Editing Terpyridine (section)

==Synthesis==
Terpyridine was first synthesized by G. Morgan and F. H. Burstall in 1932 by the [[oxidative coupling]] of pyridines. This method, however, proceeded in low yields.  More efficient syntheses have since been described, mainly starting from [[2-acetylpyridine]].<ref>{{cite journal | last1 = Hofmeier | first1 = H. | last2 = Schubert | first2 = U. S. | year = 2004 | title = Recent developments in the supramolecular chemistry of terpyridine-metal complexes | journal = Chem. Soc. Rev. | volume = 33 | issue = 6| pages = 373–99 | doi = 10.1039/B400653B | pmid = 15280970 }}</ref> One method produces an enaminone by the reaction of 2-acetylpyridine with [[N,N-dimethylformamide]] dimethyl [[acetal]].<ref>{{cite book | last1 = Jameson | first1 = Donald L. | last2 = Guise | first2 = Lisa E. | chapter = 2,2′:6′,2″-Terpyridine | year = 1998 | title = Inorganic Syntheses | volume = 32 | pages = 46–50 | doi = 10.1002/9780470132630.ch7 | isbn = 978-0-471-24921-4 }}</ref>  The base-catalyzed reaction of 2-acetylpyridine with [[carbon disulfide]] followed by alkylation with [[methyl iodide]] gives C<sub>5</sub>H<sub>4</sub>NCOCH=C(SMe)<sub>2</sub>.  Condensation of this species with 2-acetylpyridine forms the related 1,5-diketone, which condenses with [[ammonium acetate]] to form a terpyridine.  Treatment of this derivative with [[Raney nickel]] removes the [[thioether]] group.<ref>{{ OrgSynth | author = Potts, K. T.; Ralli, P.; Theodoridis, G.; Winslow, P. | title = 2,2':6',2' - Terpyridine | collvol = 7 | collvolpages = 476 | year = 1990 | prep = cv7p0476 }}</ref>

Other methods have been developed for the synthesis of terpyridine and its substituted derivatives.<ref>Kamata, K., Suzuki, A., Nakai, Y., Nakazawa, H., "Catalytic Hydrosilylation of Alkenes by Iron Complexes Containing Terpyridine Derivatives as Ancillary Ligands", Organometallics 2012, 31, 3825. {{doi|10.1021/om300279t}}</ref>  Substituted terpyridines are also synthesized from [[palladium]]-catalyzed cross-coupling reactions. It can be prepared from [[bis-triazinyl pyridine]].