Copper-catalyzed three-component synthesis of 5-acetamidoimidazoles from carbodiimides, acyl chlorides and isocyanides?
Organic Chemistry Frontiers Pub Date: 2014-02-28 DOI: 10.1039/C4QO00034J
Abstract
Only very limited methods are available for the synthesis of 5-amino imidazoles. We report in this paper that three-component reaction of acyl chlorides, carbodiimides and α-isocyanoacetates or TosMIC took place smoothly in the presence of Et3N (2.5 equiv.) and a catalytic amount of copper iodide (0.2 equiv.) to afford 1,4-disubstituted 5-acetamidoimidazoles in good yields.
Recommended Literature
- [1] Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz JaremkoRSC Adv., 2020,10, 215-227 10.1039/C9RA09350H
- [2] An artificial CO-releasing metalloprotein built by histidine-selective metallation? Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?oChem. Commun., 2015,51, 3993-3996 10.1039/C4CC10204E
- [3] An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile? Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo NamDalton Trans., 2016,45, 376-383 10.1039/C5DT04292E
- [4] An amplified fluorescence detection of T4 polynucleotide kinase activity based on coupled exonuclease III reaction and a graphene oxide platform? Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao YouAnalyst, 2015,140, 1827-1831 10.1039/C4AN01953A
- [5] An amorphous lanthanum–iridium solid solution with an open structure for efficient water splitting? Wei Sun,Chenglong Ma,Xinlong Tian,Jianjun Liao,Ji Yang,Chengjun Ge,Weiwei HuangJ. Mater. Chem. A, 2020,8, 12518-12525 10.1039/D0TA03351K
- [6] An apparatus for determining small amounts of alchohol in sour milk and urine Analyst, 1964,89, 272-275 10.1039/AN9648900272
- [7] Aggregation-induced emission enhancement in halochalcones? Patricia A. A. M. Vaz,Jo?o Rocha,Artur M. S. SilvaNew J. Chem., 2016,40, 8198-8201 10.1039/C6NJ01387B
- [8] An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode Karl Crowley,Eimer O'Malley,Aoife Morrin,Malcolm R. Smyth,Anthony J. KillardAnalyst, 2008,133, 391-399 10.1039/B716154A
- [9] An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes Adeline Huiling Loo,Alessandra Bonanni,Martin PumeraAnalyst, 2013,138, 467-471 10.1039/C2AN36199J
- [10] Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties? S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. LeeRSC Adv., 2014,4, 23107-23115 10.1039/C4RA02318H
Journal Name:Organic Chemistry Frontiers
research_products
-
CAS no.: 89640-58-4