Highly Versatile Synthetic Approach to Oligopyridines and Derivatives by Kröhnke-type Ring-closure Reactions

Daniel Caterbow and Ulrich Ziener^@

University of Ulm, Institute of Organic Chemistry III, Albert-Einstein-Allee 11, D-89081 Ulm, Germany

^@Corresponding author E-mail: ulrich.ziener@uni-ulm.de

Macroheterocycles 2011 4(4) 249-264

DOI: 10.6060/mhc2011.4.04

Received 16.08.2011
Accepted 20.09.2011

The synthesis of a large variety of different conjugated oligopyridines and derivatives with electron poor and/or rich
peripheral substituents and with pyridine and other (hetero)aromatic cores by the highly versatile Kröhnke-type
synthesis is described. Simple electronic and steric considerations of the participating unsaturated ketones (chalcones)
allow a rough estimation of the synthetic accessibility of the desired compounds.

MHC2011_t04n04_249-264.pdf (1,54 MB)

References

Click here to expand or collapse this section

1. a) R. A. Fallahpour, Curr. Org. Synth. 2006, 3, 19-39;
http://dx.doi.org/10.2174/157017906775473957
b) E. C. Constable, in Prog. Inorg. Chem., Vol. 42 (Ed.: K. D. Karlin), Wiley-Interscience, 1994, pp. 67-138;
http://dx.doi.org/10.1002/9780470166437.ch2
c) E. C. Constable, in Advances in Inorganic Chemistry and Radiochemistry, Vol. 30 (Eds.: H. J. Emeleus, A. G. Sharpe), Academic Press, New York, 1986, pp. 69-121;
d) K. T. Potts, Bull. Soc. Chim. Belg. 1990, 99, 741-768.
http://dx.doi.org/10.1002/bscb.19900990911

2. a) G. R. Pabst, K. Schmid, J. Sauer, Tetrahedron Lett. 1998, 39, 6691-6694;
http://dx.doi.org/10.1016/S0040-4039(98)01438-5
b) G. R. Pabst, J. Sauer, Tetrahedron Lett. 1998, 39, 6687-6690.
http://dx.doi.org/10.1016/S0040-4039(98)01437-3

3. K. T. Potts, M. J. Cipullo, P. Ralli, G. Theodoridis, J. Org. Chem. 1982, 47, 3027-3038.
http://dx.doi.org/10.1021/jo00137a001

4. F. Kröhnke, Synthesis 1976, 1-24 http://dx.doi.org/10.1055/s-1976-23941.

5. a) U. Ziener, J.-M. Lehn, A. Mourran, M. Möller, Chem.-Eur. J. 2002, 8, 951-957;
http://dx.doi.org/10.1002/1521-3765(20020215)8:4<951::AID-CHEM951>3.0.CO;2-9
b) U. Ziener, J. Phys. Chem. B 2008, 112, 14698-14717;
http://dx.doi.org/10.1021/jp805846d
c) C. Meier, U. Ziener, K. Landfester, P. Weihrich, J. Phys. Chem. B 2005, 109, 21015-21027;
http://dx.doi.org/10.1021/jp054271d
d) D. Caterbow, D. Künzel, M. G. Mavros, A. Groß, K. Landfester, U. Ziener, Beilstein J. Nanotechnol. 2011, 2, 405-415.

6. a) D. Caterbow, U. Ziener, Chem. Comm. 2011, 9366-9368;
http://dx.doi.org/10.1039/c1cc13526k
b) D. Caterbow, M. Roos, H. E. Hoster, R. J. Behm, K. Landfester, U. Ziener, Chem.-Eur. J. 2011, 17, 7831-7836.
http://dx.doi.org/10.1002/chem.201003319

