Substituted 1,10-Phenanthroline-5,6-diamines and their Extension to Soluble, Acetylenic Pyrazinophenanthrolines

Abstract

2,9-Disubstituted and 3,8-disubstituted 1,10-phenanthrolines have been converted to the respective 5,6-diamines in three steps. The new heterocycles have been employed in condensation reactions with a protected 1,2-dialkynyl-1,2-dione to afford solubility-improved, acetylenic pyrazinophenanthrolines (pyzphen). In an initial study, the synthetic scope of these novel acetylenic ligands is evaluated.

Key words

acetylenes - condensation - ligands - solubility - synthesis

References

• For recent examples see:
• 3a Olson EJC. Hu D. Hörmann A. Jonkman AM. Arkin MR. Stemp EDA. Barton JK. Barbara PF. J. Am. Chem. Soc.  1997,  119:  11458 
• 3b Brennaman MK. Meyer TJ. Papanikolas JM. J. Phys. Chem. A  2004,  108:  9938 
• 3c Aldrich-Wright J. Brodie C. Glazer EC. Luedtke NW. Elson-Schwab L. Tor Y. Chem. Commun.  2004,  1018 
• 3d Rezvani A. Bazzi HS. Chen B. Rakotondradany F. Sleiman HF. Inorg. Chem.  2004,  43:  5112 
• 4 Delaney S. Pascaly M. Bhattacharya PK. Han K. Barton JK. Inorg. Chem.  2002,  41:  1966 
• 5 Guo X.-Q. Castellano FN. Li L. Lakowicz JR. Biophys. Chem.  1998,  71:  51 
• 6a Konduri R. Ye H. MacDonnell FM. Serroni S. Campagna S. Rajeshwar K. Angew. Chem. Int. Ed.  2002,  41:  3185 
• 6b Chiorboli C. Rodgers MAJ. Scandola F. J. Am. Chem. Soc.  2003,  125:  483 
• 6c Konduri R. Tacconi NRD. Rajeshwar K. MacDonnell FM. J. Am. Chem. Soc.  2004,  126:  11621 
• 7 Sun L. Hammarström L. Åkermark B. Styring S. Chem. Soc. Rev.  2001,  30:  36 
• 8 Ishow E. Gourdon A. Launay J.-P. Chiorboli C. Scandola F. Inorg. Chem.  1999,  38:  1504 
• 9a Schmittel M. Ammon H. Synlett  1997,  1096 
• 9b Schmittel M. Ammon H. Eur. J. Org. Chem.  1998,  785 
• 10a Ziessel R. Stroh C. Tetrahedron Lett.  2004,  45:  4051 
• 10b Loren JC. Siegel JS. Angew. Chem. Int. Ed.  2001,  40:  754 
• 10c Joshi HS. Jamshidi R. Tor Y. Angew. Chem. Int. Ed.  1999,  38:  2721 
• 10d Toyota S. Woods CR. Benaglia M. Siegel JS. Tetrahedron Lett.  1998,  39:  2697 
• 10e Connors PJ. Tzalis D. Dunnick AL. Tor Y. Inorg. Chem.  1998,  37:  1121 
• 10f Belser P. Bernhard S. Guerig U. Tetrahedron  1996,  52:  2937 
• For recent examples see:
• 11a Schmittel M. Michel C. Wiegrefe A. Synthesis  2005,  367 
• 11b Kalsani V. Ammon H. Jackel F. Rabe JP. Schmittel M. Chem. Eur. J.  2004,  5481 
• 11c Schmittel M. Kalsani V. Fenske D. Wiegrefe A. Chem. Commun.  2004,  490 
• 11d Schmittel M. Ammon H. Kalsani V. Wiegrefe A. Michel C. Chem. Commun.  2002,  2566 
• 11e Grave C. Schlüter AD. Eur. J. Org. Chem.  2002,  3075 
• 11f Schmittel M. Michel C. Wiegrefe A. Kalsani V. Synthesis  2001,  1561 
• 11g Schmittel M. Ammon H. Synlett  1999,  750 
• 12 Faust R. Ott S. J. Chem. Soc., Dalton Trans.  2002,  1946 
• 13 Ott S. Faust R. Chem. Commun.  2004,  388 
• 14 Dietrich-Buchecker CO. Marnot PA. Sauvage J.-P. Tetrahedron Lett.  1982,  50:  5291 
• 15 Chardon-Noblat S. Sauvage J.-P. Tetrahedron  1991,  47:  5123 
• 16 Santangelo F. Casagrande C. Miragoli G. Vecchietti V. Eur. J. Med. Chem.  1994,  29:  877 
• 17 Croisy M. Huel C. Bisagni E. Heterocycles  1997,  45:  683 
• 18 Yamada M. Tanaka Y. Yoshimoto Y. Kuroda S. Shimao I. Bull. Chem. Soc. Jpn.  1992,  65:  1006 
• 19 Bodige S. MacDonnell FM. Tetrahedron Lett.  1997,  38:  8159 
• 20 Faust R. Weber C. Fiandanese V. Marchese G. Punzi A. Tetrahedron  1997,  53:  14655 
• 21 Behr OM. Eglinton G. Galbraith AR. Raphael RA. J. Chem. Soc.  1960,  3614 

1

New Address: Dr. S. Ott, Institute of Chemistry, Department of Organic Chemistry, BMC, Uppsala University, Box 599, 75124 Uppsala, Sweden, Fax: [phone], E-Mail: [e-mail].

2

New Address: Prof. Dr. R. Faust, Institute of Chemistry, Faculty of Physical Sciences, University of Kassel, Heinrich-Plett-Str. 40, 34132 Kassel, Germany, Fax: [phone], E-Mail: [e-mail].