PMID: 11929236Apr 4, 2002Paper

Selective syntheses of metalated pyridines from two different unsymmetrical acetylenes, a nitrile, and a titanium(II) alkoxide

Journal of the American Chemical Society
Daisuke SuzukiF Sato

Abstract

Cyclotrimerization of two different, unsymmetrical acetylenes and p-toluenesulfonylnitrile with a divalent titanium alkoxide reagent, Ti(O-i-Pr)4/2 i-PrMgCl, yielded single pyridyltitanium compounds in a highly selective manner. These metalated pyridines were confirmed by deuteriolysis to give the corresponding deuterated pyridines and underwent iodinolysis and copper-catalyzed alkylation to demonstrate their synthetic utility. Alternatively, a different type of cyclotrimerization of an alkynamide, terminal acetylenes, and alpha-alkoxynitriles mediated by the same titanium(II) alkoxide again proceeded in a highly selective manner to give single pyridines having a titanated side chain.

References


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Citations

Jan 12, 2013·Chemical Reviews·Anton V GulevichVladimir Gevorgyan
Mar 16, 2006·Chemical Communications : Chem Comm·Ramesh S SenaiarAlexander Deiters
May 24, 2006·Chemical Communications : Chem Comm·Vincent GandonMax Malacria
Jun 28, 2017·Israel Journal of Chemistry·Glenn C Micalizio, Haruki Mizoguchi
Jun 6, 2014·Chemical Communications : Chem Comm·V A RassadinY Six
Aug 10, 2007·Organic Letters·Takanobu SanjiMasato Tanaka
Apr 7, 2005·Journal of the American Chemical Society·Michael M McCormickJanis Louie
Sep 11, 2003·Chemical Reviews·Jesús A Varela, Carlos Saá
Nov 23, 2011·Journal of the American Chemical Society·Ming Z Chen, Glenn C Micalizio
Jan 13, 2012·Journal of the American Chemical Society·Stephen N GreszlerGlenn C Micalizio
Aug 12, 2017·The Journal of Organic Chemistry·Debayan SarkarHans Reuter
Oct 25, 2003·The Journal of Organic Chemistry·Jesús A VarelaCarlos Saá

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