Synthesis and NMR Analysis of 1,4-Disubstituted 1,2,3-Triazoles Tethered to Pyridine, Pyrimidine, and Pyrazine Rings†
作者： Aljoša Bolje , Damijana Urankar , Janez Košmrlj
关键词: Two-dimensional nuclear magnetic resonance spectroscopy 、 Coupling reaction 、 Cycloaddition 、 Pyridine 、 Nuclear magnetic resonance spectroscopy 、 Organic chemistry 、 Pyrazine 、 Alkyne 、 Chemistry 、 Combinatorial chemistry 、 Click chemistry
摘要: A combinatorial modular approach based on the “click” copper(I)-catalysed azide–alkyne cycloaddition reaction was used to prepare a library of selected 1,4-disubstituted 1,2,3-triazoles differently functionalized with heteroaryl groups including pyridine, pyrimidine, and pyrazine. Three different copper(I) sources, i.e., CuSO4/sodium ascorbate, CuBr(PPh3)3, (CuOTf)2·C6H6 were promote coupling reactions range aryl, heteroaryl, heteroarylmethyl azides alkyne partners. As target triazoles designed serve as advanced ligands or ligand precursors for metal coordination, they fully characterized by 1H, 13C, 15N NMR spectroscopy. The resonances assigned basis 1D 2D experiments. 1H–15N gs-HMBC practical tool determine chemical shifts at natural abundance level isotope.
sci-hub.se 参考文章(79)
Benjamin R. Buckley, Harry Heaney, Mechanistic Investigations of Copper(I)-Catalysed Alkyne–Azide Cycloaddition Reactions ChemInform. ,vol. 44, pp. 1- 29 ,(2012) , 10.1007/7081_2011_71
Roland Kleinmaier, Sven Arenz, Alavi Karim, Anna‐Carin C Carlsson, Máté Erdélyi, None, Solvent effects on 15N NMR coordination shifts. Magnetic Resonance in Chemistry. ,vol. 51, pp. 46- 53 ,(2013) , 10.1002/MRC.3907
Christian W. Tornøe, Caspar Christensen, Morten Meldal, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry. ,vol. 67, pp. 3057- 3064 ,(2002) , 10.1021/JO011148J
Liam P. Spencer, Ramadan Altwer, Pingrong Wei, Lucio Gelmini, James Gauld, Douglas W. Stephan, Pyridine− and Imidazole−Phosphinimine Bidentate Ligand Complexes: Considerations for Ethylene Oligomerization Catalysts Organometallics. ,vol. 22, pp. 3841- 3854 ,(2003) , 10.1021/OM030311T
Tadashi Sasaki, Ken Kanematsu, Masayoshi Murata, Heteroaromaticity. XLIX. Tetrazolo-azido isomerization in heteroaromatics. I. Syntheses and reactivities of some tetrazolopolyazines Journal of Organic Chemistry. ,vol. 36, pp. 446- 449 ,(1971) , 10.1021/JO00802A017
Damijana Urankar, Balazs Pinter, Andrej Pevec, Frank De Proft, Iztok Turel, Janez Košmrlj, Click-triazole N2 coordination to transition-metal ions is assisted by a pendant pyridine substituent. Inorganic Chemistry. ,vol. 49, pp. 4820- 4829 ,(2010) , 10.1021/IC902354E
Ranfeng Sun, Huangdong Wang, Jianfeng Hu, Jiudong Zhao, Hao Zhang, Pyridine-phosphinimine ligand-accelerated Cu(I)-catalyzed azide–alkyne cycloaddition for preparation of 1-(pyridin-2-yl)-1,2,3-triazole derivatives Organic and Biomolecular Chemistry. ,vol. 12, pp. 5954- 5963 ,(2014) , 10.1039/C4OB01176G
Maikel Wijtmans, Sylvain Celanire, Erwin Snip, Michel R. Gillard, Edith Gelens, Philippe P. Collart, Bastiaan J. Venhuis, Bernard Christophe, Saskia Hulscher, Henk van der Goot, Florence Lebon, Henk Timmerman, Remko A. Bakker, Bénédicte I. L. F. Lallemand, Rob Leurs, Patrice E. Talaga, Iwan J. P. de Esch, 4-Benzyl-1H-imidazoles with Oxazoline Termini as Histamine H3Receptor Agonists Journal of Medicinal Chemistry. ,vol. 51, pp. 2944- 2953 ,(2008) , 10.1021/JM7014149
David Schweinfurth, Naina Deibel, Fritz Weisser, Biprajit Sarkar, Mit Klick zu neuen Liganden Nachrichten Aus Der Chemie. ,vol. 59, pp. 937- 941 ,(2011) , 10.1002/NADC.201190062
Harriet Struthers, Thomas L. Mindt, Roger Schibli, Metal chelating systems synthesized using the copper(I) catalyzed azide-alkyne cycloaddition. Dalton Transactions. ,vol. 39, pp. 675- 696 ,(2010) , 10.1039/B912608B