Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2003(13): 2096-2100
DOI: 10.1055/s-2003-41452
DOI: 10.1055/s-2003-41452
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Facile Route to Symmetrical and Unsymmetrical Cycloalkeno[c]fused 2,2′-Bipyridine Ligands via Inverse Electron Demand Diels-Alder Reaction of 5,5′-bi-1,2,4-Triazines [1]
Further Information
Received
7 March 2003
Publication Date:
10 September 2003 (online)
Publication History
Publication Date:
10 September 2003 (online)
![](https://www.thieme-connect.de/media/synthesis/200313/lookinside/thumbnails/10.1055-s-2003-41452-1.jpg)
Abstract
A series of 6,6′-bisfunctionalized symmetrical cycloalkeno[c]fused 2,2′-bipyridines 4a-h or unsymmetrical cycloalkeno[c]fused 2,2′-bipyridines 6a-g is described. They were prepared by the Diels-Alder reaction of 3,3′-disubstituted 5,5′-bi-1,2,4-triazines 2a,b with cyclic enamines 3a-d. The regioselective reaction of 1-vinylimidazole (3e) with 2a leads to 5-(2-pyridyl)-1,2,4-triazine 9 which undergoes Diels-Alder reaction with cyclic enamines 3a-d to give unsymmetrical 2,2′-bipyridines 10a-d with one cycloalkene ring attached.
Key words
Diels-Alder reactions - annulenes - pyridines
- 1 Part 20 in 1,2,4-Triazines in Organic Synthesis. For part 19, see:
Lipinska T. Tetrahedron Lett. 2002, 43: 9565 -
2a
Lehn J.-M. Supramolecular Chemistry, Concepts and Perspectives VCH; Weinheim: 1995. -
2b
Kaes C.Katz A.Hosseini MW. Chem. Rev. 2000, 100: 3553 - 3
Schubert US.Eschbaumer C. Angew. Chem. Int. Ed. 2002, 41: 2892 -
4a
Pomeranc D.Heitz V.Chambron J.-C.Savage J.-P. J. Am. Chem. Soc. 2001, 123: 12215 -
4b
Demadis KD.Hartshorn CM.Meyer TJ. Chem. Rev. 2001, 101 -
5a
Keefe MH.Benkstein KD.Hupp JT. Coord. Chem. Rev. 2000, 205: 201 -
5b
Beer PD.Cadman J. Coord. Chem. Rev. 2000, 205: 131 - 6
Pietraszkiewicz M.Karpiuk J.Pietraszkiewicz O. Spectrochim. Acta, Part A 1998, 54: 2229 ; and references cited therein - 7
Pietraszkiewicz M. Comrehensive Supramolecular Chemistry, Luminescent Probes Vol. 10:Lehn J.-M.Kaes C.Katz A.Hosseini M. Pergamon; Oxford: 1996. p.225 - 8
Steel PJ. Adv. Heterocycl. Chem. 1997, 67: 1 -
9a
Ito K.Tabuchi S.Katsuki T. Synlett 1992, 575 -
9b
Ito K.Katsuki T. Tetrahedron Lett. 1993, 34: 2661 -
9c
Ito K.Yoshitake M.Katsuki T. Tetrahedron 1996, 52: 3905 -
10a
Kolp B.Abeln D.Stoeckli-Evans H.Von Zalewsky A. Eur. J. Inorg. Chem. 2001, 1207 -
10b
Von Zalewsky A.Mamula O. J. Chem. Soc. Dalton Trans. 2000, 219 ; and references cited therein - 11
Varella JA.Castedo L.Maestro M.Mahia J.Saci C. Chem.-Eur. J. 2001, 7: 5203 - 12
Bushby M.Moody CJ.Riddick DA.Waldron IR. J. Chem. Soc., Perkin Trans. 1 2001, 2183 - 13
Rykowski A.Branowska D.Kielak J. Tetrahedron Lett. 2000, 41: 3657 - 14
Rickborn B. In Organic Reactions Vol. 53:Paquette LA. John Wiley and Sons; New York: 1998. p.493 - 15
Neunhoeffer H.Lehmann B. Liebigs Ann. Chem. 1977, 1413 - 16
Branowska D.Rykowski A. Synlett 2002, 1892 - 17
Krass DK.Chen T.-K.Paudler WW. J. Heterocycl. Chem. 1973, 10: 343 - 18
Boger DL.Weinreb SN. Hetero Diels-Alder Methodology in Organic SynthesisWasserman HH. Academic Press; New York: 1987. -
19a
Baret P.Einhorn J.Gellon G.Pierre J.-L. Synthesis 1998, 431 -
19b
Mürner H.Von Zalewsky A.Stoeckli-Evans H. Inorg. Chem. 1996, 35: 3931 - 20
Fletcher NC. J. Chem. Soc., Perkin Trans. 1 2002, 1831 -
21a
Barlow MG.Haszeldine RN.Simpkin DJ. J. Chem. Soc., Chem. Commun. 1979, 658 -
21b
Sagi M.Amano M.Konno S.Yamanaka H. Heterocycles 1989, 29: 2249 -
21c
Pabst GR.Pfüller OC.Sauer J. Tetrahedron 1999, 55: 5047 -
21d
Pabst GR.Sauer J. Tetrahedron 1999, 55: 5067 -
21e
Neunhoeffer H. In Comprehensive Heterocyclic Chemistry II, 1,2,4-Triazines and their Benzo Derivatives Vol. 5:Katritzky AR.Rees CW.Scriven EF. Pergamon Press; NY: 1996. p.507 ; and subsection -
21f
Sauer J. In Comprehensive Heterocyclic Chemistry II, Tetrazines Vol. 6:Katritzky AR.Rees CW.Scriven EF. Pergamon Press; NY: 1996. p.901 - 22
Perrin DD.Armarego WLF. Purification of Laboratory Chemicals Pergamon; NY: 1992. -
23a
Krass DK.Chen TK.Paudler WW. J. Heterocycl. Chem. 1973, 10: 343 -
23b
Krass DK.Chen TK.Paudler WW. J. Heterocycl. Chem. 1974, 11: 43 -
23c
Neunhoeffer H.Frühauf HW. Liebigs Ann. Chem. 1972, 102-103: 760