7. a) C. Meier, M. Roos, D. Künzel, A. Breitruck, H. Hoster, K. Landfester, A. Gross, R. J. Behm, U. Ziener, J. Phys. Chem. C 2010, 114, 1268-1277;
http://dx.doi.org/10.1021/jp910029z
b) C. Meier, K. Landfester, U. Ziener, J. Phys. Chem. C 2009, 113, 1507-1514;
http://dx.doi.org/10.1021/jp808431t
c) C. Meier, K. Landfester, U. Ziener, J. Phys. Chem. C 2008, 112, 15236-15240;
http://dx.doi.org/10.1021/jp804235a
d) C. Meier, K. Landfester, D. Künzel, T. Markert, A. Groß, U. Ziener, Angew. Chem. Int. Ed. 2008, 47, 3821-3825;
http://dx.doi.org/10.1002/anie.200705527
e) H. E. Hoster, M. Roos, A. Breitruck, C. Meier, K. Tonigold, T. Waldmann, U. Ziener, K. Landfester, R. J. Behm, Langmuir 2007, 23, 11570-11579;
http://dx.doi.org/10.1021/la701382n
f) Y. Dai, C. Meier, U. Ziener, K. Landfester, C. Täubert, D. M. Kolb, Langmuir 2007, 23, 11058-11062.
http://dx.doi.org/10.1021/la701479r

8. Y. Jahng, L.-X. Zhao, Y.-S. Moon, A. Basnet, E.-k. Kim, H. W. Chang, H. K. Ju, T. C. Jeong, E.-S. Lee, Biorg. Med. Chem. Lett. 2004, 14, 2559–2562.
http://dx.doi.org/10.1016/j.bmcl.2004.02.099

9. Z. Zhang, Y.-W. Dong, G.-W. Wang, Chem. Lett. 2003, 32, 966-967.
http://dx.doi.org/10.1246/cl.2003.966

10. J. Durinda, L. Szucs, L. Krasnec, J. Heger, V. Springer, J. Kolena, J. Keleti, Acta Fac. Pharm. Bohem. 1966, 12, 89-129.

11. A. Basnet, P. Thapa, R. Karki, Y. Na, Y. Jahng, B.-S. Jeong, T. C. Jeong, C.-S. Lee, E.-S. Lee, Bioorg. Med. Chem. 2007, 15, 4351-4359.
http://dx.doi.org/10.1016/j.bmc.2007.04.047

12. M. L. J. Mihailovic, M. Tot, J. Org. Chem. 1957, 22, 652-654.
http://dx.doi.org/10.1021/jo01357a017

13. L. Krasnec, J. Durinda, L. Szücs, Chem. Zvesti 1961, 15, 558-562.

14. A. Ullah, F. L. Ansari, Ihsan-ul-Haq, S. Nazir, B. Mirza, Chem. Biodivers. 2007, 4, 203-214.
http://dx.doi.org/10.1002/cbdv.200790025

15. N. H. Crommwell, R. P. Cahoy, W. E. Franklin, G. D. Mercer, J. Am. Chem. Soc. 1957, 79, 922-925.
http://dx.doi.org/10.1021/ja01561a039

16. T. P. Robinson, R. B. Hubbard IV, T. J. Ehlers, J. L. Arbiser, D. J. Goldsmith, J. P. Bowen, Bioorg. Med. Chem. 2005, 13, 4007-4013.
http://dx.doi.org/10.1016/j.bmc.2005.03.054

17. Y. Xin, Z.-H. Zang, F.-L. Chen, Synth. Commun. 2009, 39, 4062-4068.
http://dx.doi.org/10.1080/00397910902883686

18. P. Kadjane, L. Charbonnière, F. Camerel, P. P. Lainé, R. Ziessel, J. Fluoresc. 2008, 18, 119-129.
http://dx.doi.org/10.1007/s10895-007-0250-9

19. M. Cussac, A. Boucherle, Chim. Ther. 1967, 2, 101-105.

20. A. Stroba, F. Schaeffer, V. Hindie, L. Lopez-Garcia, I. Adrian, W. Fröhner, R. W. Hartmann, R. M. Biondi, M. Engel, J. Med. Chem. 2009, 52, 4683-4693.
http://dx.doi.org/10.1021/jm9001499

21. M. G. Mamolo, D. Zampieri, V. Falagiani, L. Vio, E. Banfi, Farmaco 2001, 56, 593-600.
http://dx.doi.org/10.1016/S0014-827X(01)01098-9

22. C. Meier, Dissertation thesis, University of Ulm (Ulm), 2008.

Attachment	Size
MHC2011_t04n04_249-264.pdf	1.54 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search