A Short Synthetic Route to 4,7‐Dihalogenated 1,10‐Phenanthrolines with Additional Groups in 3,8‐Position: Soluble Precursors for Macrocyclic Oligophenanthrolines
作者： Michael Schmittel , Horst Ammon
DOI: 10.1002/(SICI)1099-0690(199805)1998:5<785::AID-EJOC785>3.0.CO;2-#
关键词:
摘要: A short and efficient preparation of 3,8-dialkylated or 3,8-diarylated 1,10-phenanthrolines-4,7-diones is described. Their chlorination bromination furnishes the corresponding, highly soluble 4,7-dichloro- 4,7-dibromo phenanthrolines that constitute versatile precursors to macrocyclic oligophenanthrolines with exo-coordination sites. They can be further reacted by nucleophilic aromatic substitution Heck-coupling reactions.
sci-hub.se 参考文章(27)
Harry Sch�fer, Karl Gewald, Zur Synthese von 4-Aminochinolinen durch intramolekulareFriedel—Crafts-Reaktion Monatshefte Fur Chemie. ,vol. 109, pp. 527- 535 ,(1978) , 10.1007/BF00912769
Serafino Gladiali, Giorgio Chelucci, Franco Soccolini, Giovanna Delogu, Giovanna Chessa, Optically active phenanthrolines in asymmetric catalysis: II. Enantioselective transfer hydrogenation of acetophenone by rhodium/alkyl phenanthroline catalysts Journal of Organometallic Chemistry. ,vol. 370, pp. 285- 294 ,(1989) , 10.1016/0022-328X(89)87292-4
YOSHIHISA OKAMOTO, TAKEO UEDA, Preparation and Hydrolysis of 4-Amino-1H-1, 5-benzodiazepine-3-carbonitrile Chemical & Pharmaceutical Bulletin. ,vol. 23, pp. 1391- 1395 ,(1975) , 10.1248/CPB.23.1391
Thomas W. Bell, Lain Yen Hu, Sanjay V. Patel, Alkylation of heteroaryl halides by 2:1 Grignard reagent/copper(I) mixtures. Synthesis of alkylated octahydrodibenzo[b,j][1,10]phenanthrolines Journal of Organic Chemistry. ,vol. 52, pp. 3847- 3850 ,(1987) , 10.1021/JO00226A023
Michael Schmittel, Andrea Ganz, Synthesis of 4,7-Disubstituted Phenanthrolines as Key Building Blocks for the First Preparation of Macrocyclic Mono- and Bisphenanthrolines with exo-Coordination Sites Synlett. ,vol. 1997, pp. 710- 712 ,(1997) , 10.1055/S-1997-3243
Ulrich Lüning, Michael Müller, Markus Gelbert, Karl Peters, Hans Georg Von Schnering, Manfred Keller, Concave Reagents, 15[1]. New Concave 1,10‐Phenanthrolines: Catalysts for the Alcohol Addition to Ketenes and Ligands in Transition Metal Complexes Chemische Berichte. ,vol. 127, pp. 2297- 2306 ,(1994) , 10.1002/CBER.1491271131
Egle M. Beccalli, Concetta La Rosa, Alessandro Marchesini, Oxidation of 4-aryl-substituted isoxazolin-5-ones. A new synthesis of 2,5-diaryl-1,3-oxazin-6-ones Journal of Organic Chemistry. ,vol. 49, pp. 4287- 4290 ,(1984) , 10.1021/JO00196A034
Jan-Peter Spengler, Walter Schunack, H2-Antihistaminika, 18. Mitt. 5,6-Alkylsubstituierte 4-Pyrimidinone mit H2-antihistaminischer Wirkung Archiv Der Pharmazie. ,vol. 317, pp. 425- 430 ,(1984) , 10.1002/ARDP.19843170509
Peter C. Alford, Michael J. Cook, Anthony P. Lewis, Glenn S. G. McAuliffe, Vladimir Skarda, Andrew J. Thomson, John L. Glasper, David J. Robbins, Luminescent metal complexes. Part 5. Luminescence properties of ring-substituted 1,10-phenanthroline tris-complexes of ruthenium(II) Journal of The Chemical Society-perkin Transactions 1. ,vol. 16, pp. 705- 709 ,(1985) , 10.1039/P29850000705
Diego J. Cárdenas, Pablo Gaviña, Jean-Pierre Sauvage, Construction of Interlocking and Threaded Rings Using Two Different Transition Metals as Templating and Connecting Centers: Catenanes and Rotaxanes Incorporating Ru(terpy)2-Units in Their Framework Journal of the American Chemical Society. ,vol. 119, pp. 2656- 2664 ,(1997) , 10.1021/JA963955J