptosis after Spinal Cord Trauma in Mice [J].
Esposito, Emanuela ;
Mazzon, Emanuela ;
Paterniti, Irene ;
Impellizzeri, Daniela ;
Bramanti, Placido ;
Cuzzocrea, Salvatore .
PLOS ONE, 2010, 5 (09) :1-16