An expedient synthesis of 5-alkynyl-6-aryl-2,2′-bipyridines
作者： Maria I. Savchuk , Alexey P. Krinochkin , Alluru Rammohan , Albert F. Khasanov , Dmitry S. Kopchuk
DOI: 10.1016/J.MENCOM.2020.09.019
关键词:
摘要: 5-Alkynyl-6-aryl-2,2′-bipyridines were conveniently prepared in two steps comprising oxidative SN H ethynylation of 5-aryl-3-(2-pyridyl)-1,2,4-triazines at position 6. At the second step, 1,2,4-triazine moiety was transformed into pyridine one employing aza-Diels–Alder reaction with 2,5-norbornadiene.
sci-hub.st 参考文章(29)
Albert F. Khasanov, Dmitry S. Kopchuk, Igor S. Kovalev, Olga S. Taniya, Grigory V. Zyryanov, Vladimir L. Rusinov, Oleg N. Chupakhin, Reaction of lithium 2-arylethynides with 6-aryl-3-(2-pyridyl)-1,2,4-triazines as an access to 6-aryl-5-arylvinyl-3-(2-pyridyl)-1,2,4-triazines Mendeleev Communications. ,vol. 25, pp. 332- 333 ,(2015) , 10.1016/J.MENCOM.2015.09.003
Dmitry N. Kozhevnikov, Valery N. Kozhevnikov, Anton M. Prokhorov, Maria M. Ustinova, Vladimir L. Rusinov, Oleg N. Chupakhin, Grigory G. Aleksandrov, Burkhard König, Consecutive nucleophilic substitution and aza Diels–Alder reaction—an efficient strategy to functionalized 2,2′-bipyridines Tetrahedron Letters. ,vol. 47, pp. 869- 872 ,(2006) , 10.1016/J.TETLET.2005.12.006
F. Ivy Carroll, Sharadsrikar V. Kotturi, Hernán A. Navarro, S. Wayne Mascarella, Brian P. Gilmour, Forrest L. Smith, Bichoy H. Gabra, William L. Dewey, Synthesis and pharmacological evaluation of phenylethynyl[1,2,4]methyltriazines as analogues of 3-methyl-6-(phenylethynyl)pyridine. Journal of Medicinal Chemistry. ,vol. 50, pp. 3388- 3391 ,(2007) , 10.1021/JM070078R
E Birckner, U-W Grummt, AH Göller, T Pautzsch, DAM Egbe, M Al-Higari, E Klemm, None, Photophysics of Arylene and Heteroaryleneethinylenes Journal of Physical Chemistry A. ,vol. 105, pp. 10307- 10315 ,(2001) , 10.1021/JP010546N
Christine Goze, Denis V. Kozlov, Daniel S. Tyson, Raymond Ziessel, Felix N. Castellano, Synthesis and photophysics of ruthenium(II) complexes with multiple pyrenylethynylene subunits New Journal of Chemistry. ,vol. 27, pp. 1679- 1683 ,(2003) , 10.1039/B307327K
Valery N. Kozhevnikov, Olga V. Shabunina, Dmitry S. Kopchuk, Maria M. Ustinova, Burkhard König, Dmitry N. Kozhevnikov, Facile synthesis of 6-aryl-3-pyridyl-1,2,4-triazines as a key step toward highly fluorescent 5-substituted bipyridines and their Zn(II) and Ru(II) complexes Tetrahedron. ,vol. 64, pp. 8963- 8973 ,(2008) , 10.1016/J.TET.2008.06.040
José Vicente, Juan Gil-Rubio, Natalia Barquero, Peter G. Jones, Delia Bautista, Synthesis of Luminescent Alkynyl Gold Metalaligands Containing 2,2′-Bipyridine-5-yl and 2,2′:6′,2′′-Terpyridine-4-yl Donor Groups Organometallics. ,vol. 27, pp. 646- 659 ,(2008) , 10.1021/OM7009123
Anton M. Prokhorov, Mieczysław Mąkosza, Oleg N. Chupakhin, Direct introduction of acetylene moieties into azines by SNH methodology Tetrahedron Letters. ,vol. 50, pp. 1444- 1446 ,(2009) , 10.1016/J.TETLET.2009.01.070
Michito Shiotsuka, Yasuhiro Inui, Yasushi Sekioka, Youhei Yamamoto, Satoru Onaka, Synthesis, photochemistry, and electrochemistry of ruthenium(II) polypyridyl complexes anchored by dicobalt carbonyl units Journal of Organometallic Chemistry. ,vol. 692, pp. 2441- 2447 ,(2007) , 10.1016/J.JORGANCHEM.2007.02.014
Anton M. Prokhorov, Pavel A. Slepukhin, Dmitry N. Kozhevnikov, CuCl2 induced reactions of 6-ethynyl- and 6-cyano-5-aryl-2,2′-bipyridines with various N- and O-nucleophiles in comparison with the reactions of relative 1,2,4-triazines Journal of Organometallic Chemistry. ,vol. 693, pp. 1886- 1894 ,(2008) , 10.1016/J.JORGANCHEM.2008.02.016